How to Wear Ankle Boots With Practically Every Outfit You Own (2023)

Ankle boots—or booties—are arguably the ultimate cold weather shoe. With so many different options (heeled ankle boots and white ankle boots included), it's often difficult to get out of the rut of wearing the same tried-and-true pair of shoes with the same tired outfits week after week. But don't worry—we've found some fresh new ideas on how to wear booties with jeans, pants, dresses, skirts, and every wardrobe essential in between. Looking for winter outfit inspiration? Look no further than these style combinations that make women's ankle boots look oh-so-chic.

How to Wear Ankle Boots With Jeans

How to Wear Ankle Boots With Practically Every Outfit You Own (1)

Wearing ankle boots with jeans is a great way to ease into the bootie trend if you're just not sure what to pair them with. Whether you are dressing your jeans up or down, there are different types of ankle boots you can wear to stylishly assist in the process.

Cropped jeans and ankle boots are a match made in heaven. Cuff the hems—instead of tucking them into the boots—for some major ankle action. The cropped hemline creates a frame for showing off your favorite booties. If you're going for a really casual look, wear brown ankle boots with cuffed jeans for a relaxed vibe. If you want to add an extra element of style to your denim outfit, make sure your booties have a pop of color. Finally, pair the look with an oversized sweater for a casual fall ensemble that still looks polished.

Best Ankle Boots for Jeans

How to Wear Ankle Boots With Practically Every Outfit You Own (2)

Dr. Scholl's Women's Rate Ankle Boot

If you want flat ankle boots that you can wear with casual outfits, check out this style from Dr. Scholl's. It has a flat heel and memory foam insoles to keep your feet comfortable, so you can wear these all day while running errands. Pair these ankle boots with jeans for a comfy yet chic outfit.

(Video) How To Wear Ankle Boots

How to Wear Ankle Boots With Practically Every Outfit You Own (3)

Steve Madden Lynden Block Heel Bootie

For a fun pop of color, these patent heeled booties won't disappoint. Choose from bold hues like pink, blue, and white or stick to the basics of black and brown. With a 4-inch heel, these '60s-inspired booties look best when paired with modern pieces like jeans. That way, it won't seem like you are wearing a costume, and they will add a funky retro vibe to your outfit. Best of all, the patent material is easy to clean—just wipe with a damp cloth, and you should be good to go.

How to Wear Ankle Boots With Practically Every Outfit You Own (4)

ASOS Design Remmy Set Back Heeled Boots

Have you ever wondered how to wear ankle boots with straight leg jeans? The key is to contrast the looser fit of the denim with heeled ankle boots. That's why we like this design from ASOS. The pointed toe and set back heel gives jeans a sharp, sophisticated look when worn together. The design and authentic-looking faux leather will fool even the most stylish onlooker that these are a designer pair.

How to Wear Ankle Boots With Dress Pants or Cropped Pants

How to Wear Ankle Boots With Practically Every Outfit You Own (5)

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Ankle boots look just as great with dress pants and cropped trousers as they do with denim, so step outside of your comfort zone and give the style a whirl. Patterned boots and chunky jewelry add a bit of edge to paper bag-waist pants and a slouchy, off-the-shoulder pullover. Cropped flares ensure that your ankle boots stand out, while a slight heel gives you a little boost (so even if your legs are on the shorter side, the cropped pants will still be flattering).

The color palette in this outfit feels appropriate to fall; moody hues like beige and black are a great neutral combination for the season. Try tucking your pants into ankle boots for an ultra-stylish look that works just as well at work as it does on the weekend.

Best Ankle Boots for Dress Pants

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House of Harlow X REVOLVE Nick Bo

The beauty of snakeskin booties? They practically are neutral thanks to the blend of black and brown shades and thus go with nearly every outfit. This style's cool pattern and pointed toe deserve to be shown off, so a cropped pair of pants will do them justice. Feel free to coordinate your top with the neutral shades or simply pair them with a bright color for a funky look.

