The revival of windbreaker shorts was not on my 2026 bingo card, but alas, they’ve become a pillar of athleisure. First popularized in the ’80s and ’90s, the lightweight, swishy bottoms were known for bold, color-blocked designs reserved for the gym. Still, it wasn’t long before style icons like the Sex and the City character Carrie Bradshaw pushed the boundaries, wearing the silhouette with kitten heels and a crop top.
A similar reinvention is unfolding now, with It girls putting a fashion-forward spin on the nostalgic briefs, which take their name from their jacket counterpart. Oversized T-shirts, designer handbags, sculpting corsets, and sleek flats are becoming a natural extension of sprinter shorts — and while you’re bound to spot an abundance of hot pants in the park, you'll also start finding them on city streets, in airports, and potentially at a casual happy hour.
It’s all about knowing how to style the retro shell cutoffs. For an undeniably casual look, reach for a simple tee, crew socks, and sneakers. It delivers an unfussy gym-to-street look that may just be the easiest entry point into the trend. If you're aiming for a more elevated aesthetic, contrast is key. Slip into a slinky lace tank and add a structured layer, like an asymmetrical blazer or cinched trench coat. The interplay between sporty nylon and chic tailoring is where the magic happens.
Unexpected footwear is yet another clever style direction. The shorts feel more intentional when paired with minimalist sandals, ballet flats, and pumps. It’s a simple way to upgrade the piece without overthinking the entire look — turning a sporty staple into a fashion-forward moment.
If you’re craving nostalgia and ready to give windbreaker shorts a try, keep reading for 15 elevated picks.
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I own these exact shorts in blue and wear them everywhere, from cafes to the park. But the candy-red stripes and bubblegum-pink colorway might just be enough to convince me to grab a second pair.
edikted Nikki Side Stripe Nylon Shorts, $, available at Nordstrom
These feather-light bottoms offer maximum airflow, paired with built-in coverage so you always feel secure. Side zip pockets and a drawstring detail offer versatility for on-the-go moments.
Lululemon Track That High-Rise Lined Short 3", $, available at Lululemon
From the hidden drawstring waist to the vibrant side stripes, these playful cutoffs fully lean into the retro aesthetic. Look forward to stretchy satin that feels soft and smooth against the skin.
Aritzia Curva Dolphin Short, $, available at Aritzia
A juicy grapefruit-and-tangerine color combo brings an instant energy boost, while the easy pull-on design makes these shorts a warm-weather staple.
Revolve x FP Movement Now Or Never Short, $, available at Revolve
More refined than previous styles, these boat-ready bottoms are made for mules and sun hats alike. Dress them up or down with breezy linen shirts and simple tank tops.
J.Crew Cruise Drawstring Short, $, available at J.Crew
Handle the unexpected with weatherproof shorts. No matter the forecast, you’ll have a pair of trending eggplant-colored briefs at your fingertips.
Nike Water Repellent Running Shorts, $, available at Nordstrom
Made for adventure, these durable shorts keep things practical and polished thanks to breathable fabric and functional pockets. They’re an easy choice for everything from coffee runs to mountain hikes.
Quince Micro Ripstop Mid-Rise Hike Shorts, $, available at Quince
Feel free in these stretchy hot pants that fight odors, keeping you fresh for longer. The deep indigo hue is simple to style with gray hoodies, white sneakers, and tan hats.
Rhone Lightspeed Performance Shorts, $, available at Nordstrom
Bold piping adds a sporty twist to this timeless pull-on style, while the water-resistant fabric makes them perfect for surprise rain showers.
FP Movement Varsity Blues Shorts, $, available at Free People
It doesn’t get more Y2K than a pink-and-brown color scheme. Pair these low-effort minis with a tube top and trainers for an effortlessly undone look.
Old Navy High-Waisted TrekTech Run Shorts, $, available at Old Navy
A true wear-everywhere find, these black shorts are the definition of easy dressing. The quick-dry fabric makes them ideal for everything from quick workouts to midday errands, while the subtle sporty cut keeps them sleek and flattering.
Vuori Clementine 2.0 Performance Shorts, $, available at Nordstrom
While inherently sporty, these pink minis are so sweet, they might as well be styled with thong kitten heels and a tiny shoulder bag for a playful, off-duty twist.
Nike Dri-FIT Mid-Rise 3-Inch Brief-Lined Shorts, $, available at Nordstrom
The electric lime-green hue makes a statement, while the micro curved micro hemline gives you legs for days. They’re so lightweight, you’ll barely notice you’re wearing them.
Aerie OFFLINE By Aerie 2" Hot Stuff Short, $, available at Aerie
Like what you see? How about some more R29 goodness, right here?
Every Cool Girl Is Wearing These Shorts
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