Fall/Winter Fashion
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What I Wore Lately Vol. 30

Happy hump day, friends! It’s another Wednesday already, and that means time for What I Wore Lately.

This is a roundup of my everyday outfits from the past week. Also, don’t miss my first Gift Guide of the season, which went live this morning!

I’ve got a few “outfit evolutions” in this post. It seems like with each change of seasons, I have to figure out what pants and shoes work together all over again.

Spoiler alert: I think I ended up wearing sneakers every day but one.

What I Wore Lately: Easy Everyday Outfits

SIZING NOTES: I’m 5’5″ and 135 pounds-ish, with a slight hourglass shape. Unless I say otherwise, I’m wearing a 6/28 in pants/jeans, a small in tops, a 6 in dresses/jumpsuits, and size 8 shoe.

Starting with last Wednesday, I had a photo shoot with Alison in the morning, and then I threw on this casual cashmere hoodie and jeans to work in my office for the rest of the day.

This navy hoodie is from last year’s #NSale. I was excited to break it out again, and even more excited when I found it still available at Nordstrom Rack! (I’m wearing my true size small.)

I love the juxtaposition of the luxe knit and sporty hood — it’s more elevated than a traditional hoodie but has the same cool-casual vibe.

I paired it with light wash blue jeans for some contrast. My jeans are an older style, but this pair of Paige Hoxton crops has a very similar wash and is on sale for $99!

Sneakers seem like the obvious choice with a hoodie, even a cashmere one, and I like how these have little leopard detail on the heel for added interest.

My exact shoes are sold out, but there are lots of new styles of the P448 John to choose from, and most are 25% off at Nordstrom right now, including the ones with the python accents.

Vince rolled edge wool & cashmere hoodie // rag & bone Cate skinnies (similar here and here) // P448 sneakers (25% off) // similar pearl studs

I don’t have any pictures from Thursday. I was feeling kind of craptastic (#girlyproblems) and I spent the entire day at home, cranking out blog posts.

That brings us to Friday, and it was rainy and dreary outside. I had a workout appointment, and then I came home and showered off and threw on a matching sweatshirt and sweatpants to go see my chiropractor.

I wore my white leather Vejas because rain, and I threw on my new The North Face jacket!

Yes, I decided to keep the white. Everything here is true to size.

Lou & Grey sweatshirt and sweatpants // Veja Esplar sneakers // The North Face quilted jacket // Lagos earrings

Becca asked to go to the mall on Saturday afternoon, and it doesn’t take much arm-twisting to get me to the mall, so we went after I got back from my run.

It was sunny but chilly, and I didn’t want to deal with a coat, so I decided to wear this faux suede draped jacket over a white tee with jeans. I chose a lighter denim wash since the jacket and top are both so light.

I first tried the outfit on with my snake print mules.

They’re cute with it, but they seem kind of dark against the rest of the outfit.

I think I’d like them better with my faded black jeans, which I could have worn, but I didn’t think I could walk in the mules all day, so I switched to these light grey booties.

I love the color combo, but the jeans are a tad too long for them.

It’s not a deal breaker, but I don’t like how they fall inside the booties. I’m especially aware of it since writing the post where I updated older outfits.

I thought my rag & bone Cates might be shorter, so I did a quick denim switcheroo.

And nope! Even longer. I guess I cut more off the AG Farrahs than I realized. #ooops

I decided I liked this shade of denim better with the outfit, so I kept the jeans and tried a cuff…

It’s okay, but I’m not loving it. And to be honest, these booties are comfortable, but they haven’t been sufficiently broken in, and our mall is HUGE. I wasn’t sure I could handle that much walking in them. I’m out of practice, thankyouCovid.

Then my eyes landed on these snake print booties. They have a lot of cushion in the footbed, and they’ve seen a lot more wear and tear than the rag & bones, so they’re well broken-in and very walkable.