How to Wear Ankle Boots With Practically Every Outfit You Own (7)

Marc Fisher Gardi Pointed Toe Bootie

Want to add some western flair to your outfit without investing in cowboy boots? This pair from Marc Fisher does the trick! A pointed toe and stacked heel play to the western trend, yet the simple design keeps the booties modern. If you want to make your dress pants or trousers a little more sassy and trendy, these booties will add just enough attitude.

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How to Wear Ankle Boots With Practically Every Outfit You Own (8)

Vince Camuto Ellea Heeled Bootie

Croc-embossed booties are another great way to spice up your shoe game while still keeping it office appropriate. This style from Vince Camuto has a pointy toe and 3.75-inch heel for a fierce look. Coming in snakeskin and rich suede shades, you might want to stock up on a few pairs.

How to Wear Ankle Boots With a Dress or Skirt

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Ankle boots can also look incredibly stylish when worn with a dress or a skirt, no matter the length. Whether you're rocking a maxi skirt on the weekend or sporting a midi dress to work, there is an ankle boot that will work with your outfit.

This neutral sweater dress and versatile black boots make for a great style combination. Play with texture by mixing a jewel-tone velvet skirt with studded booties and a bucket bag. A chic high-low turtleneck streamlines the look. A maxi dress can also have a major impact with the right bootie peeping out from beneath the fabric. Consider a black zip-up bootie, like the one pictured above, for a sleek, cool-girl vibe.

Best Ankle Boots for Dresses

How to Wear Ankle Boots With Practically Every Outfit You Own (10)


Steve Madden Hutch Black Bootie

We love lug-soled boots not only because they are the "it" boot of the season, but also because they are surprisingly practical. The thick treads make walking in the snow a little bit easier and the chunky sole gives you height without pain. With its tomboy toughness, a lug-soled ankle boot like this one from Steve Madden looks amazing when contrasted with a more feminine dress or skirt. Choose between black and beige.

How to Wear Ankle Boots With Practically Every Outfit You Own (11)

Louise Et Cie Jadran Pointed Toe Bootie

Trying to match ankle boots with a dress that leans more towards the formal side? These elegant booties from Louise Et Cie are perfect. The unique combination of suede and smooth leather makes these more than just another pair of black booties. A pointed toe and sculptural heel give the boots a sophistication that could easily go with a midi skirt or a dress that hits above the ankle. Whether you're dressing up for a fancy dinner or an important presentation at work, these boots will have you striding with confidence.

How to Wear Ankle Boots With Practically Every Outfit You Own (12)

Nine West Donda Heeled Booties

Add just the right amount of edge to your outfit by wearing these studded ankle boots with a dress. Made with real leather, these booties are designed to last. The flattering rounded toe, smooth leather, and rich shades ground the boot in elegance while the studs add some attitude, so they are easy to dress up or down.

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What outfit can I wear with ankle boots? ›

How to Wear Ankle Boots: 6 Styling Tips
  • Go for a casual look with jeans. ...
  • Make a fashion statement with a bold boot. ...
  • Pair with a biker jacket. ...
  • Style with a classic white T-shirt. ...
  • Try high-heeled ankle boots with a dress. ...
  • Wear closed-toe booties to the office.
Mar 2, 2022

Are ankle boots still in style 2022? ›

In 2022 it's back stronger than ever, already spotted as the star of many great street-style looks, both in its full-length version and the ankle boot one.

Can you wear boots with everything? ›

Hot take: There's no style of footwear more versatile than the leather boot. Sure, I'm a little biased, but in truth, boots go with everything. Need a classy date night outfit? Pair slick chinos and a button-down with your go-to Chelseas.

Can you wear ankle boots with any dress? ›

You can wear them in any color or dress, and they'll look great. Of course, the style of ankle boots can dictate the look. Wide ankle boots, such as slouchy or Western styles, will make your outfit more casual, especially in opaque black materials.

