So often, I hear women say they’re struggling to get dressed and put outfits together, and lately, I’ve been feeling much the same way. Even though I rebuild my wardrobe every season because of this blog, it doesn’t always come together easily. You’d think I’d have it down by now, but even with all the practice I’ve had, it still takes time to make everything work together. The beginning of each season usually takes some time before I find my rhythm, and this year it’s taking longer than usual.
I’m sure being away in Europe for over two weeks in September didn’t help, and even though it’s mid-October, we haven’t had much real fall weather yet here in Philly, so I haven’t had many opportunities to wear true fall outfits—at least not beyond what I’ve styled for content. And while those looks are fun to shoot, they don’t always fit my everyday life. When it comes to getting dressed for my actual day-to-day, I’ve been struggling. So here’s what I’m doing to fix it.
1. Create Reliable Denim + Shoe Combos
Michael Stars Nara Mock Neck Top (M) // FRAME Lax Flares (30) // Veronica Beard Kelby (8.5) // FRAME Twist Buckle Belt (M) // Jenny Bird hoops
For starters, I realized I don’t have enough reliable denim-and-shoe pairings. I wear jeans almost every day, and when the proportions or hems don’t work with the shoes in my closet, it limits how many outfits I can put together—and the process becomes frustrating.
Right now, a lot of my jeans are too long for the shoes in my closet. I either need to have the jeans altered or buy shoes with higher heels. I’ve been trying to avoid tailoring, so I ordered a few pairs of boots with higher heels, but that led me to my next realization…
Lesson: Every workable wardrobe needs a good variety of reliable denim-and-shoe combinations.
2. Align My Wardrobe with My Real Life
London Fog raincoat (S) // EVEREVE sweater vest (M) // PAIGE Anessa jeans (29) // Jeffrey Campbell flats (8.5) // Mulberry Amberley // Jenny Bird hoops // Baublebar necklace
My life is very casual these days, so when I’m getting dressed for my everyday, I’m almost always reaching for flats or sneakers. Even most of my boots have lower heels because that’s what’s available right now, and it’s what makes the most sense for my lifestyle.
Buying higher heels to make my longer jeans work didn’t solve the problem; it just made getting dressed even more frustrating. That was when I realized my closet doesn’t accurately reflect my current lifestyle. I’m always encouraging others to build wardrobes that fit their real, everyday lives, but in my case, I’d been buying too many pieces that don’t make sense for mine right now.
I have lots of cute going-out tops and longer jeans meant for heeled shoes, but the truth is, I don’t dress up much these days—and lower heels are trending anyway. So the day before I left on this trip, I grabbed a couple of those too-long jeans and took them to Nordstrom to have them shortened. It’s a pain, yes, and I hate waiting to get them back, but I wasn’t able to wear them anyway. Once they’re the right length for my everyday shoes, getting dressed will feel so much easier.
Lesson: The best wardrobes reflect the life you’re living right now—not the one you used to have (or the one you wish you had).
3. Add Everyday Tops That Work for Real Life
VEJA Esplar (39) // AG Mari (30) // Taylor Sweatshirt (last year) // similar camera bag
This ties right into the last point, but it’s another piece of the puzzle as I work toward a more functional fall wardrobe. Once I started paying attention, I realized it wasn’t just my jeans and shoes that were out of sync—there were other gaps too.
I mentioned above that I have a good assortment of “going-out” tops but very few everyday tops I actually want to wear while working from home or running errands. Maybe for you it’s something else—work pants, sweaters, or outer layers—but the idea is the same. We tend to focus on the fun, statement pieces and forget to replenish the simple ones that make our wardrobes truly wearable.
My graphic tees from summer aren’t cutting it now that the weather’s cooler, and I’ve realized I’m missing those “beyond basic” sweatshirts or elevated casual tops—the kind that feel more relaxed than a sweater but still pulled-together. In past seasons, I’ve had some great ones but passed them along (occupational hazard!).
So when I went to the mall to drop off my jeans at Nordstrom for hemming, I also stopped into Evereve—the best place I’ve found for the kind of casual tops I have in mind. I found a couple of good ones… more coming in tomorrow’s try-on haul!
Lesson: Don’t overlook the pieces you reach for most—they’re what make your wardrobe truly wearable.
4. Find the Right Tops to Wear Under Jackets
EVEREVE Bobbie Jacket (S) // LNA Harrison Tee (M) // MOTHER Hustler Roller Sneak (30) // Sam Edelman Saige (8.5)
I love to wear casual, lightweight jackets in the fall, and I’ve found a couple of good ones, but this year I’ve been struggling to find the right tops to wear underneath. What’s trending right now are fitted, cropped tees and bodysuits meant to tuck into high-rise jeans to create those sleek, smooth lines—but that silhouette doesn’t work particularly well for my proportions. And to be honest, those styles don’t feel great when I’m already feeling a little self-conscious about the extra fluff around my midsection. I prefer not to draw attention there—especially if there’s a chance I’ll take the jacket off.
To try and solve this, I ordered this ribbed tee to go with the Bobbie Jacket I’m wearing above (and the Avery Barn Jacket), but I don’t love it for times when I plan to take the jacket off. It’s a great tee—soft, good quality, and well-made—but it’s also quite form-fitting, which doesn’t do me any favors. So I’m keeping an eye out for tops that are shorter and cut closer to the body without being super tight or cropped.
