How to Wear Ankle Boots With Dresses

Last Updated: January 31, 2023 References

Have you ever wondered how to wear those cute ankle boots in the back of your closet with your favorite dress? Now you can find out and explore a whole world of fashion behind dresses with ankle boots.

Part 1

Part 1 of 3:

Choosing the Perfect Boot

1
Pick boots in neutral colors so that you can wear them with more outfits. Black and brown are the most popular neutral colors. You can also try nude/tan, white, and gray as well. Silver and gold are also both considered to be neutral and are ideal for evening looks.
- Plan ahead. Avoid mixing contrasting colors, such as white booties and a black dress. This will "cut" your legs in half, and make them appear too short.
2
Go for boots with a heel if you'd like to make your legs appear longer. The more slender your heel is, the more chic and sophisticated your outfit will look. A sleek, slender heel is also ideal if you want a more dressy look.

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3
Wear boots made from a matte material if you have large feet. Shiny materials make things look bigger. Matte materials, such as leather, suede, or canvas, make things appear smaller.^{[1]
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Go for boots with a wider cuff if you want your legs to appear slimmer. Ideally, the cuff of the boot should extend just past the ankle as well.^{[2]
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Research source} You might also want to skip excessive details, such as heavy embellishment or lots of straps. These will only add bulk to your boots, and thus to the ankle area.^{[3]
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5
Consider boots with rounded toes and a shorter heel if you will be on your feet a lot. These styles tend to be more comfortable than ones with high heels and pointed toes, especially after hours of walking. They are ideal for casual, day-time looks.^{[4]
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Consider boots with pointed toes and a higher heel for special occasions. The pointed toes and higher heels automatically make these styles look fancier than their casual counterparts. They are feminine and great for elongating the leg. They are ideal for date nights where you won't be doing a lot of walking.^{[5]
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Choose boots that flatter your body shape. Depending on what body shape you have, different boot styles will help balance your body out. Listed below are some ideas based on the four main body types:^{[6]
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- If you have a pear-shaped body, your hips are wider than your shoulders. Opt for a simple pair of ankle boots with a heel.
- If you have an inverted triangle shape, your shoulders are wider than your hips. Try a pair of brightly colored boots. Heavily-embellished styles will also work. This will give the illusion of curvier legs.
- If you have a rectangle body shape, your hips, waist, and shoulders are the same size. Try a pair of detailed boots, as this will give the illusion of curves.
- If you have an apple body shape, your widest point will be your waist or torso. Opt for a pair of brightly colored or heavily-embellished boots. This will draw the attention away from your waist, and give the illusion of curves.
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Choose boots that flatter your body type and make your legs appear longer. Much like body type, different boot styles will help balance things out like height, curves, or lack of curves. Listed below are some ideas based on different height and size combinations:^{[7]
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- If you are short and slim, go for heeled boots that cover the ankle. This will make your legs appear longer. Avoid boots that end at or below the ankle.
EXPERT TIP

Kathi Burns, CPO®
Image Consultant
Kathi Burns is a board certified Professional Organizer (CPO) and Founder of Organized and Energized!, her consulting business with a mission to empower people to master their environment and personal image by assisting them in taking control, making change and organizing their lives. Kathi has over 17 years of organizing experience and her work has been featured on Better Homes and Gardens, NBC News, Good Morning America, and Entrepreneur. She has a BS in Communication from Ohio University.

Kathi Burns, CPO®
Image Consultant

Our Expert Agrees: If you're comfortable with showing more leg, go with a boot that doesn't go past your ankle. If you like more coverage, however, choose a taller boot. Both styles look great and can be stylish parts of a wardrobe!
9
If you are petite and curvy, choose boots with a pointed toe. This will extend your legs, and give you a longer, sleeker look.
- If you are tall and curve, skip the cuff details. Too much detailing along the cuff will draw too much attention to your calves, and make them appear thicker than they actually are. Instead, opt for plain cuffs.
- If you are tall and slender, you can go with any style of boot.