Should I cuff jeans with ankle boots? ›

Cuffing jeans works best with ankle boots, because the cuff will fall right at the top of your boots. You can cuff straight-leg jeans and boot-cut jeans. Alternatively, you can also wear ankle jeans or cropped jeans with ankle boots—the jeans will naturally fall at your ankles so you will not need to cuff them.

Is it OK to wear socks with ankle boots? ›

It's best to avoid wearing them sans socks, as to keep them smelling their very best, for as long as possible (and, of course, to prevent freezing your feet off when the temps drop). As it turns out, though, pairing ankle boots with socks can actually look very stylish, and fashion girls have nailed the combo to a T.

What season are ankle boots for? ›

Technically, you can wear them during any season, but the two seasons that warrant their use the most are spring and fall. The in-between, mild temperatures don't really require winter boots, but they're too cold for summer sandals and maybe even flats.

What color boots go with everything? ›

Black just goes with everything.

A quality pair of black boots can be worn with everything short of a tailored suit or a tuxedo...and truth be told, will actually work with a tux if you get the right shine on them. That's almost always been the refrain when it comes to black vs. brown boots.

Can you wear ankle boots with a dress and tights? ›

One look we've learned to fall back on is dresses with tights and boots. The simple combination makes for an easy way to take your warm-weather pieces into a new season altogether. With the addition of tights and ankle boots, even the floatiest slip can work under the right circumstances.

How to wear ankle boots over 50? ›

roll up and leave 1/2″ of ankle between the boot and your pant. You can fold over twice to have a narrow cuff or one large fold. Be aware, the wider the cuff, the shorter your legs will look. If you cuff your jeans, wear a shorter top to help elongate the look of your legs.

Is it OK to wear ankle boots with leggings? ›

embrace Colors And Textures

Making printed leggings work with ankle boots is tricky business, but it absolutely can be done. Try to stick to classic black or dark brown footwear, to give your funky leggings a solid base. Then, add a textured knit in a complementary color up top.

Do you tuck pants into ankle boots? ›

For a long, lean line, tuck the pants into the boots.

This works best with legging jeans where the leg opening at the ankle is small and they fit snug to the leg. You don't want them to look bunchy. If they're going to bunch, you're better off cuffing them.

Where should jeans sit with ankle boots? ›

The first is to look for a pair of jeans that are slightly cropped so that they hit just above the ankle boots. Another way to make jeans that aren't cropped work with ankle booties is to do a messy roll so the jeans sit on top of the ankle boots.

Are ankle boots out of style? ›

Ankle boots at all are outdated

Although the seemingly controversial sock boot is generally a higher boot, it seems that shorter boots are on their way out overall. Per Who What Wear, ankle boots (and not just those with rounded toes) aren't as fashionable as they once were.

When can you stop using ankle boots? ›

Your doctor may have you use a boot for 1 to 6 weeks. How long you wear it depends on how serious your injury is. Walking boots are removable, and most of them can be adjusted. Your doctor will show you how to remove and adjust your boot.

What socks to wear with ankle boots 2022? ›

As a general rule of thumb, taller boots work best with knee or over-the-knee socks, while shorter styles (think trouser or crew socks) pair well with ankle boots or booties.

Do you wear ankle boots with ankle pants? ›

Wearing booties with cropped or ankle-length pants can create an incredible style, too. This is a great pairing for transitional looks in the fall and spring. One way to pull off the look with shorter trousers is to wear booties that have some type of cut-out, such as those with an open-toe style.

Can I tuck my pants into my boots? ›

If you're wearing skinny jeans, tucking them into your boots are probably your only option. The good news is, you'll look great doing so! It's a fun and playful look. We don't suggest tucking in your jeans if wearing a bootcut.

How do you wear 2022 boots? ›

Here are the 5 rules for making winter boots look fashionable.
  1. stick with leggings or skinny jeans for easy tucking. ...
  3. make boots look chic by repeating colors. ...

What Colour ankle boots go with everything? ›

If you're completely stuck and you're not sure which to choose, go with a standard brown pair of boots. You can always get a second pair in any color you want. But brown leather is going to give you the most versatility.

