How to Wear Dresses with Boots

Co-authored by Ashley Kahn

Last Updated: March 1, 2023 References

There are a variety of stylish combinations when it comes to pairing boots with dresses. With so many options, it can sometimes be difficult to find the right boot and dress combination. The choice doesn’t have to be difficult, however, if you follow a few simple guidelines. Whether you are wearing short or long boots, the variety of combinations to choose can be plentiful, even when keeping the guidelines in mind.

Method 1

Method 1 of 3:

Styling for the Occasion

1
Match the boots with the style of the dress. Try to pair the style of boots with the style of dress you’re wearing. For example, a pair of chunky, motorcycle boots wouldn’t work well with a light, flowing dress, but they would work well with a faux leather dress. Also, a pair of brown ankle boots wouldn’t look good with a leather dress, but they would work well with a light, flowing dress.^{[1]
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2
Wear boots that are formal or casual enough for the occasion. Along with matching the style of the boots with the dress, choose the right boots for the occasion. A pair of sleek, thigh-high boots might look good with a black dress, but it wouldn’t be appropriate for a fairly casual occasion. Instead, opt for a pair of chunky, ankle boots for a casual occasion.^{[2]
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- Make a black dress appear more casual and edgy by wearing a pair of chunky, leather boots with it.
- Wear high-heeled boots with the same black dress to dress the outfit up.
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3
Decide on tights or bare legs. Whether you wear tights or not largely depends on the weather. It is better to wear tights or leggings with your boots if the weather is cold, especially if the dress or short. However, if the weather is warm, it's perfectly fine to opt for bare legs.^{[3]
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Expert Source

Ashley Kahn
Wardrobe Stylist
Expert Interview. 30 September 2020.}
- For cold weather, wear a pair of thermal tights with long, faux leather riding boots.
- Wear a pair of flat ankle boots with denim shorts for warm weather.
4
Allow a few inches between the boot and dress. There are exceptions, but typically, you should leave at least a few inches of skin exposed between the boots and the hemline of the dress. Leaving at least a few inches exposed is usually more flattering. Even if you are wearing a long dress, try to wear boots that leave a “peek” of your legs.^{[4]
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- Shorter dresses are versatile—you can wear tall boots with them, if you'd like, or you can opt for short booties.^{[5]
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  Expert Source
  
  Ashley Kahn
  Wardrobe Stylist
  Expert Interview. 30 September 2020.}

Method 2

Method 2 of 3:

Wearing Short Boots with Dresses

1
Pair slouch boots with a fitted dress. Slouch boots are ankle boots that don’t fit tightly around the ankle. Pairing slouch boots with a short, fitted dress is a good way to keep the look laid-back. It is also a good way to make your legs appear slimmer.^{[6]
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- Wear black tights for an extra slimming look.
2
Make the look edgier with a flowing dress. This look is one exception to the guideline of pairing the boots with the style of dress. Wearing ankle boots with a flowing dress is a good way to add juxtaposition and a bit of edge to the style. Choosing motorcycle boots, however, may be too much of a juxtaposition.^{[7]
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3
Wear open-toe boots with a frock dress. A frock dress is a dress that was popular in the 1950s and is typically looser fitting except around the waist. Pair a mid-length frock with a pair of open-toe boots. The open-toe boots should be ankle length. The open-toe boots are a great way to add a touch of modern style to a retro look.
- Wear a floral frock dress with open-toe boots that match one of the colors in the dress.

Method 3

Method 3 of 3:

Choosing Long Boots with Dresses

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Choose a short dress with over-the-knee boots. A short dress with over-the-knee boots is a very cute and common choice. You can wear a tight, fitted dress, or a loose, short dress. Suede boots look good with a casual dress. Leather or pleather boots look better for a dress that is meant to be worn on a night out.^{[8]
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- Wear a short, flowing lace dress with a pair of brown over-the-knee boots.
2
Pair a knee-length dress with riding boots. Choose a loose, knee-length dress with a pair of tall riding boots. A cream-colored dress with a pair of light brown riding boots would be a good option for this look. This combination is casual, but elegant and can be worn at almost any time of the year.
3
Don’t show any skin between the dress and boots. This is the exception to showing skin between the dress and boots. Choose a pair of thigh-length boots of any type. Suede, velvet, and leather boots are a few options. Make sure the boots fit tightly around your legs. For more casual boots, wear a loose, floral dress. Wear a tight dress with high-heeled boots for a nighttime look.

Expert Q&A
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Question

Do I have to wear tights if I'm wearing a dress and boots?

Ashley Kahn
Wardrobe Stylist
Ashley Kahn is a Wardrobe Stylist based in Houston, Texas. With over 10 years of experience, Ashley styles women both in-person and virtually and is passionate about empowering women through the art of personal style. She believes every woman deserves to feel comfortable, classy, and confident every single day. Ashley holds a business degree from Sam Houston State University. She has been featured on KPRC's Channel 2 Houston Life and ABC 13's Check This Out Houston and in the Houstonia magazine. Ashley has also hosted Macy’s “The Wardrobe Edit” and the “It List” fashion shows.

Ashley Kahn

Wardrobe Stylist

Expert Answer

Support wikiHow by unlocking this expert answer.

No, it's completely acceptable to wear booties or taller boots and leave some skin showing. However, if it's cold, it's still fine to wear tights if you'd like.
Question

Do black motorcycle boots look good with black leggings, along with a black a-line skirt?

Boot Lover

Community Answer

All-black attire sounds good. They don't even have to be the same shade, as long as you think they suit you.
Question

I am wearing a to the knee dress to a wedding. Are boots appropriate and what kind?

F&j&c123

Community Answer

Beige boots are a good idea when you want to draw attention to the dress. A short heel and ankle high boot is cute.