Hi friends, happy hump day! It’s time for another edition of What I Wore Lately, where I round up my daily outfits from the past couple of weeks. I have a lot of great pieces right now, but I’ve been struggling to put them together into outfits that make me happy. I’m sure a lot of you can relate.
Transition season is always challenging to dress for because not only is the weather somewhat limiting, but we have to figure out new outfit combinations with the new additions we’ve made to our wardrobes. Add to that, shoe and pant silhouettes have really shifted lately, so putting it all together can often feel like an exercise in futility and frustration.
I’ve been taking lots of pictures of my process lately, so if you enjoy that kind of post, grab another cup of coffee and get ready to scroll. You might be here for a while.
What I Wore: Two Weeks of Everyday Outfits
SIZING NOTES: I’m 5’5″ and I usually wear a small or medium in tops and dresses, a 29 in jeans and pants, and a size 8 shoe. Gifted items are indicated by c/o; everything else I purchased myself.
I wore this simple look to run out to an appointment one morning. These MOTHER Dazzler slim straight ankle jeans are one of my all-time my favorites for casual looks because they’re soft and stretchy, and they look good with sneakers and flip flops. They’re also 25% off at Saks right now! I also like this pair for a finished hem.
Lucky Brand sandwashed shirt (S) // MOTHER Dazzler – 25% off (29) (option) // beek flip flops in silver/beach (8) // AllSaints bag // Lagos hoops
It was a warm day, so I came home and at out by the pool with a friend for a while, and then I changed into shorts and a tank top for the rest of the afternoon. This washed black ribbed tank is on sale at Evereve, and my shorts are on sale at Bloomies.
Remi Rib Tank – on sale (M) // AG Becke – on sale (29) // beek flip flops in silver/beach (8) // Lagos hoops
I went to the mall to grab a few things the next day, and I decided to use the opportunity to put together a new outfit. It was the week after Labor Day, and I was ready to start wearing my some of the new transitional pieces I’ve been purchasing.
I wanted to wear this red top, and I tried it on with wide leg cuffed jeans, for something different than the flares and straight leg jeans I usually gravitate to. I felt like the outfit needed a black shoe, so I grabbed these sleek black ankle boots to give me a little height, but I’m not sure I like how these pieces work together. I tried the top front tucked and untucked, and I think I like the tuck better with these jeans, but overall, I felt a little silly.
Marci top (S) // KUT Sienna (6) // Franco Sarto boots (8)
I went back to my closet and pulled out these dark wash wide leg jeans with the front patch pockets, and this time, I tried the look with silver flats. I think it works and my eye just needs to adjust, but I still felt a little silly. I also felt myself needing a black flat option in my fall closet, so I added that to my shopping list.
Marci top (S) // KUT Meg (6) // Sam Edelman flats (8.5)
I ended up going back to my tried and true MOTHER Rider, a deep wash straight ankle jean that is 40% off at Nordstrom right now! I left the top untucked and added leather espadrilles, and off to the mall, I went! This felt a lot more authentic than the other two looks, and more practical for shopping.
Marci top (S) // MOTHER Rider – 40% off (29) // similar espadrilles
The next day when I went to get dressed, I once again challenged myself not to reach for the same old MOTHER flares and straight leg jeans, and I pulled out these PAIGE Anessa wide leg crops.
I like how a shorter v-neck sweater vest looks with wide leg jeans, so I grabbed this stripe tank and added coordinating taupe sandals. It’s simple, and I like it, although it does still feel quite summery to me. It was a warm day, so I just went with it.
Reese Stripe Tank (S) // PAIGE Anessa (29) (option) // similar sildes // Jenny Bird bangle // love knot earrings // similar link necklace
I had a lunch date with a friend the next day, and I pulled out that red top again. When I went to the mall, I purchased these Franco Sarto pointy toe slingbacks to help solve my outfit-making frustrations, and I love how they look with the washed black slim straight leg jeans and the printed top.
Marci top (S) // AG Mari (29) // Franco Sarto flats (8.5) // similar silver hoops // Yurman bracelet // YSL bag (option)
Those AG Mari jeans tend to get tight in the waist when I eat, so I came home and changed back into my most comfortable jeans. Just for fun, I tried the outfit with those silver flats, to see how I liked it.
I guess it’s okay but I feel like the dark top looks better paired with darker jeans. The silver flats and light wash flares work together okay, though, so I’ll try to remember that shoe + pant combo for future outfit-making endeavors!
