Can you hear that? It’s summer calling and she’s ready for you to be outside. May has officially made it’s way here, and after what has felt like a never-ending tug-and-pull between winter and spring weather, we’re finally getting some true-blue warmer days back-to-back. Which means it’s time to make plans with everyone you know and show off the outfit inspiration you’ve been saving to your Pinterest boards.

Now, while the days are starting to get warmer, we can still expect a small breeze at night, so it’s important to make summer layering apart of your sartorial vocabulary. A light sweater and button-down shirts will be your best friend this month. But more than anything, when it comes to our burgeoning warmer weather fashion, we’re going to be unafraid of tackling those eccentric trends, like neon and print-mixing. Let’s make them feel not only dynamic, but intentional and custom to you.

Take a look at the below combos for the inspiration you need to step into warmer weather with the chicest ‘fit possible.

Moss-Green Skirt With a Pop of Animal Print

Street Style - September 2025 New York Fashion Week
Edward Berthelot//Getty Images

This is a quintessential May outfit, especially for those working girls. This matcha green mid-length skirt with leopard print kitten heels is a fun way to be bold with your fashion. Pairing it with a muted gray, loose-fitted collared shirt is perfect. And adding in that striped shirt tied around the waist is a perfect layering trick.

Crochet Skirt With a Tank and Peekaboo Bralette

Street Style - September 2025 New York Fashion Week
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For the hot gyals with Rihanna on their mood boards, leaning into a crochet moment (no matter the location) is the best way to ellicit those summer vacation vibes even before you get on the plane. Using a multi-colored crochet skirt as the centerpiece of your look with a basic colored tank top and peekaboo bralette is a fun outfit choice for May that shows a little personality and flare.

Sheer, Head to Toe

They Are Wearing:  New York RTW Spring 2026
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You cannot go wrong with a flowy coordinated top and bottom. These sheer, white balloon pants paired with a matching spaghetti strap top with lace trim is the perfect beginning of summer look. Adding in the mesh ballet flats to complete the full see-through-esque moment is something I plan to recreate before Labor Day!

Button-Up With a Sporty Short

They Are Wearing:  New York RTW Spring 2026
WWD//Getty Images

Now I know you’re probably thinking: Why would I pair a button-up shirt with athletic shorts, but hear me out. It is actually a fun way to mix-and-match without it feeling overwhelming. This loose-fitted long-sleeved dress shirt paired with white shorts, yellow thong kitten heels, and a light blue sweater across the shoulders (for vibes) is such a fun summer look. It feels elevated, but fun. Accidental, yet purposeful. It’s not trying too hard, but it still feels calculated. I, for one, plan to style a few looks this May with this combo.

A Gingham Micro Shorts Set

Street Style At Copenhagen Fashion Week SS26 - Day 3
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You cannot call it summer without gingham and this matching set moment is a prime look. When struggling to put together an outfit, the easiest thing to do is grab-and-go a fun set. Especially one like this. Micro shorts are all the rage right now, so stepping out in a pair let’s everyone know you’re tapped into the hottest trends.

Maximalism on Top, Sporty on Bottom

They Are Wearing:  New York RTW Spring 2026
WWD//Getty Images

You know these girls. When you see them walking down the street you think, “Wow she looks cool.” I know I do, at least. Maximalism is all the rage and this is a fun way to tap into that without looking too extreme (if you’re a newbie and just starting to explore). A fun and edgy track pant like this one paired with a multi-layering moment, like this printed bandeau top, sheer black shirt, and neon pink bra is a cool-girl way to wade into the waters.

Layered Skirts With Satin Staples

Street Style - September 2025 New York Fashion Week
Christian Vierig//Getty Images

Everyone could use a little sparkle in their life and this tonal moment is the perfect way to incorporate it for summer. Pairing a little skirt layering moment with a satin set is a fashion moment we all should be tapping into now that the weather is warming up.

A Linen Set Moment With Western Flair

Street Style - New York Fashion Week September 2019 - Day 1
Daniel Zuchnik//Getty Images

You cannot go wrong with linen during the summer months, so you might as well kick off the warmer weather with full commitment in a set. A loose-fitting button-up shirt with frilly matching shorts (and a good boot) is the way to go.

Mixing and Matching Preppy Plaids

Street Style - September 2025 New York Fashion Week
Jeremy Moeller//Getty Images

Now, I for one believe in the collegiate aesthetic all year-round. But getting a jump start on fall’s favorite print with a full plaid look in May might be just what needs to happen. Paired with a fun bag and Mary Janes, this look scratches the preppy itch nicely.

Cropped Tee With Baggy Pants and a Pop of Color

Street Style - September 2025 New York Fashion Week
Edward Berthelot//Getty Images

Sometimes, life can get a little hectic. And you don’t want to think about your outfit. So, when in doubt, the classic model-off-duty look (jeans and a tight tee being the uniform) is your go-to. A nice pair of jeans with a white top is easy enough, with most people owning these staples. Now if you want to make the look more fun, you can make that white shirt cropped and lean even deeper into a boyfriend or baggy jean moment, like Ella Emhoff here. Add a bright colored sweater around the waist, and you have a fashion look!

Lettermark
Aiyana Ishmael
Style Editor

Aiyana Ishmael is the style editor at Cosmopolitan magazine. In her work, Aiyana focuses on the culture of fashion and how it intertwines and shapes the zeitgeist. She is an award-winning journalist from Miami, Florida, and a graduate of the historically Black university, Florida A&M. She is a 2024 Forbes 30 Under 30: Media honoree, and her debut romance novella PASSING GAME is set to release March of 2027 (831 Stories/Simon & Schuster).