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Spring Outfits I’ll Be Wearing Again

  • February 24, 2026
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I am desperately awaiting for spring to arrive here in Chicago, and although we have a few more weeks of cold weather ahead of us, I’m already planning my spring wardrobe. I scoured through my archives from last year for inspiration and, in this post, I’m sharing the spring outfits I’ll be wearing again. These are simple looks – basics combined in different ways and elevated with accessories. You’ll see many of the same items repeated over and over again.


Spring Outfits I’ll Be Wearing Again

tee (similar; similar) / pants / leather flip flops (similar) / bag

A classic combination of a striped tee and white pants will definitely be repeated (with many variations). I added black accessories to this look to modernize it and add some edge. My tee is from Everlane and has limited sizing at the moment, although it still may be restocked when we get closer to spring. This one from Madewell is similar.


tee (I went up two sizes) / sweater / skirt (similar) / slingback flats (similar) / bag / sunglasses

I wore this look in March in Seattle on a mild spring day. I loved it! I’m wearing my go-to tee (I recommend going up one or two sizes), a black mini skirt, and a gray sweater tied at the waist. For shoes, I’m wearing some slingback flats but you could swap these for a more comfy ballet flat or even a low profile sneaker. Mom tip – I always wear a pair of cotton biker shorts under my skirts or dresses so I don’t flash anyone while I’m on mom duty.


black tee / trousers / old trench coat from everlane (similar; similar) / mesh flats (similar) / similar belt / sunglasses / bag

I love pairing my trousers with a simple tee and adding a jacket for a more elevated springtime look. This trench coat is old from Everlane and no longer available, but I found some similar ones.


tee (more affordable option) / trousers / gray sweater / ballet flats / bag / sunglasses / necklace / similar earrings

This was another simple look with trousers that I’ll definitely be repeating. I loved the addition of the pendant necklace (it really pops against lighter colors), the gray sweater tied at the waist, and the suede bag to bring some texture.


red tee / suede jacket (take your larger size) / shorts (take your larger size) / sling bag (ASHLEYR15 for 15% off) / flip flops / sunglasses

This red, camel, beige combo is one of my favorites. I love wearing red in the warmer months for some reason (don’t ask me why!) And take heed – there are only a few short weeks when we can wear a jacket with shorts, and I’ll definitely be taking full advantage.


tee (I go up two sizes) / jeans / python print flats / jacket / necklace / bag

I wore this look last fall, but it works nicely for spring, too. I really like pairing my more utilitarian jackets with ballet flats for contrast. I can’t wait to wear this one!


tee (I go up 2 sizes) / denim shorts / ballet flats / bag (not available now but it will be restocked for spring!) / sunglasses

This look leans more summery, but you could add a jacket or swap the black denim shorts for black jeans. I do want to highlight these shorts which are the best denim shorts I’ve ever owned. They are cut a-line style which gives more room in the thighs.


tank (old from faherty (similar; similar) / skirt (similar; similar) / flip flops / sling bag (ASHLEYR15 for 15% off) / sunglasses / necklace (ASHLEYROHR10 for 10% off)

I don’t know if poplin skirts will still be in in the spring, but I’ll be wearing mine. I loved wearing this skirt last spring and found it to be a great alternative to my usual denim. My brown knit tank is old from Faherty but I found some similar options.


vest sold out from Sézane (very similar) / barrel jeans (size up in this wash) / mesh flats (similar) / bag (look for a restock soon) / sunglasses

I started wearing vests last spring, and it opened up some more outfits for me. Here, I’m wearing my black vest with barrel jeans and mesh ballet flats.


button down shirt / boxer shorts / bag (look for a restock soon) / sunglasses / watch / similar earrings / necklace

I wore these boxer shorts from Donni SO MUCH last spring and summer. They still look brand new, too – definitely worth the price (see some more styling ideas here!) For this look, which I’ll be repeating for sure, I wore them with an oversized white button down.


tank / linen pants (similar) / flip flops / bag (look for a restock soon) / sunglasses / similar necklace

The combination of a tank and lightweight pants is a spring go-to uniform. I’ll add a jacket when the weather is cooler.


tee (I go up two sizes ) / shorts (recommend going up a size) / mesh flats (similar) / sunglasses / necklace / bag (look for a restock)

Another simple look with a tee and tailored shorts (these are raw silk, and I love them so much I’m buying the black soon!) The mesh flats add a little more interest along with the texture from the bag and a bit of jewelry, too.


tee (I sized up) / suede jacket (size up) / barrel jeans (recommend sizing up in this wash) / flip flops / sling bag (ASHLEYR15 for 15% off) / sunglasses / necklace

I’m just waiting for the day I can wear this suede jacket again. It’s such an outfit maker. I’ve styled it here with a light weight tee (it’s pricey but so perfect!), barrel jeans, and flip flops.


linen shirt / linen shorts / leather flip flops / similar bag / sunglasses / similar earrings

This easy breezy look is just a matching linen set. It’s from Quince and super affordable. I do really like the contrast of the white outfit with the black accessories here.


I’m combining these two looks because they are the same top with black bottoms. This henley tank is from Sézane, and it has the best fit (great quality, too!) In this first look, I paired it with my silk pants from Na Nin (pricey, but they have such a unique shape you won’t find anywhere else; believe me, I looked!) In the second look, I’m wearing the tank with my black barrel jeans from Everlane (this wash runs true to size in my opinion).


vest sold out from Sézane (similar) / raw silk shorts (recommend sizing up) / similar sandals (mine are old dolce vita) / sunglasses / bag (look for a restock soon!)

Here’s another way I styled my black vest from Sézane for a warm spring day.


red tank (similar) / denim (similar) / flip flops / bag / sunglasses / similar necklace

I love the combination of red and brown for spring and summer. A few things in this look are older. This tank is from Sézane but sold out in red, and these jeans are also from Sézane but sold in this colorway. I found some similar options for you above.


striped top / pants / bag / similar sunglasses from same brand

Stripes are so quintessentially spring and that’s when I tend to wear them the most. This striped top is from Sézane and is very classic Parisian chic. I paired it with some wide leg brown bottoms from Everlane which are now sold out in this color.


tee (I went up two sizes ) / jacket / jeans / bag

You can bet I’ll be wearing some version of this outfit most days this spring. This jacket has a really cool wide fit in the body and sleeves. It feels a bit like a cropped trench coat. I’m wearing it with a white tee and baggy jeans.


cardigan (similar) / boxer shorts / similar sandals (mine are old dolce vita) / bag / sunglasses

Here’s another way I’ll be styling my boxer shorts for spring – with a button front cardigan or sweater. This cotton sweater is from Gap (keeping an eye out for a restock!) but I found a similar option for now.


linen button down / poplin skirt (similar; similar) slingback flats (similar) / bag (old clare v.; similar)

This look is so easy breezy but also trés chic, too. It felt weird to not tuck in my shirt here but I loved how the outfit turned out. It just appears more effortless this way.


tank (old from Faherty; similar; similar) / button down shirt / denim (size up) / flip flops / bag (look for a restock soon) / sunglasses

Here’s another way I like styling my button downs for spring – open with a tank underneath like a jacket. My button down is from Gap (my favorite lightweight button down shirt, I own it in way too many colors) and my jeans are from Sézane (always size up in Sézane bottoms).


tank / skirt (similar; similar) / fisherman sandals (similar) / bag (old from Clare v.; similar) / sunglasses

And finally, another version of the same look from above, I just swapped the tank for a beige one and the flip flops for fisherman sandals.


Read More:
Eight Outfits With White Jeans
Gray Sweater Outfits For Spring

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