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.
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.
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.
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.
Yes, I decided to keep the white. Everything here is true to size.
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.
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.
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?! 😂
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.
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.
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.
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!
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.
Get Email Updates
If you liked this post, be sure you’re signed up for my email updates. In addition to my most recent blog posts, you’ll receive exclusive newsletter content like special sales, my newest favorite finds, and an occasional peek behind the scenes — all delivered right to your inbox.
This post contains affiliate links. When you shop through my links, it helps support my business (at no additional cost to you) so thank you!