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

If the shaft of your boot barely hits your ankle, then its best to let that bare skin show. Wearing an extra-long pair of leggings or tall socks with such a low-cut shoe throws off your proportions in an unflattering manner. But letting your ankle go bare, in this case, can actually make your legs look long and lean

Shop similar styles: Nordstrom leggings ($59); Commando leggings ($98; $58); NBD leggings ($168); Style & Co. boots ($80; $56); Michael Michael Kors boots ($175; $132); Vince Camuto boots ($150)

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. 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 topped off with a cozy sweater or oversized coat, it gives off a supremely autumnal vibe and evokes images of apple-picking day trips and leaf-peeping car rides.

Shop similar styles: BP. leggings ($12); Zella leggings ($59); LNA leggings ($125); Bombas socks ($15); Hue socks ($18); Nordstrom socks ($19); Sam Edelman boots ($150); Dr. Martens boots ($150); Blondo boots ($180)

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 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.

Shop similar styles: Halogen Petite leggings ($49); Wit & Wisdom Petite leggings ($68); Spanx Petite leggings ($98)

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.

Shop similar styles: Hue leggings ($36); Lands’ End leggings ($40; $23); Splendid leggings ($58); MIA boots ($70; $49); Naturlizer boots ($100); Charles by Charles David boots ($130; $112)

Making printed leggings work with ankle boots is tricky business, but it absolutely can be done. Try to stick to classic black or dark brown footwear, to give your funky leggings a solid base. Then, add a textured knit in a complementary color up top. It doesn’t need to be an exact match (the above gray sweater works well with that black-and-white pattern), so long as it has a visible texture of its own, to balance out the busy nature of your pants.

Shop similar styles: Vero Moda sweater ($59); L.L.Bean sweater ($60); French Connection sweater ($128); Zella leggings ($65; $39); Spanx leggings ($68); Electric Yoga leggings ($72); Franco Sarto boots ($149; $105); Michael Michael Kors boots ($200; $150); Vince boots ($395)

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.

Shop similar styles: Halogen blazer ($140; $94); Treasure & Bond blazer ($99); Anine Bing blazer ($349; $210); American Eagle Outfitters leggings ($35; $27); BB Dakota leggings ($58); Blank NYC leggings ($98); Linea Paolo boots ($140); Madewell boots ($188); Schutz boots ($290)

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.

Shop similar styles: A New Day sweater ($25); Free People sweater ($168); Cotton Citizen sweater ($225); Lilybod leggings ($88); Summersalt leggings ($95); All Access leggings ($98); Bella Vita boots ($110; $77); Linea Paolo boots ($170); Kork-Ease boots ($190)

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.

Shop similar styles: H&M sweater ($40); Zella sweater ($149; $90); Naadam sweater ($215); Maidenform leggings ($63); Cuyana leggings ($75); Alo leggings ($114); Dolce Vita boots ($120); Vionic boots ($170); Marc Fisher Ltd. boots ($100);

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.