May 27, 2026

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What I Wore Lately: Rainy Days & Summer Layers

Happy Wednesday, friends! It’s time for another edition of What I Wore Lately, where I share my everyday looks from the past two weeks.

This batch of outfits started out strong. I had a lot going on at first, but life has been pretty quiet lately, with very few plans, some dreary rainy days, and a handful of days when I opted out of “looking cute.” That said, I realized even my most casual outfits still fit my style goals, so even when my hair and makeup aren’t done, I like what I’m wearing and still feel somewhat put-together.

If you’ve been listening to Jen’s podcasts this spring, you know she talks a lot about this very thing—making style a habit and having the right pieces in your closet so you can get dressed for your real life and like the result, no matter what’s on the agenda. That really resonated with me.

So with that lengthy preamble, here’s what I’ve been wearing over the past two weeks! Hopefully you’ll find a little style inspiration along the way.

Two Weeks of Everyday Spring/Summer Outfits

I had plans to meet a friend for lunch two weeks ago today, so I took the opportunity to dress up a bit. Of course, for me, that still may involve blue jeans! I love how this light wash pairs with this sweater.

The jeans are a smidge too long to work as ankle length and definitely too short to be full-length, so I like wearing them with a bit of a heel. These jelly slide sandals have a 2½” heel, which is perfect for giving me the height I need while still being very walkable.

Melissa Nepton Jane Sweater (S) // PAIGE Stevie (30) (also at Nordstrom) // Dolce Vita Galae Heels (8) // Dolce Vita beaded bag // Astra Pavé Paperclip Necklace & Isla Gold Bead Necklace c/o Thatch // Raven Resin Bangles c/o Baublebar // similar hoops

The next day, I wore this sleeveless polo sweater with trouser jeans to go see Chicago in downtown Philly. It felt a bit chilly for open-toe shoes, and rain was in the forecast, so I added leopard slingback pumps for a bit of fun. I’ve had these for a few years, and while I don’t wear them often, they’re perfect when I want to add a little personality to an outfit.

Also, PAIGE is still having their 25% off sale, so this sweater top is included! It’s a really nice quality piece—on trend, but also classic enough that I know I’ll be able to have it for a few seasons.

I added this cropped trench to have a light layer in case the theater was chilly, and also with the rain in mind. Thankfully, the rain held off until we were driving home, but it was nice to have a layer walking to and from the theater.

PAIGE Vesta Top c/o (M) (also at Nordstrom) // J.Crew Denim Trouser Jean (29) (option) // Sam Edelman Bianka (8.5) // Benny Cropped Trench (M) // Marlyn Schiff Ophelia Bracelet c/o

I kept things casual while working from home the next day in a linen tank and these old Athleta cargo pants.

Athleta Getaway Linen Blend Muscle Tank (M) // Brooklyn Heights High Rise Cargo Pants (6) // On Cloud 6 (9)

Later on, I changed to host the boyfriends for dinner. (It’s so nice having Becca back home for the summer!)

This look is so simple, but I love it. I feel like the combination of the raw hem wide-leg jeans with the rhinestone-embellished jelly flip flops is the perfect casual summer denim-and-shoe pairing. And the green tee is fresh and bright, but still fairly low-contrast against the mid-wash jeans, which makes the whole look feel really balanced. Something about it is just very pleasing to the eye.

I kept the accessories simple since I’d be cooking, but if I were wearing this out somewhere, I’d probably add a belt and maybe some kind of fun statement piece. Also, the PAIGE Anessa jeans are still on sale! They’re my favorite wide-leg style for pairing with flats.

EVEREVE Nora (M) // PAIGE Anessa (30) // Loeffler Randall flip flops (8)

That Friday, I had a mani/pedi appointment and a facial, so I just wore some of my favorite comfy Vuori pieces all day.

Vuori Energy Top Long (M) // Vuori Modern Straight Leg Pant (M) // Vuori Performance Hoodie (M) // Madewell Iggy Thong Sandal 98)

We went out to dinner the next night. It was a nice spot and a Saturday night, so I decided to dress up a bit. I think black linen feels so elegant in the summer. (This is the same Tommy Bahama shift dress I have in the floral print, just in solid black.)

I paired it with gold strappy sandals, and I debated carrying my red bag, but I ended up going with a raffia bag with gold hardware to keep the look light and summery.

Then I layered some delicate jewelry and added a gold cuff to keep it feeling dressed-up and classy.

Tommy Bahama linen shift (M) (option) // PAIGE Ella (8.5) // Rebecca Minkoff Edie // Astra Pavé Paperclip Necklace & Isla Noir Bead Necklace c/o Thatch // Lili Claspe Adva Cuff // similar hoops

I kept it casual for church the next day in this navy sweater tee and light wash jeans. I was in a rush, so I just grabbed the raffia bag from the night before and threw on these Veronica Beard slide sandals I had recently pulled up from storage in the basement. I got them last year, and I still love the strap design and stud detailing.

Splendid Christa sweater (S) // PAIGE Stevie (30) (also at Nordstrom) // Veronica Beard Via (8) // Rebecca Minkoff Edie // stretch bracelets // similar hoops /

I didn’t get around to taking a picture of my outfit until I got home, and as soon as I saw it, I realized these jeans are really too long with flat sandals. It isn’t terrible, but I threw on these Margaux block-heeled sandals to compare, and I feel like the difference is pretty noticeable. These jeans just look so much better with a low heel.

Also, the raffia bag is fine—it’s a neutral, of course, and it even has darker brown leather on the straps that ties into the color of the sandals. But I feel like a darker bag, closer to the color of the shoes, would work even better. Such minor details, but while we’re picking this outfit apart, we may as well go all the way!

And speaking of small differences, I also wish I’d added a necklace, maybe my larger Jane Win Hope coin pendant.

Then I decided to take it one step further and see how the Madewell Jules would look with the same sweater and the flat slides. Sure enough, they worked much better!

The difference is subtle, but the slightly slimmer silhouette, slightly shorter length, and maybe even the slightly darker wash (which creates less contrast) all work together to pair better with flats. Interesting how such small differences can make such a big impact.

Okay! Moving on… I hosted a friend at our backyard pool later that afternoon, so I threw on a tank top and shorts over my swimsuit.

Talbots swimsuit (M) // Lilla P tank (M) // PAIGE Olivia Short (30) // Madewell Iggy (8) c/o

I had a photo shoot the next day, and afterwards I went to a coffee shop to work for a bit. I just kept on the last outfit we photographed—the brown linen pants with the green ribbed top and Steve Madden jelly sandals.

Michael Stars Jinny (M) // KUT Meg Linen in Chocolate (8) // Steve Madden Tracie Jelly Sandals c/o (8) // EVEREVE Hudson belt (M/L) // Maison de Sabre tote c/o // Jenny Bird Doune Hoops c/o // Stella & Dot Multi Rondelle Necklace // Madewell cuff

I thought I liked the look, but the same thing happened as the day before, just in reverse! I took a photo when I got home and realized these pants look a bit short with the heels. I actually liked how the photos Alison took turned out, so maybe it works, but I tried them on with flat thong sandals just to compare, and sure enough, I like these pants better with flats.

I also think I prefer the simpler lines of the top untucked. These pants have a very high rise, and while I like the finishing touch of the matching brown belt, I feel like my proportions look better without the tuck.

Here’s a side-by-side to compare. What do you think?

After I got that all sorted out, I changed into a more casual, comfy outfit for the afternoon. These Ruti On The Loose Work Pants just arrived in the Walnut color, and I love them. I went up a size for this pair, since my black ones in the size 8 are snug at the waist and sometimes wrinkle a bit across the back.

Because of the volume in the leg, I feel like they need something more fitted and sleek on top, so I paired them with a simple black tank—the Lilla P slub scoopneck tank I found in Sarasota. It’s such a nice quality top, and even though the outfit is super simple, I feel like the quality and fit of both pieces work really well together.

Lilla P tank (M) // Ruti The On The Loose Work Pants (10) // Madewell Iggy (8) // Jenny Bird Doune Hoops c/o // Stella & Dot Multi Rondelle Necklace

Someone asked me for more ideas of things to wear with these pants other than a black or white top, and honestly, that’s how I like them best. I’m not one of those people who has to be able to wear something five different ways to justify its place in my closet. If I like it best with a black tank, I’ll probably wear it with a black tank 95% of the time.

