How to Style Ankle Boots With Almost Every Look You Own

Ankle boots — or booties — are arguably the ultimate chilly climate shoe. With so many different options (heeled ankle boots and white ankle boots included), it’s often hard to get out of the trench of wearing the same reliable pair of shoes with the same tired outfits for a large number of weeks. Yet, simply sit back and relax — we’ve discovered some fresh groundbreaking ideas on how to wear booties with jeans, pants, dresses, skirts, and every wardrobe in the middle between. Searching for winter outfit inspiration? Look no further than these style combinations that make women’s ankle boots look quite stylish.

How to Wear Ankle Boots With Jeans

Wearing ankle boots with jeans is a great way to ease into the bootie pattern 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. Sleeve the hems — instead of getting 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 casual look, wear brown ankle boots with handcuffed jeans for relaxed energy. If you want to add an extra component 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

Dr. Scholl’s Women’s Rate Ankle Boot

Assuming you want flat ankle boots that you can wear with casual outfits, look at 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 getting things done. Pair these ankle boots with jeans for a comfortable yet stylish outfit.

Steve Madden Lynden Block Heel Bootie

For a tomfoolery pop of color, these patent-heeled booties will not 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 current pieces like jeans. That way, it will not seem like you are wearing a costume, and they will add crazy retro energy to your outfit. Best of all, the patent material is easy to clean — just wipe it with a damp fabric, and you should be all set.

ASOS Design Remmy Set Back Heeled Boots

Have you at any point considered how to wear ankle boots with straight-leg jeans? The key is to contrast the looser attack of denim with heeled ankle boots. That’s the reason we like this design from ASOS. The pointed toe and set-back heel give jeans a sharp, sophisticated look when worn together. The design and authentic-looking faux leather will trick even the most stylish spectator that these are designer pairs.

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 try the style out. Patterned boots and stout gems add a touch of edge to paper bag-waist pants and a slouchy, off-the-shoulder sweatshirt. Cropped flares ensure that your ankle boots stand out, while a slight heel gives you a little boost (so regardless of whether your legs are on the shorter side, the cropped pants will still be flattering).

The color palette in this outfit feels appropriate to fall; cranky hues like beige and black are a great neutral combination for the season. Take a stab at getting 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

House of Harlow X REVOLVE Nick Bo

The beauty of snakeskin booties? They practically are neutral thanks to the mix 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. Go ahead and coordinate your top with the neutral shades or simply pair them with brilliant colors for a crazy look.

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 stunt! A pointed toe and stacked heel play to the western pattern, yet the simple design keeps the booties current. To make your dress pants or trousers somewhat sassier and in vogue, these booties will add just sufficient attitude.

Vince Camuto Ellen 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 narrow toe and 3.75-inch heel for a savage look. Coming in snakeskin and rich suede shades, you should stock up on a couple of pairs.

How to Wear Ankle Boots With a Dress or Skirt

Ankle boots can also look unimaginably stylish when worn with a dress or a skirt, regardless of the length. Whether you’re shaking 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 gem-tone velvet skirt with studded booties and a bucket bag. A stylish 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 zoom-up bootie, similar to the one presented above, for a sleek, cool-young lady vibe.

Best Ankle Boots for Dresses

Steve Madden Hutch Black Bootie

We love haul-soled boots not just because they are the “it” boot of the season, yet in addition, because they are surprisingly practical. The thick treads make walking in the snow somewhat easier and the stout sole gives you level without pain. With its tomboy toughness, a carry-soled ankle boot like this one from Steve Madden looks amazing when contrasted with a more female dress or skirt. Choose between black and beige.

Louise Et Cie Jadran Pointed Toe Bootie

Attempting to match ankle boots with a dress that leans more toward the formal side? These elegant booties from Louise Et Cie are great. The special 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 supper or an important presentation at work, these boots will have you striding with certainty.