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What to Wear with Leggings

The Best Shoes and Boots

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Leggings are super-comfortable, and they can be worn with a variety of things, like long sweaters in the fall and winter, or thin tunics in the spring and summer. They also work well when worn like tights with shorter skirts and dresses.

But, one of the areas people seem to have trouble with is picking the right shoes and boots to wear with their leggings.

It's not difficult and, fortunately, there are a lot of choices. Below, I cover a few of your best footwear options for long leggings.

If you're wondering what to wear with shorter leggings, check out my article on the best shoes for capri pants.

Ballerina Flats and Other Flat Shoes

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

Ballerina flats are one of my favorite shoe styles to pair with leggings.

Both ballet flats and leggings are slim and streamlined, and the low cut of ballerina flats means that the top 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.

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 will rock with those. 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 flats, slingback flats, open-toed, and smoking flats, like the ones pictured here, also generally work well with leggings. But, remember to choose low-cut styles that leave some foot skin showing.

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

Perfect Combo: Leggings with Boots

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

Even though leggings will 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 because, when paired with mid-calf or knee-high boots, leggings nearly begin to look like tights, only they're much more substantial and opaque. Another reason it works is because tall boots will cover your calves, and help combat the leg-thickening effect that leggings often have.

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

Wearing Pumps with Leggings

Pointy-toed pumps with red suede uppers, and mid-height, covered wedge heels.
Belle by Sigerson Morrison 'Whitney 2' Image: Piperlime.com
A lot of women pair leggings with pumps. This isn't a combination I wear very often, but not because there's technically anything wrong with it -- it's just that the combination of leggings and high heeled pumps often conjures images of 1950s pin-up girls, or, if the leggings are shiny, 1970s disco divas.

As fun as those looks can be, neither of them really meshes with my own personal style. I'm much more of a 60s mod type.

But, if it's a glamorous, retro look you're after, then by all means, have at the stiletto pumps and leggings, but remember to wear a long shirt, tunic, skirt or dress over the leggings, less you wind up looking too... "stuffed" into your outfit.

If you want a look that's easier to pull off, try wearing mid-height heels, pumps with wedge heels, or chunky-heeled pumps with your leggings. It's also helpful if the leggings hit right at, or just below, the tops of the pumps.

Ankle Boots and Booties

Black western ankle boots with chunky low heels, unembellished suede uppers, and loose shafts.
Steven 'Welded' Image: Heels.com
Wearing ankle boots with leggings can be somewhat tricky, but that doesn't have anything to do with the leggings. It's 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 -- i.e., one of the thinner part of a woman's legs. So, what happens is the boots make the thicker part of the calves (the part just above the top of the boots) look even thicker -- and shorter.

For that reason, most women will find that wearing ankle boots with leggings (or tights) is actually more flattering than wearing them with bare legs.

But, unless you actually want your legs to look shorter and heavier, you'll still need to choose the combination carefully. Avoid mixing really lightly-colored, or pastel leggings with darker ankle boots. For a thinner, more cohesive appearance, choose dressier ankle boots, or styles that are a bit loose around your legs; match the leggings to the ankle boots; and opt for dark colors on both the leggings and the boots.

Shorter booties can also work really well with long leggings. To make it easy to choose the right style, just follow the same general rules that you would for pairing tights with booties: make sure the entire leg is covered by your leggings, and pair the combination with a top, skirt or dress that hits mid-thigh or lower on the legs.

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