These booties look a lot better with the length of these jeans because of the lower shaft, but I just wasn’t feeling the snake print with this outfit. They looked dark and heavy to me against the light tones in the rest of the outfit.

So I went back to my closet, and my eyes landed on these sneakers.

I know, I wear these too much, but look how perfectly they work with the outfit!

The light grey and white tones complement the light grey jacket and white tee, and there’s low contrast against the light wash jeans, so the entire outfit looks very cohesive and almost monochromatic. Then the leopard tab is a fun little pop of something-something.

The whole look is casual-cool and comfy, but polished and put-together. Plus, the sneakers are super comfy and easy to walk in.

My days of wearing heels to traipse around the mall may be over forever.

BlankNYC jacket (size M) // Banana Republic slub tee (size M) // rag & bone Cate skinnies (TTS) // P448 sneakers (25% off) // hammered silvertone hoops // compass pendant

We got back from the mall just in time to change to go to a friend’s house for an outdoor get-together. I knew I’d be too chilly in the outfit I’d been wearing all day, so I switched into this cozy leopard sweater from last year (on sale at Saks Off Fifth) and my go-to off-black jeans.

I added my Vince Chelsea boots from the #NSale, excited to wear them for the first time. But something about the jeans and boots combo just wasn’t working for me. This happens every time I try to wear these boots.

The booties have a tall, slim 5″ shaft, and the jeans just seem to cut off at an awkward place.

Also notice how the leg opening of the jeans appears to be a lot wider than the shaft of the boot, so it chops up the line of the leg, even though it’s all the same color.

I’m not sure if I’m thinking too hard about it, or if I need a different style of pant, but it’s frustrating b/c I love the boots, and I was sure I’d be wearing them a ton this fall and winter.

Here’s a close-up of the side view — the hem of the jeans kind of gets stuck between the heel tab and my leg, and then they fall over the front of the boot, so I don’t think longer skinny jeans would work because they wouldn’t quite fit over the shaft.

Maybe I need a slightly longer straight-leg style… or a shorter skinny?

Or maybe I should just stop over-thinking it and wear these together already.

I wasn’t ready to give up yet, so I tried a lower shaft (3 1/2″) taupe bootie, but this is even worse. (You can tell by the look on my face I’m not feeling it, lol!) I definitely prefer a black boot with this outfit.

So then I tried these black leather Chelsea boots with a 4 1/2″ shaft.

At this point, you may be thinking, why a Chelsea boot?

Well, they’re what I have, and they’re very on trend right now. But I confess, I always struggle with styling them.

I’m not sure why I can’t make them work, but I’m beginning to think the jeans are the issue in this case, not the booties.

Again, the side and back views aren’t so bad.

It’s only the front-on view where I see that line of demarcation between the booties and the jeans that bothers me, but overall, I’m just not loving these jeans with any of these boots.

I figured I’d go back to my safety zone and just wear mules and freeze… but I don’t even like these mules with this bulky sweater.

Don’t my bare ankles look naked and afraid against the chunky wool sweater and dark jeans?! 😂

So I threw the whole outfit away, and put on my blue jeans from earlier in the day with an ivory wool/cashmere sweater and my cozy UGGs.

The sweater is sold out, but I link it for the details, and in case anyone wants to try and hunt it down on Poshmark or eBay.

I tried adding this chocolate brown vest, but I didn’t care for how it was the exact same length as the sweater… overthinking again, probably.

It’s a cute vest, though. I like the way it’s designed in the back.

I ended up taking off the vest and wearing my white quilted jacket instead, but looking at these pictures, I think the vest was fine.

At that point, I was exhausted and too tired to think straight, and everything was looking wrong to me.

I’ve said it before, and I’ll say it again, at the end of the day, I’ll always revert to my comfort zone, even if it’s too plain. Less is more, and all that.

Whew! Okay, that brings us to Sunday.

I was tired of trying new combinations so I went for an easy, tried and true outfit.

I followed one of your suggestions and shortened this necklace, and I guess I like it.

Wearing it longer may be more intrinsically flattering, but it does seem a bit tired at the moment. I think I’d prefer two delicates better than the single pendant, but I love this piece and enjoy wearing it, so I’ll probably continue to wear it shorter for now.

And I am totally loving these shoes, by the way — definitely a splurge, but well worth the investment at 50% off.

The soft Italian leather feels so luxurious, the shape is flattering and feminine, and the delicate studs give them just a bit of an edge but still keep it classy.

They break in easily, but definitely size up half. I went for the 8 1/2, and they were a tad snug in the toe box when I first put them on, but after wearing them for half the day on Sunday, they feel like I’ve had them for years.

BR bell sleeve sweater // Good American Good Legs skinnies // AGL studded flats (size up half) // Yurman crossover necklace & cable hoops // croc print tote c/o Ann Taylor

I spent the better part of Monday doing try-ons for Saturday’s post, and when I was done, I threw on this comfy hoodie and crop jeans with my favorite sneakers for the rest of the day.

Yes, I’m aware that I over-wear these sneakers, but some weeks they just seem to go with everything.

Also, my Paige crop skinnies are on 20% off. I love the wash on these and the tattered hems, and they are soooo soft and comfortable.

This pair is similar and on an even better sale; the wash looks more similar to my rag & bone Cates.

Treasure & Bond v-neck hoodie // Paige Hoxton crop skinnies // P448 sneakers (25% off) // Lucky Brand earrings // Madewell necklaces

And then there was yesterday. In the interest of keeping it real, I didn’t change out of my workout clothes. I just wasn’t feeling it. Some days are like that.

Both the pants and top are Zella from Nordstrom, but I don’t have links because they’re older styles.

I’ll actually be doing a few sponsored posts with Zella in the coming weeks, so if you have anything in particular you’d like to see me style, let me know! I’m going to start sourcing products for the first post this week. Are you interested in outdoor workout gear, gym outfits, loungewear, athleisure looks? I’d love for these posts to be a helpful resource.

Finally, I want to show you one of Becca’s outfits because right now American Eagle has 30% off sweatshirts, joggers, and leggings. I shared this on Sunday, but in case you missed it, the 30% off sale ends tonight.

She fell in love with this oversized sherpa lined hoodie when we were shopping for her birthday, and she’s already worn it a couple of times. I think it’s so cute on her too. The sherpa lining is ridiculously soft, and the long side slits and oversized styling are perfect for wearing with leggings. (She is 5’5″ and has the XS, for reference.)

It would make a nice gift for any teen girls or young adult ladies in your life, or if you’re looking for something super casual and comfy to throw on with skinny jeans or leggings, this might be for you!

AE sherpa lined hoodie // Core 10 leggings // Adidas Superstars

She also snagged this oversized stripe sweater (in the XXS) and this oversized stripe sweatshirt (size XS), in case you’re looking for more ideas for the younger set.

I also want to let you know that a few more sizes popped up in this popular Caslon utility jacket. I have it in the small, but it’s a tad snug in the shoulders. I would suggest sizing up if in between sizes.

And this year’s version of the J.Crew NYC tee has been restocked in all sizes. It’s final sale, but it’s 30% off the markdown price, so there’s not much to lose. You can always consign it if it doesn’t work out.

I recommend sizing up if in doubt; mine is the medium. It’s last year’s version, so may not be sized the same, but if in doubt, it’s always best to size up.

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37 thoughts on “What I Wore Lately Vol. 30

  1.  As the person who suggested shortening the necklace, I have to say I love the length!  It’s so hard to notice new trends in jewelry for me but I recently caught on that the halfway to the belly button length I had worn for many years was out of style. Either just above or just below the bra line looks much fresher right now. I also love your madewell double necklaces. So pretty! 

  2. I’m looking forward to the Zella posts! I know that I only can speak for myself, but I already have a good handle on what I like to wear to the gym (or to run in). But I’d love to see how you style some Zella pieces for activities like hiking to spending time outside. As a general rule, I don’t like to wear more delicate gym clothes to hike in–I worry that they might snag. And I like to see how to wear layers, since the weather can vary.

  3. I love this post because it is exactly how I sometimes end up with a totally different outfit than the one I began with!  You keep it real, girlfriend!  I think it is the jeans–you need a wider bottom for the chelsea boots or shorter jeans. I did love that brown vest–I’m excited that brown is coming back–we were wearing grey for so long…  And PSA, P448.com has the python sneaks for like $135 and free ship/return.  And many other styles on super sale. Keep doing your work Jolynne!  You make us happy!

  4. Another great post! Becca is ready to step in your shoes! 

    Regarding the Leopard sweater and boots not working- I know you don’t want to hear this but it’s the jeans; crop flare would work or at very least straight leg. I think the more you wear them the more versatile you’ll find them. They are not as odd looking as we think, we just need to get used to them. 

    Do you have combat boots? If so, could you do a short segment on different ways to style? Or maybe Becca ? 😊

    Thanks as always 
    Bernadine

    1. Becca says she could never do what I do, ha! She thinks all the try-ons seem horribly laborious, which honestly, they are. But I do enjoy the final outcomes. 🙂

      So I do think you are right that the straight or crop flare would work better with these boots. Although I have tried the crop flare and also felt it looked weird. So maybe the straight ankle? I don’t have that many jeans of those styles to play with, but I have a few. I will try some other options this week.

      I do have what I call hiker boots, but Paul calls them combat boots… they’re sort of a crossover, I guess. These: https://shopstyle.it/l/bnCN5

      I love them but I think I bought them too big so they always make my feet look huge.

  5. I think my favorite part about this post was your outfit evolutions. I’m always curious about the thought process behind finished outfits. I have a similar style of black boots that I haven’t figured out how to wear with pants because they just look weird, but I like them with dresses and skirt outfits a lot.

    1. Yeah, I think the process is so interesting. I’m glad others do too! I can see how the Chelsea boots would work well with skirts and dresses, I just don’t wear them that much.

  6. As for the Zella posts, I’d love to see cold weather outdoor items. Covid got my husband and I walking so much more than ever before and I’d love to keep it going through the winter. After years of only gym workouts, I have nothing for cold weather. On another note, I just wanted to say thanks – I get compliments on my outfits all the time, which is hilarious to me because I am not really fashion-y at all. I tell people about your blog (and a few others I read) and how you all keep me current and knowing how to put my clothes together each day. 🙂 

  7. I know I say it every week, but this is one of my favorite posts because it reminds me that even fashion bloggers have outfit challenges at times.  I like what you ended up wearing to the gathering with your friends.  I really like the UGG booties and recall you saying how much they feel like you have on slippers.  I hope you are having a good Hump Day!

  8. Hi Jolynne, 
    Great post today. I am in need of clothes to wear outside; walking, running. I also exercise at home and am in need of tops. 
    Your posts bring joy to me. Please know your hard work is appreciated. 

    Deb

    1. Yes, for sure. But it depends on the styling. More of an oversized look is in style right now. I almost never wear collared shirts b/c they irritate me. I think it has something to do with having shoulder length hair.

  9. Hi Jo-lynne,
    I am not familiar with the Zella brand athletic wear. I am currently looking for a long sleeved medium weight shirt for running. Would love it if you could include a couple in your Zella post.
    Also want to add how much I enjoy your “what I really wore” posts. So helpful!

    1. I need one of those too! I actually had a Zella one from last year that I loved, and I ripped it or stained it or something bad enough that I had to get rid of it – I was so bummed. 🙁

  10. Love this analysis on the looks. I get analysis paralysis with outfits…. Have my tried and true outfits. As for the Stella ideas: I’m interested in the indoors, gym or athleisure looks. We are getting an inch of more snow today (ugh!) so outdoor looks are wasted on me. Its parka and boots time. We seemed to have skipped fall.

  11. Thank you for sharing your trials with pairing jeans and booties. This seems to be an almost daily struggle for me and I invariably choose sneakers in the end, even though I love my booties! Maybe another post addressing this issue is necessary.

  12. First off. I liked the taupe bootie with the leopard sweater and black jeans. I think it was the jeans that were the problem, not all the booties. Jeans looked too long. This is what I go through a lot. Can’t seem to have the right shoe for anything. 
    Second I’d like to see some athlesure  outfits for the zella post. Or loungewear. Wear at home stuff.  Also more sweaters without wool….. not cardigan style but shorter that aren’t boxy. Not liking the boxy short styles this year. I use to love LOFT sweaters but they’ve gone so short and boxy. 

  13. For your “outfit evolution” above, not sure why you didn’t try on the black AGL loafers with that outfit. They would’ve looked great I bet. Or a dark taupe loafer. I agree that the black mules didn’t look quite right, but a loafer flat looks more complete I think and might’ve tied the whole outfit together. Or even your p448 sneakers would’ve been cute. The outfit you ended up in looked comfy and cute though too. 

    1. Yep, I just explained to Judi that I didn’t want to wear the AGL to this event for 2 reasons, but I should have tried them just for the heck of it to see if they worked. And my feet were exhausted from wearing the P448s all day, so I didn’t want to wear those again. 🙂

  14. So i really liked the leopard sweater and black jeans….wondering why you didn’t put on the pointy toed studded loafer with the outfit ? Would have been a cute option. I agree with others about the Chelsea boot, I think it needs a cropped flare/straight jean. I think that jean style is so cute on you the times you’ve tried them, change is hard LOL. I am a conformer and not sure I can ever wear skinny jeans again 🙂 I love when you do these posts and I it looks like very time consuming, so we thank you for putting them together for us.

    1. Funny a few of you suggested that! I did want to wear those AGL loafers – I should have at least tried them for the picture. The first pair I got had a minor imperfection, so I had ordered another pair that wasn’t in yet. I didn’t want to wear these b/c I wanted to return them without wear and tear. Also, I was going to a backyard gathering, and I felt like the AGL were a little too nice to tromp around on the grass. The Everlane loafers seem more carefree. Still, yeah, I could have put them on just to see how they would work. I was in “real life” mode – what was I going to actually wear that night. 🙂

      I do like the Chelsea boot, but it definitely needs a different style jean. Funny thing is, when I have tried them with my straighter jeans, I don’t care for those combinations either. I will play around with them and take some pix this week.

  15. Yes as others have stated, it’s the jeans that are wrong. I think you are starting to see how skinnies don’t actually work with everything nowadays. Haha! I think cropped flares or straights would be so cute and current with the chunky Chelsea boots. I actually started following Susie Wright from Portland after you did the collab together.  She has this look down and I notice that she rarely wears skinny jeans anymore. I think your eye will adjust eventually. Don’t give up on the look. 😊

    1. Yes, I know the jeans were the issue with the shoe choices, but I really wanted to wear the off-black color jeans with the top, so I had to make a shoe I have work. 🙂 And those jeans are weird b/c they have a legging fit, but a wider leg opening. So they don’t read as a straight or a skinny either. They are awkward to pair with any style of booties, I’m learning.

      I love Susie’s style. I was looking through her outfits, specifically to see how she makes the straight crop style work so well. She must have a very different body type than I do b/c she tucks all her tops and they look great. I can’t do that – I’m too short waisted.

      I’m not giving up on the straighter silhouettes, but it’s not as simple as it seems to make it all work together. So much depends on body type. I think I look better in full length straight leg styles, so you don’t have to tuck in your top to make the proportions work out.

  16. Hi! I have a question about the brown vest. Would you say it’s true to size? I need a new black one for tennis. My figure is very similar to yours.

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