The best shoes to wear with leggings in 2023 include chunky boots, running shoes, heels, sandals, DMs, slip-on sneakers, loafers, over-the-knee boots, ankle boots, flats, and sandals. Other options include suede ankle boots and leather or patent shoes.

Leggings are super comfortable and 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 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

Ballerina Flats and Other Flat Shoes
(Copyright © Pinterest).

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 flats, 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.

I recommend checking out this great pair of sandals by BC Footwear.

Perfect Combo: Leggings with Boots

Perfect Combo: Leggings with Boots
(Photograph: @timelesspetite/Instagram).

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

Wearing Pumps with Leggings
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A lot of women pair leggings with pumps. This isn’t a look I often go for, but it’s not because there’s anything technically wrong with it; it’s just that the combination of leggings and high-heeled pumps conjures up 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 meshes with my personal style. I’m 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

Wearing Ankle Boots and Booties With Leggings
(Copyright © Pinterest).

Wearing ankle boots with leggings can be somewhat tricky, but that has nothing to do with the leggings. Ankle boots are problematic for a lot of women.

This is because of where the boots hit on the legs, which, as the name implies, are usually right above the ankles, i.e., one of the thinner parts of a woman’s legs.

As a result, the boots make the thicker part of the calves (just above the top of the boots) appear 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 light-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, 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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