Should ankle boots be tight or loose? ›

Different styles of ankle boot will have a slightly different fit, but generally, your boots should fit nice and snug around your ankles without feeling too tight or too loose. One way to tell if your boots fit properly is to pop a finger between the back of your ankle and your boot.

What is the purpose of ankle boots? ›

What are some reasons to wear a walking boot? The walking boot protects the foot and ankle from different kinds of injuries such as sprain, shin splint, heel spurs, plantar fasciitis, and broken foot too.

Which Colour shoes is best for all outfits? ›

Neutral-hued shoes are fantastic because they go with anything, including all colors, patterns, and prints. In this case, it's best to stick to basics like black, white, cream, beige, brown, and gray, or switch things up and choose navy, which, yes, is considered neutral, too.

What shoe color is most versatile? ›

Black, beige, and grey shoes go with anything. Since they are all neutrals, you can wear these colors to offset a more vibrant outfit. Of course, with these neutrals, you can either mix and match or keep them in a similar tonal family. For example, there can be warm beiges and cooler beiges.

What kind of jeans can I wear with ankle boots? ›

TLDR: You can wear ankle boots with skinny jeans that are cuffed, tucked in, rolled under or with a pair of jeans that hits at the ankle. If your booties are short, don't tuck them in. If your booties are tall, they'll look best with tucked-in skinny jeans.

What length pants to wear with ankle boots? ›

Your straight leg or skinny pants and jeans that end several centimetres above the top of your ankle boots are an ideal pairing. There's no need to make that space with a cuff or roll because it is already there.

Do I tuck skinny jeans into ankle boots? ›

Tuck Skinny Jeans Into Ankle Boots

Skinny jeans weren't meant to have anything layered under them. That's why tucking your skinnies into your ankle boots is a no-brainer. This combination looks great with your longer, snugger jeans that will reliably stay put when you wear them with a shorter boot.

Can you wear skinny jeans over ankle boots? ›

Ankle boots are the perfect pair of shoes for light downpours and paired with skinny jeans, they're a go-to outfit for most women.

Can I wear a short dress with ankle boots? ›

Ankle boots can also look incredibly stylish when worn with a dress or a skirt, no matter the length. Whether you're rocking a maxi skirt on the weekend or sporting a midi dress to work, there is an ankle boot that will work with your outfit.

Can you wear ankle boots if you are short? ›

You've heard this tip before, and it's especially true for shorties. If you're wearing your ankle boots with boyfriend jeans, please, whatever you do, roll up your hem. The sweet spot is about a half inch above the boot, so a little ankle shows and elongates your legs.

How do you wear ankle boots in your 50s? ›

roll up and leave 1/2″ of ankle between the boot and your pant. You can fold over twice to have a narrow cuff or one large fold. Be aware, the wider the cuff, the shorter your legs will look. If you cuff your jeans, wear a shorter top to help elongate the look of your legs.

Can I still wear skinny jeans with boots? ›

Tucked into a pair of knee-high boots

Pairing your skinny jeans with your knee-high lug sole boots is a prime example of combining old trends with new ones. How else are you going to show off your knee-high boots when it's too cold to wear shorts or a mini skirt? Skinny jeans to the rescue!

Can you wear ankle boots with bootcut jeans? ›

Leather ankle boots are a staple with all kinds of clothing, not just jeans. But ankle boots and bootcut jeans fit perfectly together. You just need to figure out what style you're going for in your look.

Do leggings and ankle boots go together? ›

Black leggings and minimalist black booties will always look cool together, especially when worn with an oversize button down or chunky knit…or both. Don't be afraid to resort to the tried-and true if you're strapped for more out-of-the-box ideas. There's a reason these looks are considered classics.

How do you wear flat ankle boots with a dress? ›

Flat ankle boots match nicely to more casual dresses, such as a skater dress, t-shirt dress or a comfy sweater dress. Flat ankle boots make for the most comfortable ankle boots, and are perfect for day-to-day wear. They suit everyone and can look really stylish.


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