How to Wear Ankle Boots With Dress (Pictures)

Ankle boots, also known as booties, are a wardrobe staple because they’re timeless, versatile, and (mostly) designed to be walkable. But do ankle boots go with dresses?

In this article, you will learn how to pair ankle boots with dresses, including the 3 rules to follow when pairing ankle boots with a dress. There are also many pictures for inspiration.

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Do ankle boots go with dresses?

Ankle boots go with dresses, as long as you show plenty of your legs (to make them appear longer). Mind the spacing between the bottom of your dress and the top of your ankle boots.

Rules to follow when pairing ankle boots with a dress

When it comes to pairing ankle boots with dresses, there are three rules to follow. No matter the ankle boots, these rules will make your outfit look universally flattering:

1. The shorter the ankle boots, the longer you can wear your dress

Remember this fashion rule: the shorter the ankle boots, the longer you can wear your dress. The opposite is true, too. The higher your boots, the shorter you can wear your hemline.

Shorter dresses work with ankle boots. Knee-length dresses, for example, work amazingly well with ankle boots because you are showing much of your legs, making them appear longer.

The goal is to make your legs appear as long and elongated as they can. You want to avoid wearing high-ankle boots with dresses that fall somewhere near the ankles.

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Where it gets tricky is when you are wearing dresses with longer hems. You can wear dresses that fall below the knees, just be conscious of the space between the dress and the boot.

2. Ankle boots with similar colors to your skin elongate your legs

While you want to choose neutral-colored ankle boots (so you can wear them with many outfits), it’s wise to pair ankle boots that come in similar colors to your skin tone to elongate your legs.

Some universally flattering ankle boot colors include nude/tan, white, and gray. A pair of skin-colored ankle boots will help create a nice, long leg line (almost as if you are barefoot).

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Black and brown ankle boots are popular neutral colors, but they tend to appear heavier and chunkier. They also “cut” your legs in half, making your legs appear shorter than they are.

Ankle boots that come in dark, contrasting colors work, however, if the shaft on each pair is slim around the ankles. They lend the appearance of a long and thin line running through your legs.

3. Choose ankle boots that make your legs appear longer

Last but not least, you should choose ankle boots that make your legs appear longer. For example, go for ankle boots with heels if you want a more slender look.

Ankle boots with heels are often preferred over flat ankle boots because they add length to the legs. They are often paired with shorter dresses to create the illusion of long, slender legs.

When wearing taller ankle boots, however, make sure the shafts hug your ankles. This lends the appearance of a nice, thin line running through your legs, as opposed to chunky feet.

A scoop front on an ankle boot is always a good option because it elongates your legs.

Sock booties can be tricky. Try to show as many legs as you can. I would recommend pairing a pair of sock booties with a shorter dress to avoid covering too much of your legs.

How do you wear ankle boots with a dress?

Shorter dresses work with ankle boots. Knee-length dresses, for example, work amazingly well with ankle boots because you are showing much of your legs, making them appear longer.

While it’s a matter of taste, sleek ankle boots generally pair well with elegant gowns, while chunkier, heavier booties look best with more casual dresses. Here are some guidelines:

1. Black ankle boots with a dark tight dress

Black ankle boots look best with dark dresses that end above the knee. The shorter your dress is, the longer your legs will appear. Anything that ends about mid-thigh would look fabulous.

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If the occasion calls for a longer dress, consider wearing some opaque tights that match the color of your boots. The ideal combination is black boots and black tights.

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Alternatively, you can also pair black ankle boots with light-colored dresses, so long as the dress falls above the knees. Anything below the knees would make your legs appear shorter.

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2. Brown ankle boots with colorful dresses

Brown ankle boots offer so much more versatility than black ankle boots in my opinion. You can easily pair brown ankle boots with colorful dresses, whether they are floral patterns or stripes.

This is why many women consider brown ankle boots as the ultimate summer footwear.

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When thinking about dresses and brown ankle boots remember they’re just like any other shoe, you just have to consider heel height and where the boot hits your ankle and calf.

If you want to look bright, try pairing a pair of brown ankle boots with a floral mini dress, a Midi linen dress, or a knee-length tailored cotton dress. Just make sure your legs are visible.

3. Nude/tan ankle boots with any type of dress

When it comes to ankle boot colors that are similar to the skin, line nude and tan, there are so many dresses you can pair them with. You can literally pair them with any type of dress.

Whether you pair nude/tan ankle boots with a bodycon dress, a Midi dress, or a Maxi dress, the natural skin color of the boots offers a long and streamlined appearance to your legs.

You can mix and match nude or tan ankle boots with dresses of different colors, as long as you follow the first rule which is: the shorter the ankle boots, the longer you can wear your dress. 

4. All ankle boots pair well with a Midi dress

A Midi dress, where the hem ends halfway between the knees and ankles, pairs surprisingly well with ankle boots. Unlike other dresses, longer Midi dresses are better with ankle boots.

Shorter Midi dresses that fall above the swell of the calves tend to be less flattering with ankle boots. Longer Midi dresses that hit above the ankles, on the other hand, are more flattering.

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You can literally pair any-colored ankle boots with any-colored Midi dress. As you can see in the Pinterest posts above, you can pair ankle boots with black, floral, tan, and purple dresses. 

Can you wear flat ankle boots with a dress?

You can pair flat ankle boots with many types of dresses, including Midi and Maxi dresses. Just be sure to follow this rule: the shorter the ankle boots, the longer you can wear your dress.

Key takeaways

Now you know how to wear ankle boots with dresses. The shape of your legs, the length of the dress, and the height of your boots are different factors you should always consider.

It all comes down to what works for your specific body type. The key is to be aware of the spacing between the bottom of your dress and the top of your ankle boots.

Related articles:

  • How to wear ankle boots with skirts
  • How to wear ankle boots with jeans