Style Leggings With These 10 Finds, According to Pros

Leggings have been a closet staple for years, but sometimes leggings can date an outfit—and not in a good way. If leggings are your comfy pants of choice, we asked three professional stylists how to make sure your legging outfits stay modern and stylish. 

Celebrity stylist Kim Appelt, 24-year fashion industry veteran Sharon Warten, and Evoluer Image Consultants founder Cheryl Ann Wadlington told REAL SIMPLE that leggings should be paired with at least one polished piece. So here are some sweaters, blazers, coats, and flats to make your leggings look fashion forward.

Stylist-Recommended Legging Fashion Staples

Flare Leggings

A skinny silhouette can make leggings feel dated, so Appelt recommends flare leggings instead. This pair comes in four inseams to accommodate a wide range of heights. “They instantly feel more polished than a tight ankle legging,” explains Appelt. “They balance the body perfectly. They’re especially great for women with curves or athletic thighs because the flare balances the hip and creates a longer line.” 

Oversized Blazer

One easy way to make leggings look trendy is to pair them with an oversized blazer. “Pair a black flare legging with a slightly oversized blazer and a simple fitted tank or tee,” suggests Appelt, who treats leggings like a foundation piece rather than the centerpiece of an outfit. “Finish with a clean sneaker or a ballet flat. It’s comfortable but still pulled together.”

Relaxed, Oversized Cardigan

“A simple rule I tell clients is leggings look best with at least one ‘real clothes’ piece,” says Warten. “That little bit of structure makes the whole outfit feel styled.” She suggests a relaxed or oversized cardigan, like this mockneck style, to minimize the “gym” look that was so popular with leggings in the past.

Oversized Button-Down Shirt

Pair ponte-style leggings with a relaxed button-down shirt if you want a casual look that isn’t frumpy. Appelt recommends half-tucking this oversized shirt into your leggings for a perfect spring-ready leggings ensemble. “The trick is simply updating the proportions,” she says. “Think longer layers, slightly looser tops, and fabrics that feel more elevated. When the balance is right, leggings can look incredibly chic.”

Denim Jacket

“Not only are leggings versatile and comfortable, but they are also super transitional,” says Wadlington, who recommends wearing leggings with a denim jacket and tunic for a timeless, layered spring look. Since denim is so versatile, you can have a little fun by combining it with printed leggings rather than a safe, solid black color.

Alternative-Fabric Leggings

If your leggings look like they’re stuck in the 2010s, it could be the material that they’re made of. “Fabric matters, too,” says Warten. “Ponte, or faux-leather leggings, instantly look more elevated than basic cotton.” These pull-on ponte leggings come in flare, slim, or straight, so you can pick the silhouette that best suits your frame.

Structured Outerwear

Oversized Sweater

When it comes to leggings, you can always count on an oversized sweater to create a timeless look. “I always say leggings need a partner piece—a longer blazer, trench, or oversized sweater creates balance and makes the outfit feel intentional,” says Appelt. This relaxed turtleneck offers coverage and clean lines to make leggings look more polished—perfect for cool mornings and evenings as spring arrives.

Flat Shoes

Don’t underestimate the power of a perfect shoe to turn leggings from frumpy to fashion forward. “I always advise my clients to choose clean sneakers, ballet flats, loafers, or knee boots to keep the look modern,” says Warten. These classy ballet flats have a round toe and leather design that are ideal for spring and beyond.

Penny Loafers

Appelt recommends loafers to instantly elevate classic black leggings, especially if you’re wearing a relaxed sweater or button-down shirt on top. She likes these loafers for the soft, collapsible heel, making them easy to slip on and off. The moc toe is also a nice touch to add some interest to a casual look.