And just like that, it’s Wednesday again! That means it’s time for another edition of What I Wore Lately, where I round up my recent everyday outfits and share a little about where I wore them and how they came together.
I’ve done some traveling and had a few celebrations to attend, but I’ve also spent plenty of low-key days at home, so this post is a mix of casual looks and a few dressier moments—basically, what real life looks like this time of year.
Disclaimer: As always, some of the items I’m wearing have been in my closet for a while, so if something is no longer available, I’ll link similar options when possible. I also tried to include a few “similar for less” alternatives for the pricier pieces. Most of these links are affiliate links, which means I may earn a small commission at no additional cost to you.
Two Weeks of Everyday Outfits
Kicking things off with this activewear look I wore to Pilates a couple of weeks ago, my new Vuori matching set in Raisin.
Vuori Canyon Jacket (S) // Vuori Energy Tank (M) Vuori Clean Elevation Leggings (L) // On Cloud Sneakers (9)
After that, I changed into jeans and a sweatshirt to work from home for the rest of the day. I had just gotten the Birkenstock Boston Rivet Clogs, and I was excited to start wearing them. I paired them with an old pair of blue jeans and topped it off with this cozy henley-neck sweatshirt.
EVEREVE Rowan Henley Sweatshirt (M) // MOTHER Dazzler (29) // Birkentock Rivets Clogs (39)
The next day, I had a V-Beam laser treatment, and otherwise, I was just at home, so I wore this casual activewear look.
Z Supply Elin (M) //old lululemon cardigan // Athleta Brooklyn Cargo (6) // Birkentock Rivets Clogs (39)
Another night that week, I met a friend for dinner. I pulled out my Frank & Eileen Trouser Jeans and paired them with my new Mary Janes in chocolate brown haircalf—I think these are so fun for fall! I topped it off with this rose-colored boiled wool cardigan from last season and added a mixed-stone necklace for some extra polish, plus gold hoops.
Vince boiled cashmere cardigan (S) // Frank & Eileen West Village NYC Wide-Leg Trouser (29) (budget option) // Madewell The Remy Mary Jane Flat
in Chocolate Raisin (8) // old mixed stone necklace // Jenny Bird Aurelia Hoops
And then, a casual everyday look from another day that week. This time I paired the Rowan Henley Sweatshirt with my PAIGE Anessa wide-leg jeans and Gola Torpedo sneakers in a coordinating shade.
EVEREVE Rowan Henley Sweatshirt (M) // Paige Anessa (29) // Gola Torpedo (8.5) // Jenny Bird Small Tome Hoops
I had a hair appointment the next day, and I kept it cozy with another activewear look. I think I wore this for a walk earlier that morning, too.
Vuori Canyon Jacket (S) // Athleta Momentum Seamless Top (M) // old Athleta bootcut sweatpants // Brooks Ghost (9) // Jenny Bird Small Tome Hoops // Goyard tote (option)
Then that night, we had tickets to see The Hooters in concert. For those unfamiliar, they’re a Philly-based ’80s rock band, and Paul and I are big fans. They’re definitely getting older, but they still put on a great show! I wore a simple black v-neck sweater with grey jeans and black boots, and topped it off with my AllSaints leather jacket. It was an #NSale purchase, so I found a similar option for less at Mango.
AllSaints Ryder Leather Jacket (S) (budget option) // Jenni Kayne Flynn (S) (budget option) // MOTHER Weekend (option) (29) // Dolce Vita Vaydin (8.5) // rag & bone belt
We celebrated a good friend’s 50th birthday last weekend, and it was a casual outdoor gathering. I wanted to be warm but still look put-together, so I tried on a few outfits, but nothing was quite coming together. It was partly because a lot of my jeans were feeling uncomfortably tight, and my newer ones were at the tailor getting hemmed. Plus, I really wanted to wear sneakers, which limited my choices even further.
I started with this combo, thinking the barn jacket would be the perfect topper for a fall outdoor event… but when I came downstairs, my husband said something looked off, which confirmed my suspicions.
Gap Factory Barn Jacket (S) // Gap Factory Stripe Sweater (S) // PAIGE Anessa Raw Hem Wide Leg Jeans in Mesmerize (29) // adidas Spezial (8) // Clare V Midi Sac // Jenny Bird Florence Earrings
He didn’t seem to like the denim/shoe combo, so I started by swapping out the raw-hem jeans for a finished-hem pair, but they’re a smidge longer, which meant I needed to change into boots. I thought maybe the heel and the more polished jeans would make me feel a little more pulled together, but I still didn’t love it.
I went back downstairs, and both my husband and daughter weighed in. We determined it was something about the sweater with that big brown hem, paired with the boxy jacket and wide-leg jeans—they were all competing with each other, and I think there was just too much volume on top and bottom. Plus, I really wanted to wear sneakers. It just made more sense for the event, and I knew I’d be on my feet for hours.
Gap Factory Relaxed Canvas Barn Jacket (S) // Gap Factory Stripe Sweater (S) // PAIGE Anessa High Waist Wide Leg Jeans in Dresden (30) // Dolce Vita H20 Booties (8) // Clare V Midi Sac // Jenny Bird Florence Earrings
By that point, I was getting pretty frustrated. Even Paul was like, What is going on? After so many years of putting outfits together for my job, I can usually pull something together fairly easily—or with just a few simple swaps. I mean, I certainly have enough clothes to choose from! But I was starting to feel overwhelmed by the pressure to “get it right” because this is what I do… and I know that’s silly.
Anyway, back upstairs I went. This time, I decided to grab pieces I’ve worn together before and know I like.
I went back to the first pair of jeans and grabbed my old faithful Jenni Kayne Flynn sweater and the cropped barn jacket, but it felt too dressy for sneakers. So I added these brown flats and a belt. I threw it all on and went downstairs before I could second-guess it.
I didn’t even stop take a mirror selfie, so I asked Paul to take this photo outside by the pumpkins, and when I looked at it to make sure he’d captured a pose I was okay with, I was like, Nope!
Avery Barn Jacket (S) // Jenni Kayne Flynn in Oatmeal (S) // PAIGE Anessa Raw Hem Wide Leg Jeans in Mesmerize (29) // Jeffrey Campbell Fathom Flat (8.5) // Nili Lotan belt (M) // Jenny Bird Florence Earrings // Davina Stone Necklace
The color of the shoes throws everything off, and it’s such a strange mix of dressy and casual. Plus, the proportions were all wrong. The jacket feels too rugged, the frayed hem too casual, and the beaded necklace and alligator-embossed belt too fussy. I think this was my least favorite combo yet. You should have seen Paul’s face when I went back upstairs… I’m giggling just thinking about it.
This time, I was like, Forget it. I’m just wearing the old stuff that I know works. I grabbed the adidas Spezial sneakers and my old MOTHER Dazzler slim straight ankle jeans (even though they feel a bit dated, at least they work with the sneakers), kept the Jenni Kayne Flynn sweater, but left it untucked to keep things simple and unfussy. Then I made a split-second decision and reached for my green Barbour quilted jacket, even though I was getting tired of it. It’s just so good for an elevated-casual fall look.
It’s not as cropped as the Avery Barn Jacket and not as boxy as the Gap Factory Relaxed Canvas Barn Jacket, plus it’s a bit warmer than both, which was nice because it was a chilly day. It’s also long enough that I could leave the sweater untucked, which felt so much less fussy and eliminated the belt issue. (I’ve since purchased a more casual dark brown belt!)
Barbour Jacket (6) (option) // Jenni Kayne Flynn in Oatmeal (S) // MOTHER Dazzler (29) // adidas Spezial (8) // Jenny Bird Florence Earrings // Davina Stone Necklace // Clare V Midi Sac
I didn’t exactly love this look either, but at least it felt appropriate for the event and the season, and everything worked together well enough. I had a great time, and while it isn’t the most modern outfit I could have worn, I didn’t feel too fussy or too frumpy—which I think I would have with any of the other options I tried.