Marci top (S) // MOTHER Weekender (29) (25% off this finished hem option) (option) // Sam Edelman flats (8.5)
We were supposed to go visit Paul’s mom that night and bring pizza, and I just wanted to be comfortable. (It’s about an hour’s drive.) So I swapped the red blouse for this hooded muscle tee, and the silver flats for my trusty Birks. Also, these MOTHER Weekender jeans with the raw hem are selling out, but Saks has 25% off this finished hem option in a similar wash, which I like a lot.
Cruz Sleeveless Hoodie (M) // MOTHER Weekender (29) (25% off this finished hem option) (option) // Birks – 20% off (39) // layer necklace // silver hoops
The next day, we had tickets to an outdoor concert, but it rained all day and didn’t look like it was clearing up, so we decided to bag it and go out to dinner with friends. Once again, I went to put a new outfit together, but I didn’t have a whole lot of time to experiment.
It was a casual restaurant, but I still wanted to wear something I wouldn’t wear around the house, so I grabbed this smocked tee and tried it with these full length wide leg jeans. I love these jeans, but they’re just a smidge too long to wear with flats, so I never really reach for them unless I’m going out somewhere that I can wear a bit of a heel. These Franco Sarto booties have a nice streamlined shape and a low heel that didn’t feel too dressy for the casual venue but leveled up the look.
I like how this outfit turned out. It’s super simple, but the smocked texture on the top makes it a little more fun and interesting than a plain tee, and the wide leg jeans look current without being too dramatic (like the cuffed ones I tried above.) I also brought a jacket along in case I got cold inside the restaurant, but I didn’t need it.
Evereve Camp Jacket (S) // Vince smocked tee (M) // MOTHER Hustler Roller Skimp – on sale (more sizes) (29) (option) // Franco Sarto booties (8) // Yurman bracelet // silver drop earrings
Okay, so the next day was Sunday, and we had church. I decided to branch out from jeans and wear a denim skirt. I tried it first with this ivory sweater vest and a utility jacket, and I also took a picture without the jacket to see if I like it okay if I needed to take the jacket off. I feel like it looks really boxy and plain without the jacket, but with the jacket, it sort of works.
KUT Zinnia (S) // The Reset Too Good Tank (S) // KUT Brea skirt (6) // similar slides
I guess I wasn’t feeling it because then I tried red pointy toe flats and my black jacket from the night before. This definitely didn’t excite me. The black jacket looks really harsh with the light denim and ivory top, and I’m not sure how I feel about the shoes with the skirt.
Evereve Camp Jacket (S) // The Reset Too Good Tank (S) // KUT Brea (6) // Sam Edelman flats (8.5)
I decided to ditch the jackets and try this sweater vest, but it’s really boxy, and the skirt already has a way of making my bottom half look like a big rectangle, so this combo doesn’t really do much for me.
Willa Lady Like Vest (S) // KUT Brea (6) // Sam Edelman flats (8.5)
I decided to swap the skirt for wide leg jeans and see how I felt about that, so I pulled out these PAIGE Anessa full length wide leg jeans I’ve been holding onto from the #NSale. (They’re on sale again, by the way!)
Willa Lady Like Vest (S) // Paige Anessa – 35% off (29) (option) // Sam Edelman flats (8.5)
I still think outfit looks boxy and shapeless, so then I grabbed my Lara Twist Muscle Tee and put it on with the PAIGE wide leg jeans and silver flats. It’s a more pleasing silhouette, but I feel like the burgundy top looks better with darker denim washes. Still, this denim + shoe combo is a good one to keep in mind.
Lara Twist Muscle Tee (S) // Paige Anessa – 35% off (29) (option) // Sam Edelman flats (8.5)
So then after all that, I went back to the ivory tank and camp jacket, but I went with leopard slingbacks to pull the black from the jacket. I feel like since the tank and denim are light, and the jacket is dark, the leopard print shoes look better than the silver flats.
Evereve Camp Jacket (S) // The Reset Too Good Tank (S) // PAIGE Anessa – 35% off (29) (option) // Sam Edelman leopard slingbacks (8.5)
In looking at that picture, I like the wide leg jeans with the rest of the outfit, but I guess I wasn’t sure about that because I ended up going back to my closet and grabbing the FRAME Le Easy Flares. I know, I’m certifiable. But I thought of them because they have a similar wash to the PAIGE Anessa, but with a flare rather than wide leg silhouette. Here’s a side by side view, for comparison purposes.