It’s a tricky balance, because the key to layering under jackets is finding something thin enough not to add bulk but still flattering on its own. That’s what I’m looking for—tops that work with my jackets, not just under them.
Lesson: The right layering pieces make your favorite statement jackets more wearable—and they should look good on their own, too.
5. Focus on Fit
Z Supply Stella Henley (M) // PAIGE Anessa 31″ (29) // adidas SL 72 (8)
Speaking of fit… to be completely transparent, I’ve put on a few pounds since my trip, and some of my favorite jeans just aren’t comfortable right now. Plus, I’m self-conscious about the tighter-fitting tops that seem to be the current look, as mentioned above. This makes it harder to find pieces that feel current and work for my body right now.
It’s frustrating when current trends don’t work for my body or lifestyle, especially with the job I do, but I’m sure many of you can relate. Instead of opting out entirely, I’m trying to find pieces with a similar look that feel better for me—more forgiving but still modern. I know they’re out there; it’ll just take a little extra effort to track them down.
Lesson: You don’t have to follow every trend to the letter; the best pieces are often the ones that interpret it in a way that works for you.
I may also need to size up in a few pairs of jeans, but for now, I’m giving myself some grace and will reassess in a couple of weeks. I’ve put the tighter jeans in the back of my closet and am focusing on styling what fits. (It’ll be easier when I get those shortened jeans back!) Once I feel more like myself again, whether that means tweaking my routine or just adjusting my mindset, I’ll reassess.
Lesson: A great outfit starts with clothes that fit your body today—not last year’s version of it.
Final Thoughts
Every season comes with its own challenges, and sometimes it just takes a little recalibrating. Once I have a few of these pieces in place, I know I’ll find my groove again.
If you’re struggling to get dressed right now too, you’re not alone. Take a little time to reassess what’s working (and what’s not), fill in a few key gaps, and give yourself some grace along the way.
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96 Responses
This post really resonated with me. I too am struggling with what to wear, especially tops. They all seem to be VERY fitted and cropped. I look forward to seeing what you find as a good compromise, more forgiving but still modern (I love this). Thank you for sharing all of your knowledge!
I like the comment clothes need to fit your body today. Yep, and that can change on a daily basis sadly. That’s why I have different sizes in my closet and too many clothes. Good advise.
Great post! Your insights really resonated with me.
So relatable! The shoes/jeans or pants combo is killing me these days. And I’ve noticed in the last couple of weeks that I don’t have enough tops that aren’t cashmere or other sweaters so I’ve been trying to find some new options to add. It doesn’t help that I live in Georgia and our fall weather is so dang hot and it makes me grumpy lol. The other issue I have identified recently is that I don’t have enough color variety in my closet. I love the deep brown color that is trending and I find myself drawn to it every time I’m making a purchase. Otherwise I still have lots of black and gray from previous years. But every time I go to purchase something new, I don’t feel drawn to any of the other colors even though I recognize that I should branch out. I am not a capsule wardrobe sort of gal…I like variety! So I’ve got to figure out a fix for my color rut. Thanks for sharing your struggles! It at least helps to know I’m not alone. 🙂
Great suggestions JoLynne! I am in the same boat as you, more casual outfits, a few added pounds. Its so hard to give ourselves grace, but we need to! Looking forward to your evereve finds!
Jo-Lynne, as always I appreciate your transparency! Great post with lots of sound advice.
Omg! What a great post. Nice to know we all suffer with the same issues. I hope your new shorter jeans help with the stress your going through yourself. Take Care! The pounds will come off,think of all the great food you had on your trip that’s the culprit.
As i have aged and my body has changed, i am trying different styles. I no longer want to wear tight tops. I am loving more flowy tops that actually look more slimming-if you style it correctly.
I have never commented before but today I have to say this is one of the most helpful posts I’ve ever read! Thank you so much.
I feel this! I’ve been guilty of “aspirational shopping,” as if the version of me that would wear a dressy outfit is somehow better than the real version of me who prefers realistic, comfortable clothes.
I’m also really struggling with a lot of current trends and how they are particularly unflattering on my body. My lower belly pudge refuses to leave no matter how much weight I lose, and the shorter-length shirts and sweaters and jackets so often hit *right* where I’m widest. I also look like some sort of mutant in a lot of wide leg styles.
I appreciate your honesty and how real you are, and I’ve learned so much from reading your blog! For what it’s worth, your more casual looks are by far my favorite and the most relatable for me, so I’m here for the sneakers, sweatshirts, and kitten heels!
Love that term “aspirational shopping!” I’m guilty of it too!
“Aspirational shopping” and the belly pudge that won’t budge. If that doesn’t describe me to a tee! So relatable as is this post!
JoLynne, I really appreciate this post. I feel the same way! I love fall clothing and all the cute pants and dresses, but the truth is, I rarely wear them. It’s nice to hear you understand that! Thank you for introducing me to Ever Eve. I love their clothing and it’s different from what you find in other stores. Keep up the good work!
