How to Wear Ankle Boots With Practically Every Outfit You Own

Plus the best ankle boots to shop.

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


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-Dr. Scholl's Women's Rate Ankle Boot

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.

how-to-wear-ankle-boots-Steve Madden Lynden Block Heel Bootie

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-ASOS Design Remmy Set Back Heeled Boots

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


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

how-to-wear-ankle-boots-House of Harlow X REVOLVE Nick Bootie

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-Marc Fisher Gardi Pointed Toe Bootie

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.

how-to-wear-ankle-boots-Vince Camuto Ellea Heeled Bootie

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


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-Steve Madden Hutch Black Bootie

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-Louise Et Cie Jadran Pointed Toe Bootie

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-Nine West Donda Heeled Booties

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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