Believe it or not, the very next day I had to pack a suitcase and fly to Nashville! While I was trying on outfits for the birthday celebration, I was also thinking ahead to what to pack for this trip—which, in retrospect, probably added to the overwhelm.
I knew it was going to be rainy, so my new Bernardo raincoat was a must. For my travel day look, I went back to some of my dependable wardrobe staples.
As an “influencer,” I always feel the pressure to wear new and different things. But when I’m struggling to put outfits together, and the current styles feel foreign and half my clothes don’t fit, all I know to do is go back to basics. This is when I’m especially glad I invest in quality basics. Even if they aren’t on the cutting edge of fashion, they still look polished and put-together.
I wore the Jenni Kayne Flynn sweater, dark wash flares, and Veronica Beard leather booties. Everything else I wanted to bring fit perfectly in my AWAY Bigger Carry-On Flex.
Bernardo Rraincoat (S) // Jenni Kayne Flynn (S) // MOTHER Weekend (30) (budget option) // similar boots in Espresso Leather (8.5) // Davina Stone Necklace // Tom Ford sunnies (option) // Goyard tote (option) // AWAY The Bigger Carry-On Flex
That night, I changed into this top to go down to dinner at our hotel. This was the only picture I managed to get. Our room was pretty tight!
Colette Cardigan Top (M) // MOTHER Weekend (30) (budget option) // similar boots in Espresso Leather (8.5) // beaded necklace // similar link necklace // Jenny Bird Florence Earrings // Clare V Moyen Mesenger
The next day, Cyndi and I met our friend Lisa for lunch. It was a dreary day, so I kept it casual in my black J.Crew cardigan and black jeans, paired with Mary Jane flats. I love the double straps and narrow vamp, for a more updated look.
J.Crew Cardigan (S) // MOTHER Dazzler (30) // Baylee Leather Mary Janes (8.5) // Anna Beck necklace // Florence Earrings // Clare V Moyen Mesenger
That night, Cyndi and I had tickets to a concert at the Ryman, so I changed into dark wash flares, a black cowl-neck top, and my AllSaints leather jacket in Oxblood. I love the stand collar and boxy cropped fit.
AllSaints Ryder Leather Jacket (S) (budget option) // Vince Cowl Neck (S) // MOTHER Weekend (30) (budget option) // similar Veronica Beard boots (8.5) // rag & bone belt // Freja Hudson Bag
The next day, I moved to a hotel closer to Belmont, where my daughter goes to college, so I could spend some time with her. I wore this cardigan top again—this time with my black jeans and the black Mary Janes. I just kept the same outfit on when we went out to dinner.
Collete Cardigan Top (M) // MOTHER Dazzler (30) // Dolce Vita Baylee Mary Janes (8.5) // Florence Earrings // Anna Beck necklace
Before I knew it, it was time to head home! I didn’t feel like wearing the boots and flares again, so I managed to fit them into my suitcase and wore the Mary Janes, black jeans, and black cardigan instead.
J.Crew cardigan (S) // MOTHER Dazzler (30) // Dolce Vita Baylee Mary Janes (8.5) // Florence Earrings // Anna Beck necklace // Goyard tote (similar) // AWAY The Bigger Carryon Flex
Back at home the next day, I decided to take my new Birkenstock Boston Rivet Clogs for a spin. I threw them on with these old blue jeans and a sweatshirt cardigan. It’s a little low-cut, so I layer a brown ribbed tank underneath.
Corinne Sleek Sweatshirt (M) // Z Supply tank (M) // MOTHER Dazzler (29) // Birkenstock Boston Rivets Clog (39) // Jenny Bird Tome Hoops
I had a mani/pedi appointment on Halloween, and it was a chilly, windy day. I pulled out this cozy cashmere sweater and paired it with slim bootcut jeans that roll up easily in the pedicure chair. These gold flip-flops have great support, which I love.
White + Warren Striped Crewneck (M) (similar) (budget option) // MOTHER Insider Flood (31) // FitFlops (8) // Jenny Bird Tome Hoops
Paul wanted to go out for dinner that night, so we left our daughter to man the door for our trick-or-treaters. I wasn’t in the mood to change, and it was still chilly, so I just swapped the flip-flops for boots and threw on my Barbour quilted jacket.