In fact, same goes for olive! I almost always wear olive with a black top. Case in point… the next day, I wore the olive PAIGE Olivia cargo shorts (25% off!) with this black Free People ribbed henley tank to work from home all day after my morning workout.

This top would also be really cute with those walnut Ruti pants, by the way. Changing up the style of top is enough variety for me!

Free People Jamie tank (L) // PAIGE Olivia shorts (30) // Madewell Iggy flip flops (8)

The next day was another casual WFH day after a Pilates class that morning. My hair is piled on top of my head because I took a quick pool break that afternoon, and I threw on this graphic tee and denim shorts afterwards.

This tee is on sale, by the way! I think it’s so fun, and I love the MOTHER Goodie Goodie tees. They’re pricey, but they hold up really well. I always size up to a large, though, because they run small and tend to shrink a bit.

MOTHER Little Goodie Goodie Tee (L) // KUT from the Kloth Jane High Waist Denim Shorts (8) // TKEES Lily Nudes in Au Naturale c/o (8)

Last Thursday, I finally had a reason to fix up and get dressed again! I met a friend at the mall for lunch and shopping, so I pulled on the old faithful Madewell Jules with this cute sleeveless collared sweater in the rugby stripe. Because the top feels a bit sporty, and because we’d be doing a fair amount of walking, I went with sneakers.

I recently grabbed this pair of Gola sneakers because I love the cotton mesh for summer, and the combination of white and camel is a nice update from plain white sneakers.

Velvet Zoella Sleeveless Collared Sweater (M) // Madewell Jules (29) // Gola Tornado Zephyr Sneakers (8) // Quince bag // Jenny Bird Doune Hoops c/o // similar necklace // Yurman bracelet

Last Friday was another WFH day after a Pilates class. I did some try-ons and wore this simple outfit for a while.

Z Supply tank (L) // Paige Anessa Twisted (30) // Birkenstock Sydney (39) // Bryan Anthonys MOM coin pendant & You Are My Light Necklace – 20% off with JOLYNNE20 c/o // Jenny Bird Duone Hoops c/o

Later on, I changed back into the Ruti pants, this time with a black linen tank. I also wore the Madewell Iggy sandals again. I like how the black footbed grounds the outfit, while the white leather straps keep it feeling light for summer.

Athleta Getaway tank (M) // Ruti The On The Loose Work Pants (10) // Madewell Iggy flip flops (8)

I have no photo evidence of last Saturday. It was cold and rainy, and we all hunkered down at home. I spent the day cleaning out and organizing my bedroom and bathroom.

On Sunday, I rallied and got dressed in a casual red, white, and blue outfit as a little nod to Memorial Day. This red-and-white striped sweater has been a favorite this spring—such a nice quality classic. I paired it with the Madewell Jules and added cognac shoes and a matching bag for a warm contrast. I topped it all off with my Sam Edelman trench because rain.

Sam Edelman trench (S) // Michael Stars Mikaela sweater (M) // Madewell Jules (29) // Jeffrey Campbell Fathom Flats (8.5) // Mulberry bag // Yurman hoops

Monday morning was still chilly and rainy, so I pulled on a different striped sweater and the old faithful Madewell Jules to run to the store and pick up food for our Memorial Day gathering. This time I opted for sneakers, and I grabbed the Sam Edelman trench since it was still sitting out.

I actually kind of like this look, although I probably would’ve gone with my off-white Lululemon raincoat if I’d gone to the coat closet.

Sam Edelman trench (S) // J.Crew Factory beach sweater (M) // Madewell Jules (29) // Dolce Vita Sariya sneakers 8.5

By the afternoon, it was warming up and getting quite humid. Plus, I was hot from running around prepping the house and deck for company, so I changed into shorts and a top before our guests arrived. I kept the blue-and-white stripe-with-denim theme going!

Splendid Kylie tee (M) // KUT Jane shorts (8) // Madewell Iggy flip flops (8) // Yurman hoops & bracelet

Finally, I went back to the green ribbed top, olive linen pants, and rhinestone-embellished jelly sandals to host our church small group last evening. I really should have added a bolder necklace and a bracelet, but it was a casual gathering and a long day, lol! I do really like the overall colors and proportions of this outfit, though.