PAIGE Anessa (29) // FRAME Le Easy Flare (29)
I do think the outfit with the flares is marginally more flattering than the one with the wide leg jeans, but while the flares are certainly a current look, I feel like the outfit with the wide leg jeans looks more modern and fashion-forward, and I wish I’d accessorized them before I made a final decision.
At any rate, I decided to stick with the flares, and I added a black skinny belt. It makes the outfit look more finished, creates a little bit of definition at the waist, and also pulls together the black from the jacket and the shoes. I also added a mixed metal necklace and silver drop earrings, and I grabbed a black bag, although I think a brown bag to pull out the brown from the shoes might have been fun to try.
Evereve Camp Jacket (S) // The Reset Too Good Tank (S) // FRAME Le Easy Flare (29) (option) // Sam Edelman leopard slingbacks (8.5) // similar belt // NAGHEDI tote // silver drop earrings // similar mixed metal necklace
We went out to eat after church, and I had Paul take this picture as we were walking back to the car. I do really like how this outfit turned out, even though I feel like it isn’t as fresh and fun as some of the other combinations I was working on. The color palette is pretty basic, but the pieces all work well together to create the kind of dressed-up casual look that pretty much defines my personal style.
Evereve Camp Jacket (S) // The Reset Too Good Tank (S) // FRAME Le Easy Flare (29) (option) // Sam Edelman leopard slingbacks (8.5) // similar belt // silver drop earrings // similar mixed metal necklace // YSL sunnies (option)
Alrighty, then! When we got home, I changed into this comfy tried-and-true outfit for the rest of the afternoon.
MOTHER Margarita Tee – 40% off (M) // MOTHER Dazzler – 25% off (29) (option) // Birks – 20% off (39) // Jenny Bird hoops
And that night, we were invited over to a friend’s patio to hang out. It was starting to get chilly, so I swapped the t-shirt for a sweatshirt, and the Birks for a pair of sneakers.
Joey sweatshirt (S) // MOTHER Dazzler – 25% off (29) (option) // P448 sneakers (39) (option) // Jenny Bird hoops
Last Monday, I had an appointment to touch up my microblading. It’s been well over a year since my last touchup, and I was in dire need. It was still chilly that morning, so I pulled out this lightweight cotton popover henley.
I got it last spring, and I haven’t had a chance to wear it very much, but it’s a really nice casual top for transition season. I grabbed the same jeans from the night before, but I went for my Vince Oasis sneakers with the navy accents, to coordinate with the navy top. I really like this silhouette; the top is quite flattering. I should wear this more.
Frank & Eileen Patrick Popover Henley (Heritage Jersey in British Royal Navy) c/o (S) // MOTHER Dazzler – 25% off (29) (option) // Vince Oasis (39) (option) // Jenny Bird hoops
I had a mani/pedi appointment the next day, so I needed to wear jeans I could roll up. I pulled out this tried and true outfit, which I love. If I could live in these jeans and flip flops and just swap out my tops, I’d be perfectly happy.
Caroline Seamed Muscle Top (M) // MOTHER Weekender (29) (25% off this finished hem option) (option) // beek flip flops in silver/beach (8) // Jenny Bird hoops
I met a friend for lunch the next day… and yes, if it sounds like all I do is eat out and run errands, that’s how it feels to me too! I didn’t have much time to put an outfit together, and again, I wanted to wear something different, so I grabbed these Madewell jeans and threw them on with this top and silver flats and rushed out the door.
I didn’t even get a picture until I got back home, which is probably a good thing because if I had, I would have wanted to change, lol! Once again, I don’t love the burgundy top with the lighter jeans, and I’m not even sure I like these jeans at all.
Lara Twist Muscle Tee (S) // Madewell The Perfect Vintage Wide Leg Jeans (29) // Sam Edelman flats (8.5) // YSL bag (option) // coil earrings
When I got back home that afternoon, I tried a few more combinations with this denim + shoe combo. I first tried a lighter top, and while I like this color combo better than the one above, I feel like the sweater is too boxy with the wide leg jeans. (The front tuck doesn’t help; it just looks awkward to me.) It also looks more summer than fall.
Evereve Joelle Pullover (S) // Madewell wide-leg jeans (29) // Sam Edelman flats (8.5) // coil earrings
I don’t love anything about this next combo, the colors or the silhouette, but I do want to let you know that this gorgeous Rails sweater is 25% off at Saks! (I plan to wear it with darker wash jeans.)
RAILS Alise Stripe Pullover – 25% off! // Madewell wide-leg jeans (29) // Sam Edelman flats (8.5)
I went back to my closet and pulled out this rust relaxed v-neck sweater. I knew I wouldn’t care for this combo, but I was just curious to see a more traditional sweater with the wide leg jeans, and I also thought it might be helpful for you to see it too.
