5 Ways to Wear Leggings In 2026—and 2 That Feel Dated

This look is all about balancing your proportions, with the volume of the sweatshirt and chunkiness of the dad sneaker offsetting the slim fit of the leggings. However, a lengthier coat (whether a wool one or trench) is key, as it adds a long line that ties it all together. Sporty meets sophisticated—and the perfect option for going from the gym to brunch on a Saturday morning.

I’ve been seeing tons of fashion girls style their leggings with laid-back layers and shoes that supply a dash of polish. Start with a white tee or button-down, throw on a relaxed crew- or V-neck knit and slip into some loafers—preferably, with some thick socks that cover your ankles. I love this fit for spring, as you can take off the sweater and drape it over your shoulders if it gets too warm (or do the reverse if you catch a chill in the air). Options, people.

Rather than sandwiching your sleek stems between two chunkier silhouettes, this approach seeks to play up the slim fit through your legs while adding a boxy contrast up top. You’ll want to stick to a boot that’s the same color as your leggings (black-on-black preferred) in order to create an elongated, monochrome look on your bottom half. Here I’m wearing my favorite wool scarf coat from Quince, but you can also try it with a boxy quilted jacket or bomber.

Think you can’t wear a short top with leggings? Think again. Don a cropped, fitted cardigan as your top (buttoned up, of course), and tie a thin, long-sleeve sweater or shirt around your hips. It feels effortless in the best way and gives your casual look some visual interest. For an athleisure vibe, pair it with low-profile sneakers and a baseball cap for good measure.

For an outfit formula that never misses, you can’t go wrong with a simple black turtleneck and oversized blazer. You can get away with dramatic shape and structure up top when your base layer is slim and minimalist, so the bigger the shoulder pads, the better. I like to keep the line looking streamlined with pointed-toe knee-high boots, but in warmer weather, try swapping them out for black slingbacks to achieve a look that’s just as chic.

If you want to avoid looking like your throwback pics from 2016, skip the ankle boots—particularly if they leave room between the collar and the hem of your leggings. That sliver of sock or skin in between breaks up the length of your leg, and it appears disjointed rather than sleek.

I have worn my fair share of sweater dresses with leggings over the years, but in 2026 leggings are pants—so don’t treat them like they’re tights. Paired with a longer hemline and thicker material, leggings can feel a little dowdy. Swap ‘em out for sheer stockings or even a bold-colored tight to take your sweater dress into today.