Barbour jacket (6) // White + Warren Striped Crewneck (M) (similar) (budget option) // MOTHER Insider Flood (31) // Aquatalia boots (9) (budget option) // Jenny Bird Aurelia Hoops
I met a friend for lunch and shopping last Saturday, and I had just done some try-ons and found this Amazon jacket. It’s a dupe for the viral Zara one I tried on (and left) at the store in London—which I have since ordered in brown to compare. I couldn’t resist giving it another try!
And these are the AG Brinley jeans I found when I was shopping with Cyndi at the EVEREVE in Franklin, Tennessee. I originally wanted them to wear with sneakers, clogs, and other flat shoes, but they actually work with boots too!
faux suede bomber bubble jacket (S) (Zara version) // LNA tee (M) // AG Brinley (29) (budget option) // similar belt // Dolce Vita H20 (8.5) // Clare V. Moyen Messenger // Jenny Bird Aurelia Hoops // Baublebar link necklace
Side note: I don’t love this belt with the outfit. Since there wasn’t any light brown anywhere else, the lighter belt looked a bit off—but my dark brown one felt too dressy, so I just went with it. I ended up purchasing a more casual dark brown belt while I was at the mall so I’d have that option going forward.
You don’t have to match your belt to your shoes, but I do like the effect. A printed belt would work too—I actually love the idea of a cow-print belt here, especially one with deeper brown tones.
For church on Sunday, I pulled out another piece I found at EVEREVE—this plaid wool jacket with the faux leather collar. I paired it with the faded black MOTHER Rollers I just got back from the tailor. Now they’re the perfect length to wear with my lower-heeled boots!
For top options, I could’ve gone with a light neutral to pull from the tones in the jacket, but I decided to go with a black top instead. I almost wore this scoop-neck tee to open up the chest area a bit, and I do think that would look better than the crewneck sweater. This feels pretty “buttoned up,” but it was a cold day, so I kept it.
Dakota Plaid Wool Jacket (S) // Vince cashmere sweater (M) (budget options here and here) // MOTHER Roller (30) (budget option) // Vince Sutter Booties (budget option) // earrings // Anna Beck necklace // Hudson bag
Monday was an “admin day,” so I stayed home and caught up on computer work and returns. I wanted to try the AG jeans with my Birks, since that was really the purpose of the purchase, and I love how they work together. These jeans are so soft and stretchy they practically feel like pajamas! I topped it off with a cashmere hoodie to keep things cozy and casual, but still a little polished.
Nordstrom cashmere hoodie (S) // AG Brinley (29) (budget option) // Birk Boston Rivet (39)
I wasn’t planning to wear the same jeans two days in a row, but I wanted to wear sneakers to Bible Study yesterday, so it just worked out that way! This black and white striped sweater is one I’ve been talking about a lot, so I was happy to finally get a chance to wear it. My initial instinct was to pair it with black jeans, but I decided to go with blue instead to keep the look more casual.
Caslon stripe sweater (S) // AG Brinley (29) (budget option) // VEJA Campo
These sneakers are the VEJA Campo. My VEJA Esplar in the black/white are looking really worn, so I decided to update them with this pair. I like how they’re a little chunkier—almost a platform—and they’re super comfortable, too.
I topped everything off with a black faux leather puffer vest from last year and added a belt and a front tuck to create a little point of interest and define the waist.
Caslon stripe sweater (S) // similar faux leather puffer vest (S) // AG Brinley (29) (budget option) // VEJA Campo (39) // rag & bone belt (M) // shield earrings
And that’s a wrap on the past two weeks of outfits! I hope it gives you a little inspiration for your own everyday looks. Let me know if you had a favorite, or if you’ve been struggling with outfit ruts too. I always love hearing from you!