Treasure & Bond Relaxed V-Neck Sweater – 25% off (S) // Madewell wide-leg jeans (29) // Sam Edelman flats (8.5) // coil earrings
While it’s possible to wear more relaxed sweaters with wide leg jeans and look super chic, it has to be done very intentionally, and tends to work better with more dramatic pieces, like this or this.
Next, I tried this sweater vest again, and again, I feel like it’s all very boxy together. I’ve really had a hard time styling this vest; it might be time to pass it on.
Willa Lady Like Vest (S) / Madewell wide-leg jeans (29) // Sam Edelman flats (8.5)
That night, Paul and I had tickets to a live music event in town. It’s been warmer here lately, so I pulled out this denim skirt that I feel like I haven’t worn enough this season, and I paired it with this stripe sweater tank.
Reese Stripe Tank (S) // KUT from the Kloth Bristol Utility Skirt (8) // beek flip flops in silver/beach (8) // spiral earrings // Yurman bracelet // YSL bag (option) // coil earrings // similar pendant // Yurman bracelet
I met a friend at the mall on Saturday, and once again, I was trying to look cute and wear jeans other than my MOTHER Dazzlers or Weekenders… Since we’ve ascertained that I don’t care for my burgundy tops with lighter wash denim, I tried the shrunken smocked tee with these darker wash wide leg jeans, and I added my new black pointy toe slingbacks and a coordinating black belt.
Vince smocked tee (M) // KUT Meg (6) // Franco Sarto flats (8.5) // similar belt
I guess it works, but I just wasn’t feeling it. It all felt kind of tight and body-con, and it didn’t seem like a good idea to walk around the mall in new shoes.
It was a warm day, so I just ended up putting out these old favorites and going with this, and it’s probably my favorite outfit in the entire post. What does that say about me? I’m not sure. Probably that I’m not ready for cold weather, for one thing! And also, I’m a Plain Jane at heart. It’s just to easy and comfortable, but I also feel like it’s flattering and forgiving to those areas that tend to accumulate extra fluff.
Stateside Pima Slub Tank (S) // MOTHER Weekender (29) (25% off this finished hem option) (option) // beek flip flops (8) // Jenny Bird hoops // similar pendant // Yurman bracelet
I took a quick trip over the weekend because I had a family funeral to attend. I always have a dark dress at the ready for these unexpected occasions, and at the moment, it’s this Ming Wang scoop neck tank dress. I considered wearing pumps, but since it’s still warm here, I wore taupe sandals instead.
Ming Wang Sleeveless Scoop Neck Tank Dress (S) // Stuart Weitzman heels (8) // YSL bag – Triple Points (option) (option) // hoop earrings (option) // similar necklace // Jenny Bird bangle
I went back to my hotel afterwards and changed before going over to visit family that evening. This top and the jeans are both new; they’re from my trip to Evereve on Saturday, but I guess I forgot to get pictures of the top for yesterday’s Try-On Haul. I love the gold snaps on the shoulders, and it has a really nice length and shape through the body. The material is a 100% cotton slub fabric that isn’t thin or see-through at all. It’s a nice quality top.
And I think I may have found that alternative to the MOTHER Weekender I was looking for. I’ve struggled to find another brand that is as comfortable to me as MOTHER denim, and I’m so happy to have found this Pistola Lennon Crop Boot. I thought I wanted another full length style, but this crop boot style seems to work okay, and at least it’s something different!
Nation LTD. Marina Muscle Tee (M) // Pistola Lennon Crop Boot (29) // similar sildes (option) // YSL bag (option)
The next day, we met up again for breakfast before I came back home, and I wore the same jeans, but with this green mock neck top, also a new Evereve find. I also brought along my Talbots twill crop jacket; I love how the “fawn” color matches my bag and shoes.
This is also the outfit I wore for the return trip home. I don’t usually carry this bag with casual outfits, but I didn’t want to bring two, and I wanted it with the black dress, so I just carried it everywhere. As it turns out, I really like how it looks worn crossbody with more casual outfits. It occurred to me that the chain strap acts almost like another piece of jewelry.
If you also like the look and want an option for less, Quince and Kate Spade both have similar styles that would work well.
Talbots twill crop jacket (S) // Michael Stars mock neck top (M) // Pistola Lennon Crop Boot (29) // similar sildes (option) // YSL bag – Triple Points (option) (option) // Away The Carryon // similar tote
