How to Wear Ankle Boots with Leggings (Plus, the 2 Pairings You Should Skip)

You may assume that a tight-fitting boot paired with tight leggings is a great way to lengthen the look of your legs with one, long, seamless line. And you’re not totally off the mark. But it can also make you look oddly disproportionate, almost like an apple stuck on two popsicle sticks. You’re better off choosing a boot with a shaft that sits a little ways away from the ankle (it doesn’t need to be a dramatic flare, an inch is more than enough) to help define the shape of your leg and balance out your torso.

We’ve written before about loving the look of ankle boots without socks, but there are times when showing off your socks can actually be super cute (just ask Gen Z). Take, for example, hiking and combat boots, or really any lace-up style, with just an inch or two of tall socks sticking out from the top. Combined with leggings and finished with a cozy sweater or oversize coat, it gives off a supremely cozy vibe we can’t get enough of.

Slouchy fabric around the top of your boots is going to give off major ‘80s leg warmer vibes (and not in a good way). Plus, all that excess material can make petite frames or short legs look squat. The solution may be tucking your lengthy leggings into a pair of slightly taller boots, or it might be discreetly rolling the hem, so they fit just right. If you find yourself dealing with pooling fabric often, you should consider taking your leggings to a tailor to have them hemmed to just the right height, once and for all.

If you’re rocking a pair of zebra print, floral-embroidered or even bright red ankle boots, you likely want them to be the star of the show. The best way to give them space to shine? Stick to good old-fashioned black cotton leggings. On the flip side, if you recently picked up leggings with moto stitching or with an interesting print, keep your footwear sleek and simple.

This trick actually works for a number of fashion combos and is called Sandwich Dressing. The idea is to create a sartorial sandwich by balancing one piece on your bottom half with another on your top half and including something contrary in the middle. In this case, the sandwich is made by repeating the white shearling of the boots in the white stitching on the coat.

There’s an easy-to-remember rule when it comes to figuring out the right top to wear with ankle boots and leggings: high heels (3 inches and up) look better with a long shirt while low-heeled booties work best with shorter blouses. Why, you ask? It all comes down to proportions—a torso-elongating top or jacket balances out leg-lengthening heels, whereas a long sweater worn with flat booties might actually make your legs look shorter.

Sometimes, a busy schedule means finding ways to wear your workout ensemble for the rest of the day. Our tip for heading to brunch in this morning’s yoga pants and your cute new booties? Be sure to add a thigh-grazing knit into the mix. The sweater will help to bridge the gap between your structured ankle boots and your techy leggings, so you don’t look like you got dressed in the dark and accidentally pulled out the wrong legwear.

Black leggings and minimalist black booties will always look cool together, especially when worn with an oversize button-down or chunky knit…or both. Don’t be afraid to resort to the tried-and true if you’re strapped for more out-of-the-box ideas. There’s a reason these looks are considered classics.

Look, we’ve all had weeks where the laundry probably should have been handled ages ago and we’re forced to get a little creative with the items still in our drawers, but trust us when we say capris and ankle boots do not mix. You’re much better off covering up your calf with some knee-high or over-the-knee boots. (Or, you know, finally doing laundry.)

It can be mighty tempting to slip on those fleece-lined leggings between a skirt or dress and cute booties mid-winter, but we’re not particularly big fans of this combination. Realistically, wearing your leggings as tights all too often ends up looking bulky, especially at your middle where the waistbands layer atop one another. Not to mention, they can add extra heft to your legs when paired with boots. Lucky for dress-lovers, there are plenty of fleece-lined tights available for a look that’s just as warm and all the more streamlined and flattering.