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24 Responses
Love all of your outfits! Thank you for sharing your dressing dilemmas-I face these issues here lol and sometimes just go with it! Do you think Evereve will run a another sale soon getting closer to Black Friday? Dumb question, I know, just can’t recall timing from last year?! I missed the last sale you mentioned due to work and visiting our son in Austin. I really love the Rowan Henley and Collette Cardigan–I am guessing these would be quality tops that could be worn for several years….trying to be a mindful shopper!
Your church outfit is FIRE 🔥, as the kids say. Thank you for taking us through your pre party try ons. The struggle is real with wider legged jeans and wanting to wear sneakers for comfort. Even though some slimmer legged jeans are not trending, they are more flattering on most of us and soooo much easier to style with sneakers.
I SO get the party delimna — this past Sat I added a bar to my closet to allow my jeans to spread out a bit and let me tell you that totally threw me into a spiral on Sunday while trying to wear something I hadn’t worn before (because I could actually see all my choices now) I think I threw on 3 or 4 different pairs of jeans before settling on a pair of black old navy cropped pants, go figure so I feel your pain we just have those moments at times.
Trudging up and down the stairs for a family fashion vote. Crack me up! Sometimes things seem off and we can’t nail down the reason. Try, try again. 😂
Definitely relatable.
I had list your post for a while now that i found it again I noticed something different about it have you changed web designers
Church outfit and outfit following with white hoodie are the best. Sometimes when getting ready to go to a function, my closet looks like it exploded…then when I get home I have to deal with the aftermath.
Thank you for sharing your pre party attempts at an outfit. It helps to see the process and the reasoning behind what works with what. I am currently struggling with what tops to wear with high waisted wide leg jeans (like the Paige Anessa or the Mother Roller etc). I can’t seem to get the proportions right, tucking in is tricky for me being short waisted coupled with the age-related mid section fluff!
Michelle, both of those jeans are pretty high waisted. I always get confused between short waisted bodies and long 🤪. But! That may be the reason finding tops to pair with them is a struggle? Perhaps a lower rise would be better for you? It’d be fun to have you try a mid rise and circle back with us if you saw a difference!
I don’t think that you have to have so many new outfits to share with us. Realistically, most of us have a limited clothing budget so we have to wear the same outfit over and over. Just because you are an influencer, it doesn’t mean that your clothing budget is huge. I actually like to see you that you have some of your favorite outfits on repeat.
I am sorry the birthday party outfit was such a dilemma and I might have laughed out loud at the family vote and the number of times up and down the stairs! Yes, we can allll relate to that!
I love the variety of Mary Janes that you have and I appreciate that you explain how to style them.
Have a great day!
Sometimes it’s less about “staying current & modern” & more about what looks good on us & we feel good in. I feel like the slim-straight jeans are so flattering on you! The wider pants & flares look so heavy to me, & they tend to add visual pounds (not something I need!) I got a chuckle out of all the outfits you tried! Thanks for keeping it real!
First I really didn’t think the outfits you didn’t like didn’t work for the bday. I just didn’t care for the cognac ballet flats with the one outfit but other than that I think it was a menopause brain fog, nothing fits day. Lol It really changes my mood and decision making. I’m going through full blown menopause at 64 yrs old from being on hormones all these years after hysterectomy. It’s crazy land for me now. Still weining off hormones. Sooooo, I also think because of your job you put lots of pressure on yourself to get it right. I’m so glad so many denim styles are in right now as once skinnies left it’s harder to dress for sure. I’m constantly trying to figure out the right denim boot or sneaker or loafer etc combo. I find myself too often putting the same combo together and going. I think also if we have a more casual life style it’s harder to wear all the other things in the closet. It can feel too fussy as you say. Sooo, I think you did great the last two weeks. Looking forward to more late Fall and Winter outfits to come.
I love your church outfit!
My favorites are the Vuori matching workout set and your bible study outfit with the striped sweater, black vest, AG Brinley jeans and Vejas (super cute!). I love the raisin color; Ahtleta has that colorway also and I think I’m going to purhase the leggings and jacket. (How can I find your Athleta shop link?)