Jo-Lynne, thank you so much for your candor. This article really hits home as I am a 55 year old woman tired of trying in vain to have body I had 5 years ago. As you say, we should give ourselves grace and honor our bodies as they are right now. You’ve shown me it’s possible to be sassy and stylish with class.
Keep up the good work. I really appreciate everything you share with us!
So relatable! Our fall weather made it almost impossible to wear new fall items I had purchased! With temps still in the high 70’s to low 80’s and looking so fall like with all the leaves changing colors! Our normal fall temperatures are just starting ( I think ) I am finding the same issue with tops! I feel like with the jackets I bought a plain white tee or other color goes best! Too warm yet for sweaters unless wearing a chunky one alone! And blouses too dressy unless heading out for dinner etc ! More casual tops are needed and hard when I’m also drawn to a fashion sneakers with the jeans I’m wearing( barrel or wide leg)No heels they aren’t practical for everyday wear ! So I do switch it up with a mule or loafer from time to time just to wear something other than a tee under a jacket !
A more casual day would be straight leg jeans and a comfortable sweatshirt and fashion sneaker! Or wide leg athletic pant!
Wow! How timely! I retired earlier this year and managed to get through the summer with the very casual items I always wore on weekends and a few nicer tops. However, I really want to improve my wardrobe for next summer. I passed on most of the things I wore for work. Now that fall is here, I’m struggling to reconcile my now very casual lifestyle with the more classic styles I’m drawn to. I like to feel put together, not thrown together. Your suggestions have been on point. I’m looking forward to seeing your choices as you navigate the changes life brings us.
Me too!! Agree on shoes/jeans/pants combo as well. I have a limited budget that I am willing to spend and feet that need good shoes, Vionic. Add in I work from home and most of my attire I’m drawn to is leggings/athleisure. This is so helpful that I’m not alone. Thanks for always helping us out and being real.
I love NC! Such a nice drive and beautiful state. Enjoy your weekend getaway.
If you ever are looking for a great fall getaway, I was in Hocking Hills (Ohio) last weekend and the hiking was incredible. Gorges, cliffs, caves. Beautiful state park.. You have all the necessary hiking clothes and shoes! I could have used hiking poles tho.
Hi Jo-Lynne, the description of your situation fits mine, exactly. I have had to go up in jean size recently (menopause!) and since I’m short, I have to get everything hemmed. Like you, the biggest hole in my wardrobe is the elevated tees. It dawned on me a few weeks ago that my biggest struggle is not having enough tops and shoes, especially for this in-between weather, and I discovered that as cute as flats/mary janes are, I’m either a minimalist when it comes to shoes (sandals) or I want my feet completely covered (sneakers/boots). Thanks for this post!
This definitely hits home for me! I’m also struggling a bit with the jeans/shoe combinations. Makes me wonder if I should also shorten some of my jeans, since I usually like to wear flats? A couple of my favorite pairs only work with a heel, and that tends to feel less casual, which is really my lifestyle. I also appreciate the issue about more fitted tops—I’m in my mid-60s & the struggle with weight around my middle is never ending! Thanks for all this great advice & your honest insights!
This post is so relatable. I need tops that are not tight and not too short. I’ve looked at Evereve but haven’t found any.
A resounding “yes” to every issue you mentioned. I’ve been struggling with all of them.
Last night, I pulled things out of my closet and spent a lot of time trying them on in different combinations so that I could pinpoint the holes in my wardrobe. As I started listing all the additional pieces that I thought I would need in order to pull everything together and wear all of it, I realized that not only would it break my budget to buy these things, but that I would also end up with a surplus of outfits that would work for church or going out, but nothing more casual that would suit my day-to-day life.
My favorite fall go-to outfit or “uniform” is jeans, an elevated sweatshirt, and sneakers. In winter, it’s jeans, a sweater, and low-heeled, casual boots. So, I’m going to put those things at the forefront of my mind when I go clothes shopping. I don’t need any more outfits for church or going out, just a couple of shirts or tops that will enable me to wear all my jackets. I have the same challenges you mentioned these particular pieces.
I would love it if you would post an update or sequel to this post to show us how you made your clothes work together and made them work for your life, particularly where it comes to the base layers that work best with different jacket styles.
Thanks for your timely and insightful post!
This is a fabulous idea, Rhonda! I find your transparency navigating these issues so helpful, Jo Lynne!
Love this post!! I’m having the same problems!!! Too long jeans for my day to day shoes and. Needing more casual tops that I actually wear everyday!!
Thanks!!
Great post! My biggest struggle is from summer to Fall and the shoes with pants. I’m not sure it will ever get easier .. lol
Good post, I can relate. Lucky for me, I have not changed sizes so don’t have to worry about that (even through menopause and kids) but living in California where yesterday it poured rain and was 58 degrees and tomorrow it will be in the high 80s with sunshine makes it challenging, we never put away the summer tanks or shorts and being semi-retired, it’s harder to figure out. Lately I’ve been going through some things, and I’ve realized that life is fragile and can change in the blink of an eye, so this year I really implemented shopping with intention, yes that means buying way less and only buying and wearing only what I love and what works for me and if it’s not the latest trend or if wearing patent loafers with jean shorts and a graphic tee makes people give me side eye, oh well, and btw love the Z Supply henley, ordering now!!