Michael Stars Jinny (M) // KUT Meg Linen in Chocolate (8) // Loeffler Randall Taryn Brown Jelly Flip Flop (8) // Yurman hoops

And that wraps up this round of everyday outfits. Thanks for following along!

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23 Responses

  1. Hi, too, like your chocolate linen pants with the shirt untucked. I wonder if it’s because a belt feels heavy on linen? I only have the Joelle linen pants this season and they have a tie so adding a belt isn’t an option. Little details to consider 😊
    I read the term ‘elevated ease’ recently and I immediately raised my hand. I think that falls in line with your Ruti pants look. Each piece is a quality elevated basic (my preferred daily look) so it simply works and appeals to your eye while looking like you invested, time and money, in getting the easy look just right.

    1. Love the term elevated ease. Yeah, the belt with the linen pants was a bit heavy but Alison and I debated and felt like they looked unfinished with the front tuck and no belt. I do have a lightweight woven style from Madewell that might look better with linen.

  2. In your side by side I definitely like the photo on the right with the lower slide and untucked!
    I know what you mean about getting dressed and something just looks off and the most simple change can make a big difference.. I was exactly that way yesterday getting dressed to run some errands. I didn’t want to look too dressed up while keeping it casual and also fighting with the weather.. cooler when I leave warming up while I am out.
    Would you wear your Ruti pants out for errands? And what sneaker would you put with them if any?
    I had ordered the ALO trouser pant loved them ( in fact they brought them in lengths finally ) but made a swishing sound so back they went.
    Thanks for your detailed what you wore and keeping it real.

    1. I’ll definitely wear my Ruti pants out for errands. I wore the black pair traveling too. I need to try some of my sneakers with them. Something low profile and neutral, for sure, but not stark white.

  3. Love all these outfits, thank you for sharing! I recently bought the KUT Meg and have worn them alot especially on a trip to the Pacific Northwest. I am going to check out the linen version, thank you for sharing those. I tried the Paige Anessa (ordered and returned) and really did not care for them? It seemed like there was too much fabric…not sure how to describe it? What might be the difference between them and the Meg-just curious. Maybe I should try the Paige Anessa on in store lol

    1. It’s really just a matter of personal preference. And it depends on the proportions of the outfit and how those interact with your personal body proportions. There is no simple rule, sadly.

  4. I thought of you, Jo-Lynne, when I was running errands a couple days ago. I had on kick-flare loose ankle jeans, a loose sweatshirt-style top and sneakers. I caught a glimpse in a store mirror and realized I looked like a blob! The top was too big for the jeans, so I did a front tuck which helped. I also realized that sandals would’ve been better. Well, I won’t wear that combo ever again! 😆

  5. Great post! The tweaks you made with the two outfits really did make a difference. Noted and filed!

  6. Love the side by side comparisons (definitely liked those chocolate pants better with flats) and the outfit evolution discussion. I’m slowly training my eye to notice those small details and they do make a difference.

    A small rant on the Ruti pants….they look great on you but appear only slightly shorter on the website model who is supposed to be 5’10” – No way! I’m 5’10” and I’ve fallen for this type of thing so often only to purchase something and find that it is way shorter on me than the model. I’m thankful they have the inseam measurements because that is so much more helpful to me than the pictures. Perhaps they’ll come out with a tall version – they look like comfortable and versatile pants.

      1. I think you’ve experienced a similar thing – sometimes reg length works best for you and sometimes petite length works best. Same for me only its reg vs tall length. I think its time for me to lean more into getting things hemmed to get the exact length I want – the flats vs heels discussion just proves that the length and shoe pairing do really matter.
        Oh…and I think the chunky-ness or slimness of the shoe (tennis shoes particularly) really matters too. Vamp? Is that how much of the foot is covered? Thanks for teaching us to notice these small details!

  7. I like the yellow/white tank from Evereve–still on the fence–I know you sported it b4 and I liked. I don’t know if I can pull off light yellow–yellow shades are tricky on me–since I’m a blonde. But maybe the white trim will help.
    Jo-Lynne–I rec’d a nice gift card for Evereve for Mother’s Day–if you can, can you tell me your favorite thing from there, that you wear on repeat? I love Evereve!

  8. Hi, there!

    Would you mind sharing what color wash the Madewell Jules jeans are?

    Thanks!

    Lisa

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