Part 2

Part 2 of 3:

Choosing the Right Dress

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Consider dresses that end above the knee for the most flattering look. Anything that ends about mid-thigh would be ideal. The shorter your dress is, the longer your legs will appear. Long dresses (knee-length and loner) are generally not recommended for ankle boots, as they tend to shorten the leg.
- If you must wear a longer dress, consider wearing some opaque tights that match the color of your boot. The ideal combination is black boots and black tights. This will make your legs appear longer.
2
Wear longer and maxi-length dresses with care. Long dresses are generally not recommended for booties, because they tend to make the legs appear too short. You can resolve this by getting a dress whose hem ends just above the boot. If you want to wear a maxi-length dress, try one with a slit up the side.^{[8]
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Research source} Both of these tricks will help keep your legs from looking too short or stumpy.
- Try pairing longer dresses with fancier boots that have slimmer heels and toes. Casual boots, with wide cuffs and chunky heels will look better with shorter dresses.
3
Consider a simple dress if you plan on wearing lots of accessories. This will allow your accessories (such as wide belts and layered boho necklaces) really shine through without making your outfit appear too cramped. The dress can have a pattern on it, if you'd like, but tone down the embellishments, such as beading and embroidery.
4
Avoid wearing sleek, sheath dresses with boots that are too chunky. Bulky, heavy boots will "weigh" the dress down. Some embellishments, such as a simple strap, won't take away from the look, however.^{[9]
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Choose a dress based on your body type to make your legs appear longer. Depending on what sort of dress your wear with your booties, you can draw the focus away from certain areas, and direct it to others. Here are some tips based on different body types:^{[10]
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- If you are short and slim, try bubble skirts, rompers, and mini dresses. To make your legs appear longer, wear some opaque tights that match the color of your boot.
- If you are petite and curvy, try an A-line dress that ends just above the knee if you are petite and curve. Avoid wearing dresses that end below the knee, as this will make your legs appear shorter.
- If you are tall and curvy, try a long tunic-type dress or a semi-voluminous dress with dark tights. This will help make your legs appear more slender.
- If you are tall and slender, try a dress that ends just above the knee.
6
Mix and match boots and dresses with care. Not all boot styles go well with all dresses. Creating contrast between boot and dress styles can make a boring outfit look more interesting. The wrong type of contrast, however, can make your outfit look clashy, and not in a good way. For example, thick, chunky booties won't look good with a lacy evening dress.^{[11]
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Research source} Here are a few tips to keep in mind when putting your outfit together:^{[12]
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- Pair boots with pointed toes and slender heels with fancier dresses. Pair boots with rounded toes and flat or chunky heels with casual dresses.
- Try sleek dresses with boots that have sleek heels. If your dress is simple, then you can go wild with the accessories.
- Try cowboy styled boots with high-waisted dresses for that vintage feel.

Part 3

Part 3 of 3:

Creating Different Looks with Accessories

1
Incorporate your boots' style into your accessories, but be sure to match your dress. Note any details on your boots, such as studs or beaded trim. Choose accessories, such as belts or jewelry, that match these details. If your boots are plain, look at the style of your dress instead.
- If you are wearing simple, leather boots and a boho styled dress, try adding a wide, leather belt, some feather earrings, and a rustic necklace made from natural stones.
- If you are wearing a simple dress with leather, studded boots, try adding a matching, studded leather belt, and some silver jewelry.
- Leather ankle boots, a sleeveless tribal patterned midi, a long necklace, and a fedora all look fabulous for a boho look.
2
Play around with layering by adding a jacket. Something as simple as a matching jacket can make a flirty, girlish outfit look more formal and business-like. For example, a fit and flare dress with slender-heeled booties will give you a flirty and girlish look. Adding a jacket and/or belt over the dress will immediately give you a more businesslike look.^{[13]
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Tone down the accessories if your boots are heavily embellished. If your boots already have a lot of zippers, studs, or straps, you might want to keep the rest of your outfit looking simple. This also includes your dress. Instead, try a simple belt, scarf, or a pair of stud earrings.^{[14]
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Research source} If your accessories and dress are too detailed as well, your entire outfit will look too busy.
4
Spice up the accessories if your boots and dress are simple. A simple dress and boots are like a blank canvas. Try adding some longer earrings and a statement necklace. You can also play around with other accessories, such as a belt, bag, and hat or scarf. Try not to go overboard with your accessories however; if you add too many, your outfit will appear too cluttered.
5
Try some patterned tights if your dress and boots are simple. Black tights and black booties are great for making your legs appear longer, but they won't make your outfit look very interesting. Patterned tights, however, will.^{[15]
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Research source} Make sure that your patterned tights match your outfit somehow. For example, if your dress has roses on it, try tights made from lace with a rose design. If your boots have a chevron print on the cuff, try tights with a chevron weave.
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Add a belt to make your waist look slimmer.^{[16]
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Research source} For a more boho look, try a wide, leather belt over a flowing dress made from cotton or linen. For a more chic look, try a slim belt over a plain sheath dress with slender-heeled boots.