Jo-Lynne, thank you for being so real with us! I am in the same boat and appreciate the advice and tips. Can’t wait to see the new says tops you found!
Good morning!
A question for you Saturday Q&A please.
Is it still on trend to roll jeans hems or have one large rolled hem? The length is cropped when done and was popular around here in summer but I’m not noticing it as much any more.
Thanks!
YES!!!!!!!! Thank you for this post and your transparency. Who else is tired of seeing content creators talk about how excellent everything is and how whatever they touch turns to gold? ✋ This post is why I keep reading your content daily. I struggle with the same issues, so I am excited to see what tops you found at Evereve. I also struggle to find the correct shoes to wear with jeans. My 14-year-old asked me if I own any jeans that aren’t “high-waders”. Finding the proper footwear with jeans is easier when it’s warmer out.
I really appreciate your honesty, and from the responses, it looks like a lot of us are going through the same thing. I’m really trying to shop for the life I have, and found great shoe/boot options during the NSale. The Steve Madden boots in black leather and brown suede, and they have a “sister” mule that I got in two colors, plus I got more Maryjane’s, which I love, and I have 3 styles/colors in the Addias Sambas and Specialze style. I recently bought a few plain long sleeve tees at JCrew and a few other stores, and have focused on elevated sweatshirts and tops to go with jeans, which I have been buying at a length that can work with both low heel boots and mules, and my Adidas and mary janes. It’s a work in progress, but I am slowly figuring it out. I loved this post, and look forward to your try ons.
Your blog today was spot on for where I am too!! I am struggling with who I am with clothes, and what works for me, and even what I like anymore! Thank you for making me realize I’m not alone in this struggle! I’ve always enjoyed your blogs, and I always appreciate the work you put into them!
Thanks so much for this honest post! I think it’s one of the most helpful I’ve read. I look forward to seeing your finds of more casual less fitted tops.
I just read about a clothing brand on another blog this morning (Jessica from Side Note) that I have never heard of. It’s called Buck Mason and she was happily surprised by the quality of their Slub Easy Crew t-shirt. Maybe that is the fit you are looking for to wear with jackets. I think I will check them out too!
What a timely post! I spent time yesterday going through all of my clothes (all seasons). “Don’t wear, don’t wear, don’t wear…”. This time I actually bagged them without second guessing. No more “maybe someday,” no more shopping without intention.
I could sense your struggle lately. So many items from your try on hauls never appeared in your “what I wore lately” posts. I understand you have to provide variety for your blog and business, but I love the posts that “feel” like Jolynne!
You often say your everyday outfits can feel redundant or boring, but so are most women’s! I think most women are here for inspiration and your outfit creating ideas and advice. And no one else comes close to your honesty and sense of humor!
Thank you sooooo much for this!
Once again I appreciate your honesty and being “real” about struggles. I too have been struggling and trying to identify my wardrobe needs. Shoes and tops are my trouble areas. These points you offer are so helpful. AND your encouragement for extending grace is perfect! Thank you…thank you! Warm weather here in the midwest has also made fall dressing a challenge for me. Once the cooler temps arrive I am ready with an abundance of sweaters for the season and beyond into winter! Thanks for your post!
Boy could I relate to this post in every way. Thank you, thank you for being real for the challenges we can face when getting dressed and for the body struggles we also can have as woman and the change of life fluff. I’m glad you are hemming your pants. For me I find wearing a heel these days for my casual life style just isn’t happening. Even my church is casual dress. It’s easy for me as a blog reader of yours, Cyndi and Kay, I can end up ordering something you guys style that’s so cute, but then I have nowhere to wear it or only a few times. Right now I’m loving my jeans…. That fit and Quince crew neck all cotton sweaters. They are heavier weave and since I’m allergic to wool, work great for me. I throw on a cute sneaker, mule or loafer and completer jacket if needed and go. I know it’s harder for you as it’s your job to style many things, for different occasions. I’m looking forward to seeing what you find for casual, elevated tops like from Evereve. I have a bday gift card for there that’s burning a hole in my pocket. lol When I don’t have a gift card I find all kinds of things I want from there. I just ordered some Quince jeans to try so hope they work. I’m finally finding some styles that I feel good in from Kut from the Kloth. Great post today Jo-Lynne. I’m sure we all hear your struggle. You might need to get sick. I got sick for a week and my jeans fit better. lol Enjoy your trip. If you ever find a single breasted trench coat again like your last year one in the light cool time cream please post it. I’m killing myself for not ordering it when you posted it last Spring. The warmer tone ones out now don’t work for my skin and hair greying. Thanks.
Great thought – focusing on what I really need and wear in this season of life. “.. my closet should accurately reflect my current lifestyle”.
Oh and the Jean / shoe combo is unending !😂
Thank you ! That frees me up !
PS Just let me say and remind you that you look great and have been styling clothes great. You are giving us great ideas.
Jo-Lynne……..I second that about outfit making! I use to take pics of the outfits so I wouldn’t forget in a fast hurry but haven’t in along time. Might help me to do that again. I am very petite and some would use the word tiny. I don’t feel tiny as go to weight classes but have a small bone structure which lands me in xxsp or xsp petite section. I lost weight and didn’t mean to but had a million things happen at one time and off it came. Now trying to decide to order 0P or wait and gain weight back then order 2P. I can relate to why my Mom wore dresses as one piece and done but I do love my jeans. I will try and follow your suggestions and advice. Thanks for posting this for us!!!
