How to Pair Boots With Dresses

Tips and Suggestions for Looking Stylish

Not surprisingly, some women shy away from wearing boots with dresses. The perception of boots as informal and dresses as formal leads meany to think more in terms of jeans and casual pants when they're considering what to pair with boots. The reality, though, is that topping your favorite boots with dresses and skirts opens up a slew of new opportunities to use what's already in your wardrobe—and shopping your own closet as if it were a store is a great way to expand your fashion options.

Why the Look Works

The most important fashion rule, of course, is to wear what you like and makes you feel good—but there are a few reasons that make wearing boots with dresses a great idea:

  • It's flattering. Depending on the type of boots, this can be the most flattering combo you'll ever wear. This is especially true with tall boot styles, which help create a long lean, cohesive look. Additionally, women who are self-conscious about their legs find that mid-calf, knee-high, and over-the-knee boots allow them to wear skirts and dresses that they might not otherwise be comfortable in.
  • It's a great alternative to other boot-accented options. Let's face facts: Skinny jeans aren't very kind to a lot of us, and some occasions just aren't right for leggings. Dresses, however, come in so many styles that there are options for every figure type, and many work well with boots.
  • It's fun to wear. The right boot/dress combination—be it dressy or casual—creates a chic, polished, confident look that's quite addictive to wear. In fact, once you see how fashion-forward you look, you might wonder how you ever got along without pairing the two.

Getting the Dress-Boot Combo Right

Figuring out the pairing that looks and feels best on you is mostly a matter of experimentation, but here are a few ideas to get you started.

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Keep It Simple

For an easy look that works for just about everyone, pair a simple dress—like a sweater dress, a wrap dress, or even a long tunic—with a pair of sleek, tall, flat boots. If you like tights or fancy stockings, add them into the mix for a bit of pizazz, but skip really trendy boot styles and anything that's too defined. For example, a halter dress atop a pair of cowboy boots is too fussy for this look. Other than that, the simple approach is practically foolproof.

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Stay Balanced

Try a half-and-half approach: half of a dressy outfit, paired with something more casual; half-frilly with something more utilitarian; or half-glamorous with something really simple. Still, just say "no" to cowboy boots and ​sexy dresses, because both of those items fall under the "attention-getting" heading. A pretty cocktail dress with a pair of simple boots or a pair of Western boots with a plain but feminine dress can work, though.

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If You're Short...

Most boots look good on most body types, but ankle boots and booties are trickier to pair with dresses if you're not blessed with the height and legs of a supermodel. In general, if you have short-ish legs, you can lengthen your appearance by wearing a dress with tights in the same color as your boots. Another approach: Wear a high-waisted skirt or dress with ankle boots and no tights.

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Let Your Legs Show

A few inches of space between the tops of your boots and your dress helps you keep it casual and not too buttoned-down. For this look, combine a long dress or skirt with booties, a mini dress with over-the-knee boots, or a knee-length dress with mid-calf boots.

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Get Playful

Feeling a little spunky? Spice up a simple dress or skirt with a pair of patterned or printed tights and boots that are low enough to show them off.

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Mix It Up

Don't go with a single color from dress to boot; you'll look like you're wearing a uniform. Want to keep it elegant? Go for dresses, tights, and boots in the same color family—for example, layers of darks and lights in the same color family. 

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Pull It All Together

You can mix colors, patterns, and textures together effectively by tying them together with accessories that match in color or material. For example, a black leather boot paired with a black leather belt gives you a put-together vibe, no matter what else is going on with your dress.