It seems every week, we’re here to chat about what to wear (and not wear) with leggings. We’re hoping this is helpful information since you probably live in the stretchy pants as much as we do and, as a result, are consistently on the hunt for forward, new outfits to wear with them. Since all A+ ensembles start with the perfect shoes, we’re going to go over the footwear style we’re not really seeing fashion people wear with leggings—and what they’re wearing instead.
While you can absolutely dress up leggings if you desire, they are inherently casual in nature and lend themselves well to more toned-down pairings. To that, the fashion crowd seems to be getting over wearing formal, pointed ankle boots with leggings in favor of silhouettes like combat boots. This makes perfect sense. Because really, if you’re wearing leggings, chances are the goal is to stay comfortable and cool off-duty, and high-heel booties wouldn’t necessarily accomplish that.
With that in mind, keep scrolling to find outfit inspiration of fashion girls wearing the boot style of the moment with leggings, and shop each look too.
For an on-trend look, pair your leggings and combat boots with a furry coat and a belt bag.
This 'fit works better if it's not completely frigid where you live with the crop top, longline coat, leggings, and boots.
A layered look instantly feels forward and cool. Follow this style setter's lead with a skirt over your leggings, complete with your boots, a jacket, and a scarf.
If you do want somewhat of a heel, go for a pair of boots in between a combat style and booties with your leggings, a dress, and a coat for a streamlined ensemble.
Hey, there. Bobby here. I've been working as a fashion writer in the industry for over a decade, contributing to various websites and brands such as Refinery29, Men's Health, and of course, Who What Wear. I've spent many years at Who What Wear, currently acting as the senior market editor where I source the coolest and chicest items at our favorite stores to help you, dear readers, build your version of the perfect wardrobe. While I lived in NYC and L.A. for a while, I actually now live in Boston. Sure, I've changed locations, but my fashion perspective remains the same, as I tend to reach for those classic basics with a twist (think slouchy moto jackets, trendy joggers, and the like). When I'm not writing or talking about fashion, you can often find me catching up on my favorite Bravo shows (Vanderpump Rules and The Real Houswives of New York City are my favorites) or sipping my signature cocktail—a vodka martini with a splash of cranberry and a twist.
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