As part of the Medicare club I’ve avoided thin bodycon styles for awhile especially as gravity & menopause have done their thing – I’m a fan of LL Bean more substantial & flattering tshirts in various colors necklines sleeve lengths 🙂
I’m struggling to find tops to wear under jackets that can stand alone. Found a winner at Macy’s of all places. Cap sleeve, light weight sweater with a slight v neck and back, multiple colors. I bought the toffee, but will probably go back for black and vintage cream. I’ve been wearing the one on repeat, so cute under jackets and alone. Size up if ordering. I usually wear small, but bought medium to get more drape. I.N.C Women’s cap sleeve sweater.
This was a helpful post–I appreciate the relatability and also the lessons you included. I’ll be coming back to this one! Thank you!
This was a great post
Fall is always very hard for me as well. The colors of vibrant and pretty always seem to dreary for me.
At times I feel like I’m wearing the same thing every day and my weight fluctuates as well. On many jeans and pants I’ve gone up a size depending on the maker and having that looser fit makes the top look better. I feel better rather than feeling frustrated that I’ve put on a few pounds every day and making myself unhappy. Until I’m back to my ideal weight and shape. Sometimes I feel like I’m just in the middle of two sizes.
Thank you for being so open about
“ body image” and how we can feel different each day. I’m in my late 40s and realize that tight/form fitting clothes aren’t doing the job…..I don’t feel comfortable. Trying to find my style through clothes has been a struggle, but thank you for being so open and giving practical ideas.
WOWZA!!!
Seems like we are all feeling it!!!
The way the seasons go now. Hot one day Cold the next adds to the frustration
I think we would all like to see some of your solutions
I know I could use more direction
I stuggle too. It’s only the last couple years that getting dressed is so much more difficult for me. I am 51 and have gained some weight around my mid section and all my clothes and/or combinations that I used to wear just don’t work for me anymore. I should work on my denim-shoe combo’s because that is definitely where I am struggling. I pretty much just buy Vionic and Ecco shoes now because they are the only shoes that are comfortable for my feet and that is definitely why I am struggling with the denim-shoe combo. There are no flats out there that looks cute and is comfortable. I need arch support, so if there are any out there, please mention that! My lifestyle has also changed since Covid and I am much more home (and ordering online instead of going downtown). Thank you for this insightful post!
I am in a similar struggle with clothes. Having to build my wardrobe after weight loss and find that some of the styles available now (crewneck tees) I don’t like on me. And when I recently purchased a different size in the Paige denim I purchased a couple years ago, the new ones were thinner and felt cheaper quality which is frustrating! I am streamlining my new wardrobe as it will be easier to maintain and I don’t like how quickly the trends are changing causing us to throwaway perfectly good less trendy clothes.
Paula, so true about changing trends! Even though I don’t go overboard buying trendy items, you can’t deny that a woman’s outfits can look dated without newer pieces/styles. I still like wide leg pants but am over the cropped versions. The one time I saved a bunch of denim (bootcut jeans) for when they made a comeback, I pulled them out and realized they were low waisted and I was no longer “waisted!”
I can only shake my head as I watch my husband get ready – same length pants, simple shoes or sneakers that go with everything. Very frustrating.
Welcome to the Mountains! The leaves are gorgeous this week. 🙂
Your post today speaks directly to me. For the past few years I have really struggled with the trends as well and a lot of times I just choose to opt out. Lately I find myself reaching for more classic pieces in my wardrobe and my casual uniform has become straight or flare jeans, Birkenstock mules or sneakers and a sweater, sweatshirt or tee and jacket. For me having 3-4 set jeans/shoe combos has been helpful. Giving myself permission to just let a trend go by and not feel the need to participate has been very freeing. I will say though I am loving the preppy and tailored looks this fall as they definitely fit my personal style.
Love this post! My problem is that I identify the problem but then cannot find things I like to replace or to fit what I need. Am I just too picky. I love shopping and look at many different shops/stores. I think that would make a great post!
Things that also affect how you dress are illnesses and surgery recovery. Three weeks ago I got shingles on my right lower back and waist area. I had to wear loose clothes preferably dresses. I had nerve pain that is gradually going away . I bought 2 straight maxi t-shirt dresses for church and I have drawstring track pants that are comfortable. Since I feel so much better this week I hope by the end of the month I can wear my regular pants and jeans again. I haven’t even been reading fashion blogs. The title caught my eye.
What an excellent post! I’m right there with you 100%. When I look in my closet at the tops I have, I no longer love the majority of them. And it’s come to my attention that my taste has really changed from last year. I will share any tops I find just in case they might work for you or some of the other ladies. I will admit that it is hard for me to accept my physical changes as I’m one week away from turning 69. I don’t have any place where I can have my jeans hemmed, & I can’t wear heels over 1”, so the longer jeans don’t get a spot in my closet.
Oh, yes! I keep trying to reevaluate my closet for my lifestyle. Most of my days I am in workout clothes, and that’s fine. But when we go out to run errands, maybe to friends’, or appointments, I am struggling. I also have too many bootcut jeans that I cannot wear with flats due to their length. I haven’t gotten to the point of finding a tailor to shorten them. I do love how bootcut jeans look since my long legs are one of my best features. Living in North Carolina means that heavy sweaters are not really necessary. What to wear in the fall that is not wintry?! I don’t want to wear my summer clothes, even though the temps are in the 70’s-80’s, but anything that I have that would work for fall colors – they are too heavy for the temps.
I think I need to take the time to go through my closet, see what I have for outfits, so I know what I need to look for.
Absolutely love and needed this post. Very timely. Thanks!
I wanted to share that I love reading your blog. I feel that many of the influencers I follow are “buy this!buy this” but there’s no context and I start to feel like they arent really interested in “sharing” but “shilling”. Your commentary adds a touch of real to what you post and your opinions are appreciated and valuable. This entry was incredibly eye opening to me as I feel like I fall into the same trap of buying whats current (and influenced) but is it really relevant to my lifestyle. This also comes back to the “quality not quantity” rule. Sure, I have tons of stuff, but is it relevant and realistic to my life? I also love that you are honest about body image, and how things fit and feel. So many times we buy things that do not look they way they are shown on someone’s reel, etc. Thank you for being real.
Thank you for being transparent. I too have issues with the middle section. And as I age, it gets difficult to shed those pounds. I don’t like tops that cling to me at all. I don’t have a transitional wardrobe either. I live in Kentucky and weather is tricky. Thanks for what you do.
This! This! This! I could just hug you all for keeping it real and relatable! Jolynne, THANK YOU for this post. I love every comment here today and it makes me feel so much better to know I’m not struggling alone. The weight, the weather, the styles, jean length, shoes…All of it! I can’t wait to read the sequel to this! Thank you all and you Jolynne for all you do for us. I follow you almost exclusively and have very much the same style aesthetic. We can do this ladies!!
This! This! This! I could just hug you all for keeping it real and relatable! Jolynne, THANK YOU for this post. I love every comment here today and it makes me feel so much better to know I’m not struggling alone. The weight, the weather, the styles, jean length, shoes…All of it! I can’t wait to read the sequel to this! Thank you all and you Jolynne for all you do for us. I follow you almost exclusively and have very much the same style aesthetic. We can do this ladies!!
Thanks, Jolynne, for this timely post. I’m retired and in my 70’s and I have to remind myself that my lifestyle nowadays is very casual. Love your blog. Thanks for the tips and suggestions and for your honesty!
Perfect timing. I thought I was the only one. The shoes, pants or jeans, tops coordinating is challenge for me lately. I looked to you for inspiration, however, my wardrobe is definitely lacking shoe options due to my sensitive feet. I only can wear Vionics or similar, with an orthotic insert. I’m trying to stick to a budget, on,y adding pieces that are classic and fit well that I’ll reach for them. I’m struggling. This came at a perfect time. I decided to purge anything that isn’t comfortable or that I didn’t wear last season, or I just don’t like anymore. I’m getting to the point where I’d rather have a few items I love than a closet full of things that I don’t choose to wear. Thank you for this timely post!!
Enjoy your time in North Carolina. I love that state. It’s so beautiful. We were in Winston Salem and Topsail in September.
If you love fall getaways, I was just in Hocking Hills (Ohio) for the weekend. Beautiful area, the state park is so gorgeous and unexpected with it caverns, caves and cliffs. The hiking was rigorous but you’re all set with your hiking gear.
Have a great safe trip.
Can you make this into a series ? I feel so many of us can relate . Especially tops under jackets . You have amazing arms so this may not be on your radar I need elbow length or I won’t take my jacket off . I feel like this post is going to be your best post of the year . Thank you for being so honest
I can relate to every single issue you write about and look forward to the tops you find that can stand alone and also under a jacket. I have plenty of sleeveless tops that work under a jacket but only if I do not plan to ever remove the jacket….and nothing is ever for sure!
I stopped in Evereve last Sunday and picked up a few things – a favorite daughter sweatshirt and a henley and a flannel to wear over the henley. I work from home 100% of the time and, too, tend to wear jeans and elevated basic tops and sweaters and fashion sneakers. Plus, two broken feet in the last 8 months means that any type of heel is out for the foreseeable future. I can’t wait to see what you picked at Evereve.
Thank you for this!! I was just planning to go over to someone’s house for coffee today and wanted to wear one of my lightweight jackets that I love and was struggling with what top to wear in case I took off the jacket, which I likely would!…Annnnd I just had to put a pair of corduroys in the donate pile this morning…because perimenopause did something to me… Thanks for understanding!!
I just lamented to my husband how the challenges of being a woman are never ending. The shoe/jean combination is a complete struggle. Fashion is moving so fast these days, and nothing hurts more than switching over to new denim styles only to realize that 6 months later, they no longer fit due to menopause. It is a real struggle mentally and in getting ready every day. When your body starts to not even feel like your own, putting on clothes that work in real life and that fit well becomes a fashion priority. Keep sharing those real life outfits. I love them!
