The Best Shoes to Wear With Leggings

Leggings are super-comfortable, and they can be worn with a variety of pieces, like long sweaters in the fall and winter, and thin tunics in the spring and summer. They also work well when worn as tights with short skirts and dresses. They do have their critics, though, and like most clothing items, some ways to wear them are definitely better than others. A big part of making leggings work for you is choosing the right shoes and boots to wear with them. It's not difficult and, fortunately, choices abound.

Ballerinas and Other Flat Shoes

Actress Katie Holmes, pictured wearing black ballet flats with black leggings.
Photo by Ray Tamarra / Getty Images

Ballerina flats are a perennial favorite to pair with leggings. It's no wonder: They have their slim, streamlined looks in common. 

The low cut of ballerina flats means that the tops of your feet will still be exposed. This is a good thing because it creates a visual break between the shoes and the leggings, but neither item overpowers the other. Plus, that little wedge of skin calls attention to the style both above and below it.

As a general rule of thumb, go with ballet flats that are the same color or darker than your leggings—or, if you want a slightly dressier look, try a pair of metallic ballerina flats. Silver will work with just about anything, but earth tones and golden metallics really rock here. For a little less flash, opt for a matte ballerina flat with just a hint of shimmer.

In addition to ballet styles, other flat dress shoes such as pointy-toed, slingback, open-toed, and smoking flats (like those pictured here) generally work well with leggings. Remember, though: Low-cut styles that leave some foot skin showing are best.

In spring and summer, you also can pair long leggings with flat, thong sandals; those with really skimpy, delicate straps work best.

Here are a few great choices in flats and sandals: 

Perfect Combo: Leggings With Boots

Tall, cognac boots with simple, classic styling and full side zippers.
Steve Madden 'Shawny' Image:

Even though leggings work well with boots of nearly any height, they look especially great with tall boots.

One of the reasons this is a winning combination is that, when paired with mid-calf or knee-high boots, leggings almost begin to look like tights, but much more substantial and opaque. Another reason it works: Tall boots cover your calves and help combat the leg-thickening effect that leggings sometimes have.

For a fun, casual look, try wearing leggings with tall, flat, lace-up, combat, slouchy, or riding boots.

If you want a look that's a little more polished, opt for classic, accent-free boots that hit about mid-calf or higher.

Here are a few good choices: 

Wearing Pumps With Leggings

Pointy-toed pumps with red suede uppers, and mid-height, covered wedge heels.
Belle by Sigerson Morrison 'Whitney 2' Image:

A lot of women pair leggings with high-heeled pumps. This combination is fine if you're channeling 1950s pinup girls or, if the leggings are shiny, 1970s disco divas. If that's the glam, retro look you're after, then by all means, have at the stiletto pumps and leggings. Remember, though, to wear a long shirt, tunic, skirt, or dress over the leggings. Otherwise, you'll wind up looking too stuffed into your outfit.

For a look that's easier to pull off, try wearing mid-height heels, pumps with wedge heels, or chunky-heeled pumps with your leggings. Ideally, the leggings should hit right at, or just below, the tops of the pumps.

Here are a few pumps to check out: 

Ankle Boots and Booties

Black western ankle boots with chunky low heels, unembellished suede uppers, and loose shafts.
Steven 'Welded' Image:

Wearing ankle boots with leggings can be somewhat tricky, but that doesn't have anything to do with the leggings. Actually, ankle boots, in general, are problematic for a lot of women. This is because of where the boots hit on the legs, which, as the name implies, is usually right above the ankles. On some women, the boots make the thickest part of the calf (the part just above the top of the boot) look even thicker and shorter. For that reason, ankle boots worn with leggings (or tights) are actually more flattering than when they're worn with bare legs.

Unless you actually want your legs to look shorter and heavier, you'll need to choose your legging/ankle-boot combination carefully. Avoid mixing very light-colored or pastel leggings with dark ankle boots. For a thinner, more cohesive appearance, choose dressier ankle boots; for styles that are a bit loose around your legs, match the color of the leggings to the ankle boots, and opt for dark colors on both the leggings and the boots.

Short booties can work really well with long leggings. Just follow the same general rules that you would for pairing tights with booties: Make sure your leggings cover your entire leg and pair the combination with a top, skirt, or dress that hits mid-thigh or lower.

Check out a few great ankle boots here: