Figuring out what to wear with leggings, one of the most polarizing pieces in fashion history, has become a key part of the millennial existence. If you’re over the age of 30, the athleisure staple has likely carried you through every major milestone of your life. Even as your tastes changed, your best leggings remained a constant.
During high school, we wore flared versions (a.k.a. yoga pants) with North Face jackets and Ugg boots. Then we traded those for ankle-hugging styles that showed off our booties; these became the norm so quickly they even surpassed the omnipresent skinny jeans. In adulthood, the critical eyes of Gen Z made us briefly question this lifelong allegiance to the wardrobe staple. But then quarantine hit, and suddenly leggings were the most-worn item in our collective closets once more.
And now, in 2026, we’re much better at styling leggings. With the rise of microtrends like corporate sleaze, quiet luxury, and European summer, today’s leggings are being worn in chicer ways than they ever have before. In fact, they’re so stylish, I’d dare say even Gen Z would approve. Ahead, read on for insider-approved outfit formulas and style tips for what to wear with leggings to be on trend for 2026.
French Girl Corpcore
The last few fashion seasons have played host to a plethora of minimalist business-casual staples that absolutely demand to be worn with a comfy pair of leggings. Fitted blazers, specifically, offer the perfect amount of structure to offset these skintight bottoms. Dress up the look even more with a pair of slinky pumps or kitten heels for a classy take on the ’90s secretary look for date night or the office.
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Toned-Down Trench Coat
The easiest way to make a Saturday morning ’fit look put-together is by popping on a trench coat. And instead of white sneakers, try pair of posh shoes like ballet flats or loafers. This simple addition can make any piece of loungewear feel less “couch rot” and more “cool city girly.” This rule applies to your standard black leggings, of course, but it also works with hoodies, oversized T-shirts, and baggy track pants. Running errands has never looked so chic.
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Pantaboots
Pantaboots have been a running joke since they first debuted in 2022—and honestly, fair. But when done well with, say, a crisp blazer, button-up, and necktie, the legging-footwear hybrid comes out looking surprisingly elevated. You don’t have to actually invest in a pair to pull off this look, either. Just style your best Alo leggings with a pair of sock boots for a quick-and-easy dupe.
’80s Influence
Yep, stirrup leggings are back. And if you’re looking for ways to style your own, I’d recommend outfit ideas that involve reaching for other fashion trends from the same era. Gloves, pumps, and an oversized furry, leather, or suede jacket (this winter’s biggest outerwear trend) will underscore their retro nature while still retaining a modern feel. In fact, this outfit idea also applies to all your favorite leggings, stirrup or not.
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Edgy Layers
This look is truly a testament to the versatile nature of a good pair of leggings. If you’re looking for a more daring leggings outfit, consider a mash-up of funky layers. Double down on belts, slip on a pleated skirt, and finish with a sporty zip-up sweatshirt for a playful, Miu Miu-inspired ’fit.
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Luxe Faux Fur
If this winter has taught us anything, it’s that an expensive-looking faux-fur coat or vest can make virtually anything feel stylish and cutting-edge—even your most battered pair of Lululemon tights. Add more French-girl favorites (like a stretchy headband from Amazon, a crewneck top, and knee-high boots) for a leggings-forward look that feels shockingly posh.
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Mocha Cream
Brown has been the trendiest color of 2025, with no signs of slowing down in 2026. Instead of an edgy all-black look, consider trying a slightly softer approach with a chocolate color scheme. Wear leggings in a deep brown with matching riding boots for a streamlined approach. A thick cardigan or blazer layered with a long-sleeve cream blouse is a sophisticated combo, or go with a belted oversized sweater or sweaterdress.
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Icy Sophistication
For a polished evening leggings look that’ll still keep you warm, layering a gray or icy blue pair with a dressy skirt and long wool coat is a cool-girl way to handle the cold weather. Don’t forget the sparkly jewels or fancy heels, of course, to keep this ensemble looking elevated and on point.
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