The whole part about aligning your wardrobe with your real life – lol, I feel like you said that specifically for me. Most of my clothing is for work (think: business casual, but no jeans), I have very little leisure wear. I started to think I needed to get some… like all those cute cozy matching sets, athleisure, jeans, etc, until I realized I wouldn’t get much use out of any of it except on Saturdays. 😉 Anyhow, my other weakness: I *love* cocktail and formal dresses. But I have absolutely nowhere to go. I’d buy them all, but they’d just collect dust. I guess that would be my “aspirational shopping” faux pas. ROFL!!!!! Anyhow, thanks for your transparency!
I appreciate your transparency and that you are giving yourself some grace. I see that the cropped length for jackets is not flattering for my figure. I carry all my weight in the abdomen and can easily look more streamlined with a longer jacket or cardigan. Your words about finding pieces that work were encouraging. Thank you!
Ha! This has been my life as a petite SAHM. I love clothes, but I have few places to wear them. The styles & trends change so much, that by the time I find that cute item that actually fits me, it’s no longer “current”. Our weather doesn’t help. I wear jeans because it’s cold in the places I go, not because it’s remotely cool outside. My goal these days is to add a few new pieces & shoes to look put together. Thanks for sharing your challenges. It’s reassuring to know that I’m not the only one having issues finding good fitting clothes.
I appreciate your honesty! Menopause is not my friend either.
Hey there and happy fall get-away for you! I just read your post above and you make some great points; “focus on fit” is so important to me as is “align your wardrobe with real life.” After retired last year I found myself still shopping for clothes that I wore to work or work events and ended up returning 90% or sadly keeping it with tags on and missing the return window! It took me the better part of this past year to change. I first did a massive closet clean-out trying on everything in it (took me a week), then I categorized and color coded my closet as well as better shoe organization; all this helped me to really see what I had to and where I wanted to add.
Now when I go shopping either in-person or online, I’m getting better at the 3 question rule:
1.) How often will I wear this & what weekly activities does it go with?
2.) Does it fit me well or will I be pulling, tugging, sucking in the middle 🙂 ?
3.) Does it feel good on me and do I feel pretty/confident/happy/comfortable when putting it on?
*One thing I do every fall is stock up on long sleeved tees in a few colors to wear under jackets, blazers, or cardigans. I like the current ribbed one from Michael Stars and I always size up so it’s not clingy.
The one thing you mentioned that doesn’t resonate with me is the jean & shoe combination. I don’t feel a struggle with that one. Maybe it’s location – year round I am able to wear sandals, ballet flats, mary janes, and fashion sneakers with my jeans and pants.
I think everyone hits a wall with fashion at some point and going through menopause changes our bodies more than we realize. It does make it tougher to get dressed at times. I would guess that being a fashion blogger might add a little extra pressure to always dress a certain way and/or keep up with wll the latest trends. Thanks for sharing your real self with all of us.
Thank you for your insightful and helpful comment. I love the 3 questions you ask yourself. I work from home 99.9% of the year and had to rethink my purchases. I live in athleisure most days and find it comfortable. Thanks for sharing. All of these comments have been helpful.
So glad to know I’m in good company! Great post – needed that.
WOW!!! This post was an answer to my prayers!! I have been struggling with all of the things you talked about in today’s post. I have been very frustrated with my clothes lately. I love your blog, and I am feeling encouraged to figure out how to enjoy getting dressed again. Thank you!
Enjoy Blowing Rock!! It is such a beautiful town. I went to college at Appalachian State University. I will be in Boone this weekend for homecoming (my son is a current student). I hope you get a chance to visit Boone and walk along King Street. Try to avoid the crowd on Saturday. You may like a clothing store called Monkees Boutique in BR. Have fun! The weather should be perfect.
I too am struggling with my wardrobe because I buy things that I feel I can only wear in certain settings. Like cute pants to wear to a winery but I work remote so I don’t wear cute clothes to work anymore. I have decided that means I need to do more things outside the house, some activities which will involve dressing up, but also I have decided I don’t care if I’m dressier than others around me. Since COVID I have just wanted to wear real clothes and heels again. So that was my mindset adjustment: wear cute stuff as much as possible where you think you can get away with it. And interestingly, I sometimes see other women doing the same and I feel like we’re in solidarity!
Enjoy Blowing Rock!! It is such a beautiful little town. The weather should be wonderful this weekend. I went to college at Appalachian State University. I will be in Boone this weekend for homecoming. My youngest son is a student there. I hope you get a chance to visit Boone and walk along King Street. Boone will be very busy on Saturday due to the game. If you get a chance visit a boutique called Monkees in BR. I think you might like it. I hope you have a fun trip!
OMG what a great post. I think I’m struggling because hot weather in the midwest went on far too long! Now, I’m about ready to go on my little gf fall getaway trip and figuring out clothes seems impossible–let alone shoes. I went to 3 stores today and came home with only tank!?! Your post is eye-opening and I appreciate it! I need to re-access some full outfits–go to type outfits–like you did. Thank you for the info on the waterproof brooks–guess its not what I was looking for. I look forward to you finding some tops to share with us. My lifestyle is more casual too now and I need ideas!
THESE are the tips I needed to be reminded of right NOW! Thank you.