I also have to say that I prefer the Jenni Kayne ivory sweater paired with the Barbour jacket instead of the brown striped sweater. I know you love chocolate brown and it’s everywhere now, but I feel like when I see you in bright primary colors your face just glows! I bet that Barbour jacket would be cute paired with burgundy or a wine colored sweater as well as navy or even a darker shade of green. Just a thought.
****Sorry to be a “Negative Nelly” but the pop-up ads have been really intrusive lately. This morning I had to close out your blog post twice on my phone and then came to my laptop to read it instead becasue the pop-ups are easier to navigate around on this device. (I know ads are important to your business, but thought I’d share since it’s been harder to read your content.)
This is fantastic!! I had a day recently where I had quite a few things on my bed laying out that weren’t quite working for what I was trying to formulate for an outfit!! I was thinking to myself, “I bet Jo-Lynn doesn’t struggle with this, ha ha”. Thank you for keeping your styling life along with everything else real. Love these suggestions. I definitely am a casual dresser and appreciate the ideas. You’re the best.
Also, I’m not sure when you gave us the suggestion for the Target candlesticks and remote candles, but I purchased them and love how they look!! Even my husband said how nice they are. I’ve been thinking about gifting a set to a few people I know! Thank you.
While I am not documenting my daily outfits for the public, I understand wanting to look current.
Imagining it, I would have thought the Adidas, combined with the V-neck sweater and casual jacket, was a good combination, if not for the dressy belt. I am all for wearing belts but sometimes they’re too much. I like your idea of adding a cow-print belt to the mix, great for bringing light and dark together in an outfit or keeping accessories from being too matchy-matchy.
Well, it’s good to know the struggle is real. I said to my daughter the other day when we wore skinny‘s or even just the straight style of jeans, it seemed a lot easier to get dressed , now there’s so many different style jeans. We’ve got the barrel jeans, the wide leg jeans, the crop jeans, the flare jeans , the crop flare, kick cropped, and so on and with each of those different styles of jeans, there seems to be certain styles of shoes that are needed …certain styles of tops and also jackets which leads me to the upcoming season of winter. If we are wearing our barrel jeans or wide leg jeans and we’re wearing a high shaft boot that goes underneath of them.. if they happen to still be a bit cropped or on the shorter side What jacket are we to wear? I feel like the longer puffer coats even that cover the bum are going to be too long for that style of Jean. Are we to wear cropped jackets ?
Not sure if this is something you can address with your questions on Saturday, but if you could show some coat options for the barrel jeans and the wide leg jeans that would be great!
The coat question-that’s what I am wondering. Would love to see examples.
I’ll add it to the Saturday Q&A!
LOL–that’ll be the day my husband critiques what I finally decide to wear to an occasion–he knows better! ha ha ha
And I know I’m not alone– of us women who finally decide on something to wear and then later have to come home afterwards and put away all the other frickin possibilities strewn across the bed! Too funny! I think that straight and/or slim flare jeans are still and probably always will be–the most flattering for most of us. Think Jennifer Aniston–she never gave into the barrel or wide leg and continues to look current and great. I did give into a couple of wide legs–one of them is that drawstring style–but they are rarely worn. I like the cashmere ivory hoodie you wore, but sadly some of these prices are just too high. The Barbour green jacket is very cute–I’m always drawn to green jackets. But thats sold out–which is probably a good thing! lol
I like the plaid jacket. The outfit looks good on you. I can relate to feeling you have nothing to wear with a closet full of clothes. The link to the Mary Jane shoes wouldn’t work for me. I agree with one of your readers who said sometimes it’s about what looks good on us and how we feel in it not what’s current.
I get the party outfit dilemma! My husband always questions how I can possibly struggle with what to wear considering the sheer amount of clothes I own. Happy to hear I’m not alone! My question I’d about the tailoring of the Mother Rollers. Did you keep the original hem or go with a regular hem?
I kept the original hem. I always do! 🙂
Jo-Lynne, I love your style, and THANK YOU for sharing the struggles, too!! I like what you landed on and would not have been critical of your other options, but your explanation of what wasn’t working is super helpful.
Great outfits! Thank you for your work!!