How to Wear Ankle Boots With Practically Every Outfit You Own

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

Jeans pair well with low-heeled and more casual ankle boots—but bold heels that can work with dressier clothes can also work beautifully here.

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.

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.

ASOS Design Envy 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 set back heel gives jeans a sharp, sophisticated look. The design will fool even the most stylish onlooker that these are a designer pair.

Vince Camuto Gigietta Suede Bootie

For a fun pop of color, these pretty suede booties won't disappoint—whether you opt for pink or a neutral brown or tan. The block heel will also look lovely with a skirt or tailored pants.

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

Consider heeled boots, with kitten heels or block heels, to add a more formal look that matches your dress pants.

Toms Kelsey Pull-On Wedge Bootie

Wedge booties work beautifully with wide-legged pants—whether you're sporting dressy trousers or casual baggy jeans.

Marc Fisher Gadri 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.

Lucky Borida Ankle Boots

A block heel ankle boot will give your favorite dress pants a sophisticated vibe.

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

Dresses can go with a range of ankle boot styles, from sophisticated peep-toe styles to rugged boots as a counterpoint to a more feminine dress.

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.

Michael Kors Lawson Open Toe Leather Bootie

Peeptoe ankle boots are perfect for wearing with dresses and skirts that usually get worn with sandals. This sleek pair is perfect with a little black dress.

Vince Camuto Kresinta Bootie

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.

Types of Ankle Boots—and How to Wear Them

There's plenty of variety when it comes to ankle boots—so how do you choose ankle boots that'll give you the biggest bang for your buck? Consider comfort, first and foremost. "Slight changes in styles, like heel height and width, can impact how much you’re able to wear them," says Courtney Busch, stylist at Stitch Fix.

Chelsea Boots

Busch recommends Chelsea boots—which are an easy, pull-on style with bands of elastic in the boot to help it slip over the foot—as as a great all-purpose pair of ankle boots. "Chelsea boots are a timeless choice that can elevate various looks," Busch says. "The sleek silhouette and ease to slip them on make them a closet staple for many—they're a versatile, trend-proof investment piece." They'll work with many different styles of outfits, but Busch likes them best with a matching pant and blazer set or jeans and a statement jacket.

Flat and Low-Cut Ankle Boots

Flat-heeled and low-cut ankle boots are the most casual ankle boot style (and probably the most comfy, with the lack of heel) so they're perfect for wearing with that classic fall combo of jeans and a loose, oversized sweater, Busch says.

Block or Chunky Heel Boots

Block heels tend to be thicker, sturdier heeled ankle boots, where the heel is made of stacked pieces of material. Busch recommends them as another great all-around boot, which can go with casual clothing or more formal looks.

Peep Toe Ankle Boots

Peep toes—as the name suggests—have openings in the toe of the boot to show off your pedicure. They're perfect for transitional seasons between summer and fall, or winter and spring. Busch likes them with skirts or dresses that you'd wear sandals with in warmer weather.  

Lace-Up Boots

Boots with shoe laces tend to be more casual in style, and work wonderfully with outfits that'd look great with sneakers, such as jeans with a sweater or a moto jacket.   

Kitten Heel Boots

Kitten heels are curvy sculpted heels, generally on the shorter side. And they're great for more dressy ensembles for work or evening. Busch recommends them with tailored trousers, a silk blouse, and a blazer—and they're great with dresses or skirts as well.

Wedge Heel Ankle Boots

Wedge heel ankle boots tend to be both sophisticated and comfortable, Busch says—and they're built with the heel and sole of the boot as a single piece in a wedge shape. They're great with flared jeans or wide-legged dress pants.