The Best and Worst Ways to Wear Leggings in 2020

Some might argue that leggings should not be worn in place of actual pants, but we say comfort is king and until pants are as easy, comfortable and sleek as classic black leggings, we’re going to wear ours anywhere we please. That said, there is a right way to wear your stretchy bottoms, because there are some top and legging combos that are less flattering or fashionable than others. Here are four styles to avoid, plus three to wear in their stead.

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woman wearing a tight cropped blazer and leggings
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Worst: A Slim-fit Or Cropped Blazer

We’re going to give you the most important piece of styling advice right up top: Balance is key. A tight blazer with tight leggings ends up looking like you tried to make a catsuit into something more office apropos. And yes, a cropped length only exacerbates the problem.

woman wearing an oversize blazer and leggings
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Best: An Oversize Blazer

You know what kind of blazer does work? A posh, oversize one, preferably with a slightly longer hemline that hits mid-thigh. The additional length and looser fit offer a welcome counter to skin-tight leggings and can actually make your legs look slimmer in comparison. One note of caution: Don’t go too boxy or baggy or you’ll look like a kid playing dress-up.

Get the look: Superdown ($68); Halogen ($72); Majorelle ($78); Endless Rose ($105); 1.State ($169)

woman wearing a tight tunic and leggings
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Worst: A Tight Tunic

Remember, opposites attract, especially in fashion. Rather than show off your great figure, this combination only serves to make you look like you’ve got particularly odd taste in workout gear.

woman wearing a mini dress with leggings
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Worst: A Minidress

You may think leggings and tights are interchangeable but that’s not quite the case. Because leggings are thicker and often more matte than a pair of tights, they give the illusion that you’re just wearing pants under your dress. This ends up feeling particularly odd if you also throw on a pair of flats, sneakers or another ankle-baring shoe. It can also cause others to wonder why you’re wearing all your clothing at once.

woman wearing a sloose tunic top and leggings
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Best: A Loose Tunic

The tunic’s intrigue lies in the fact that it’s a bit too long to function as a regular top but too short to be worn as a dress. However, these are also the qualities that make a tunic the right thing to pair with leggings (which are too thick to be tights and too thin to really be pants). Opt for a style with a relaxed silhouette that hits just below your crotch to achieve a perfect balance.

Get the look: All In Favor ($25); Caslon ($35); Free People ($38); Maaji ($86); Eileen Fisher ($108); Lovers + Friends ($155)

woman wearing a crop top and leggings
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Worst: A Crop Top

You can have the most impressive abs of all time, but a crop top with leggings still isn’t the way to go (unless, of course, you’re headed to the gym). Leggings are great for making your legs appear supermodel long, but when you top it off with a tiny tank, you shrink your upper half to a comical degree, especially if your leggings are high-waisted.

woman wearing a chunky sweater and leggings
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Best: A Chunky Sweater

There’s a reason this is one of the greatest fall and winter outfit combos of all time. Besides being delightfully comfy and cozy, an oversize sweater also helps to mask any lumps or bumps you might want to hide. Black leggings do their part to smooth and lengthen your legs, so by combining the flattering superpowers of both, we end up with an ensemble that’s 100 percent fabulous.

Get the look: BP. ($59); RACHEL Rachel Roy ($62); Topshop ($68); Free People ($148); Zella ($149); Brochu Walker ($368)

Still on the hunt for a go-to pair of leggings? Check out some of our faves below.

Get the look: BP. ($19); Hue ($31); Coldesina ($42); Vince Camuto ($59); Spanx ($68); Zella ($69); Commando ($98)



Abby Hepworth is an RRCA-certified running coach who has worked in fashion for over 10 years. Want to know what shoes are in this season? She's got you. Need recommendations on...