This post resonated very much with me. I just got back from a girls trip to France that was so much fun. It would have been so easy to buy many beautiful pieces of clothing that we saw but I had to keep asking myself “where will I wear this in my rural Tennessee life?” So I ended up with some colored jeans, a sweater and a blouse that I can wear for 3 seasons. I also feel like this stage of my life is very hard to dress. I don’t want to look like my young adult daughter and although I’m 60, I’m not ready for the matronly polyester look either. So thank you for sharing your struggles and insight. It’s nice to know we are all in this together.
I agree, tops have been tricky this season! And by season, I mean the in-between season of late summer heat to early fall! There are lots of dressier tops and blouses and very few elevated basics it seems. Also, many tops seem ‘micro’ or oversized, off the shoulder and shapeless. You’re not alone, a lot of us are in the same boat! Please post what you do find because you are the professional shopper and I am most certainly not!
Excellent post by the way, regarding correct pant length and shoe selection. I think that’s where we can instantly look frumpy if our pants are too long for ours shoes.
Have a great day!
Great and timely post! I agree with everything that all the other ladies have mentioned 100%. I’m not on social media for various reasons, but I think this community of women that you’ve built are really special and a testament to your character and the way you communicate and live your life.
The issue of what tops to wear under jackets has always been a struggle. I hate it when the jacket neck line and the top neckline and the jewelry all compete.
There no longer seem to be “rules” in fashion the way we used to think of them. “No white after labor day” or “look in the mirror and take off one accessory before you leave the house.” You regularly talk through your decision making process in your try on hauls, and I often think to myself that you should expand on that and make it into a blog post. I wonder if you might do a blog post on general truths (certain pairings complement each other best) and reasons why you might choose to disregard those in favor of a different choice. I’m not even sure what I mean for you to write about! 🙂 Perhaps something like this…we often look better with a v neck because it elongates the line of the neck but a particular jacket might look better with a crew neck top. Hope you have a lovely weekend and thanks again for all you do!
I knew I couldn’t be the only one struggling with trendy tops these days! What a great post — and reminder to give ourselves grace. I changed careers three years ago and have been rebuilding my wardrobe ever since, not to mention perimenopause and all that entails. Man, does getting dressed get frustrating at times.
Like everyone else, I needed this post. The middle “fluff”, being honest that I never want to wear heels again for everyday life, jeans too long, shirts too tight, all of it! Thank you for being honest and keeping it real. I feel like all I own is work clothes or clothes for errands on weekends. Heaven help me if I need something for going out to dinner, or to an event! Even if I might own a dress or two for fancier events, will they still fit when I pull it out of the closet?! Ugh!
In the same boat – thank you for your suggestions!
I feel this ! I work in a church office we are casual but put together finding footwear and tops that go with my pants is hard. I also have finicky feet. I ended where sneakers alot. I wish these looks were a little more pulled together sometime. I am one state over from you in Delware. Where it’s pretty chilly when i leave the house and warmer when i get home. so that is a whole issue. All this to say I am gonna reevaluate what have add on what else would work. you outfits always give me inspiration.
Very relatable article!
Which pants are you wearing in the very first picture? It’s the black pants with the black top
It’s these – https://shopstyle.it/l/cvJMW
I am so thankful for this post. And that I wasn’t able to read it until today. (Life is lifeing over here) Yesterday was my 3 month post op date and I’m terrified that the upper portion of my tummy tuck has failed. Nothing fits. Literally NOTHING. My old clothes are too tight, and anything bigger is too loose. So reading this was exactly what I needed.
I can 100% relate to this honest and wise advice. I love the idea of making your wardrobe fit your actual life (not your ideal version). Thanks so much for being vulnerable and explaining the process. It really helps!
I too have gained 5 to 7 lbs from vacation and getting hooked on Nutella. I keep it for my grands but hadn’t ate it myself. Until I did. I honestly think there is something in it that makes you crave it. Trying to break this bad habit.
Throw it away!!!! 🗑️😜
I loved this post (sorry for the late reply). As a petite lady (0-2P), I really struggle with basic tops & completer pieces. I started with the Charley kick-out crop pants in khaki, black & denim from J Crew. Then I found a coated denim jacket in brown in XS that fit from Kut from the Kloth as well as a cropped barn jacket in leopard print in XXS from J Crew. Now I need basic tops that pair with those pieces. I’m struggling to find tops that don’t swallow my petite frame. Any suggestions would be welcomed. I look forward to reading your post daily.
Thanks
Kathy
Thank you for this post. It was helpful. I appreciate your honesty. I’ve struggled too. Our lives & activities change & it’s easy to get stuck buying clothes we used to need & have a lot of nice clothes but nothing to wear. Things are so much more casual even for many of the same activities.
I’m behind in reading my emails but this post was just what I needed! I find myself struggling with outfits. I seem to be missing the one link to a great outfit- the right shoe, the layering piece under the jacket and even the right accessories. Then get messed up when I see the trends or the article that says a piece is now dated. Thank you for helping all of us!!
Same, girl. Same. I do this for a JOB and I am still struggling. It makes packing for trips a real challenge.
Thank you JLS for the great post! I just took three pairs of jeans to be hemmed, and bought one pair of boots with 3” heels that don’t look 3”. Also, thanks to all of you who commented, I read all and it helped me with ideas and state of mind!😊