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May is here, which means it’s time for warm, sunny days, fun-filled activities to kick off summer, and all the colorful, breezy, well-coordinated outfits to match. The trends are already full of soft palettes of pastel pink, periwinkle, and butter yellow, while tennis-inspired aesthetics from Zendaya and Serena Williams are inspiring major love, both on and off the court. Wrap that all up with a pink satin bow—as Kacey Musgraves has quite literally done this season—and you’ve got a closet primed for spring-to-summer transitional dressing. Keep reading to discover 13 outfit ideas for May, complete with product picks to get the look for yourself.
Equestrian Ensemble
Graphic tees are having a moment—and this sweet version from Tyler McGillivary also takes the concurrent modern cowgirl trend to heart. Try pairing a bold equestrian tank with on-theme accessories and an easygoing pair of denim shorts.
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Tyler McGillivary
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Kristin Ess
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Wrangler
Short and Sweet
Warm-weather errands call for something a bit more breezy than your typical athleisure look. This ensemble combines lightweight shorts with a fluttery top, proving that maintaining style and comfort during scorching humidity doesn't have to be hard.
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Free People
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Fila
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Jeffrey Campbell
Skirting the Rules
While you may not have imagined a pleated skirt fitting into your summer wardrobe, this festival look from Barbie Ferreira asks you to reconsider. She isn’t alone in her take on summery attire—if we learned anything from this year’s Coachella outfits, it’s that you can never go wrong with a mini skirt and statement belt.
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Good American
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Mango
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Levi’s
Picnic Elegance
You caught us daydreaming, much like Kacey Musgraves does here. The Deeper Well singer's dreamy look evokes visions of cottages and fairytales—and these pastel florals fit right in. Dramatic silhouettes also make an appearance via an oversized satin bow and wide-brimmed hat.
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& Other Stories
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Alice + Olivia
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J. Crew
Beachside Buttons
This ensemble could easily fit into any given episode of The White Lotus. Whether you’re catching an international flight or simply browsing your vacation options, this straightforward resort-ready dress neatly reimagines the quiet luxury aesthetic in a streamlined, ’60s-inspired cut that feels adjacent to the current Palm Beach chic trend.
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Reformation
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Steve Madden
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Boden
Game, Set, Match
There’s an art to combining athleisure with dressier pieces, but rest assured that our spring cover star, Serena Williams, is a pro at striking this balance. Pair a sweet, floral midi skirt with a practical pair of sneakers and a weather-ready jacket, and you’ll be poised for whatever the day might bring.
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Good American
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Camila Coelho
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Athleta
Getting Geometric
Your new bikini and coordinating coverup deserve more time in the sun—and in your daily wardrobe, too. Try pairing a matching set with a standard pair of wide-leg jeans and pointed toe boots for an intriguing yet entirely wearable hint of contrast.
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Riot Swim
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Frankies Bikinis
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Madewell
Breezy Basics
Lightweight sets are already a staple in our wardrobes, so consider this fun, retro-inspired take on monochrome to be your unofficial summer uniform. These on-trend studded clogs are a no-brainer when paired with playful red sunnies.
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Good American
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Coco and Breezy
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Everlane
Slip Into Summer
We’re willing to bet that you’ve already scrolled past a dozen micro-mini slips in your social feed. Here, Hailey Bieber contrasts a sweet, lace-lined satin piece with tougher leather boots and a bedazzled pendant necklace.
Product Picks
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Homebodii
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BaubleBar
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Zou Xou
Bringing May Flowers
Vintage-inspired blouses are on the rise this summer, and the floral details on Anthropologie’s version capture the same ethereal essence of Laufey’s Miu Miu piece—albeit at a far more accessible price point. Follow suit with a delicate string of dangling pearl earrings and a darling wrap skirt.
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By Anthropologie
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Kimchi Blue
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Chan Luu
Daring Denim
Outdoor adventures ahead: We’re earmarking sensible denim sets for every fresh-air occasion—from hikes to park hangouts and even drinks al fresco (it counts, too). Depending on the temperature in your locale, you can easily swap this jacket for a coordinating denim vest.
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Rag & Bone
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Madewell
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Oma the Label
Structured Sundress
This structured silhouette lives rent-free in our minds (and our online shopping carts). Drop-waist and corset bodice dresses are especially on-trend right now, as brands add a decidedly elegant twist to an otherwise standard summer staple. A contrasting red handbag stands as the cherry on top.
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House of CB
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Brandon Blackwood
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Dolce Vita
Sunny Style
Sunny days call for equally vibrant palettes, and this look from Ashley Graham certainly doesn’t fall short. Don’t shy away from pairing rich botanical tones, like sage green and bright yellow, for an eye-catching look primed for weekend brunch plans in May and beyond.
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Gap
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Old Navy
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Tony Bianco