5 Flare Leggings Outfit Ideas That Are Equal Parts Comfy and Chic

It ever you’re unsure how to style a particular bottom, be it some linen shorts, an A-line midi or flare leggings, you simply can’t go wrong with a plain white t-shirt. In this case, a fitted style will complement the curve-hugging fit of your pants nicely, to give you a sleek silhouette from head to toe. Finish with some low-profile sneakers and consider adding an oversize jacket on top to strike a fun balance between slim and big.

If slim-on-slim isn’t you jam, try a boxy cropped tee instead. The key here is to choose something that hits just above your hip bones to keep your proportions in check. Too cropped, and you’ll look like you’re borrowing from your Gen Alpha niece. Too long and you run the risk of looking schlubby or like you left the house in your PJs. A boxy cut is every bit as comfortable as your giant sleep tee, but will ultimately look far more polished, especially if you finish the ‘fit with a retro sneaker and sleek leather crossbody bag.

I love playing with the idea that opposites attract, and it works really well with flare leggings, too. A tailored button-up shirt can actually help elevate the athleisure vibes of your bottoms to make the whole outfit feel more posh. One piece of advice, however: Look for button-ups that are more casual than crisp. An oversize silhouette, linen fabric or pale pop of color will make a lot more sense with leggings than a starched, white shirt better suited for, well, a suit.

In the same way that a boxy cropped tee looks more put together than an oversize one, a sweatshirt that hits just above your hips will ultimately feel more polished than a giant hoodie when worn with flare leggings. Whether you prefer a half-zip, full-zip, crewneck or hooded style is entirely up to you. Just make sure it has at least a little slouch to balance the flare of your pants with some volume up top.

My secret “all purpose” top to pair with just about anything and everything in your wardrobe? A striped crewneck sweater. White-and-navy or black-and-white versions are obviously the most versatile, but don’t let that stop you from rocking alternatives if the classics aren’t your thing. Because these Breton stripes give major French-woman vibes, there’s an inherent sense of elevated style that other solid-colored pieces just don’t have. As a result, you can toss just about any striped crewneck on over your flare leggings and find it looks pretty darn chic.