From dresses to suits, here are a few fun ways to style this versatile shoe.

By Julia Marzovilla
Oct 01, 2020 @ 11:30 am
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If there is one type of shoe you can rely on from August to April, it’s a pair of ankle boots. Just like a white T-shirt, this footwear option is a seasonless essential, and there are so many ways to wear them throughout the year.

However, it might take some digging to discover the perfect pair to add to your closet. With so many options, from classic Chelsea boots to an evening-appropriate stiletto, the trick is finding one that will suit your personal aesthetic.

To help you out, we've narrowed down nine different, modern ideas for how to style ankle boots, along with key choices for recreating the look. Whether you’re stepping out in a mini dress or a brightly colored suit, you likely find all versions of the bootie are extremely versatile.

It's time to stow away your strappy sandals and lean into this perfect fall (winter, spring, and summer) piece.

Style Flatforms With a Mini Dress

If you’re unwilling to completely give up on summer staples, try swapping out your typical white sneakers for a pair of ankle boots. Combat boots are everywhere right now, and Doc Martens' Jadon Flatform Chunky Boots ($180; asos.com) are perhaps the most ubiquitous version of these. The dark color and bulkiness will create contrast against the light floral and neon dresses you’ve been living in, toning them down for the cooler months ahead.

Wear a Sleek Pair With Wide-Leg Jeans

The most basic yet classic way to wear ankle boots? Under slightly cropped, wide-leg jeans. To really nail the look, choose a black pair that is tighter and hits higher up on the ankle (Shop Similar: $795; brothervellies.com), which will work to create a seamless (uncut) line and elongate your legs. To create a French-girl aesthetic, wear other pared-down pieces with your jeans and boots, such as a sweater set.  

Try Bright Boots With an Otherwise Simple Look

Who said ankle boots have to be basic or even neutral? A fun — and easy! — way to brighten up your outfit is with a vibrant pair of booties. Try styling a classic floral or black dress with red ankle boots (Shop Similar: $140; nordstrom.com) give your look that extra pop.

Elevate Your Sportswear

Even the most casual of outfits get a high-fashion twist with ankle boots. Case in point: this booties-and-joggers ensemble. A typical track suit suddenly seems dressy with the help of a heel, and it's smart to go with booties that hit higher on your ankle (Shop Similar: $398; nordstrom.com), so that tucking in your pants is a breeze. 

Create an Easy Utilitarian Look

Not only is it perhaps the quickest outfit solution when you’re running late, but you'll also come across effortlessly cool and casual for whatever you have going on. For added style points, coordinate the colors of your shoes with your accessories, or try a nontraditional pair with embellishments (Shop Similar: $650; stuartweitzman.com).

Try Chunky Boots Over Sheer Socks or Tights

Autumn equals tights season, aka the ideal way to make mini skirts and dresses a teensy bit warmer. However, if wearing tights reminds you too much of your grade school uniform, opt for sheer socks instead. Adding chunkier boots (Shop Similar: $165; shopbop.com) will keep your outfit from looking to preppy.

Balance Out Oversized Sets With Slim Booties

While barely-there sandals were a summer suit essential, ankle boots are their much-needed replacement in the fall time. When wearing a plain shorts suit or loose-fitting set, go for ankle boots with an eye-catching detail such as a metallic heel (Shop Similar: $325; katmaconie.com) in order to add some sparkle. 

Couple Flat Boots With A Maxi Dress

You don’t need a pair of heels to give your maxi dress a boost. Instead, try a flat pair of boots that will keep you warm and prevent your feet from hurting throughout the day. Boots made from a reflective fabric or include tons of buckles or zippers (Shop Similar: $490; us.maje.com) will add some interest to your outfit. 

Keep Things Coordinated

When wearing a monochromatic or color-blocked look, don't stop at your shoes. Instead, dare yourself to work in a bright pair of ankle boots of a similar or contrasting color scheme (Shop Similar: $55; asos.com), ensuring your outfit really shines.

For more of the latest trends, tricks, and style news, head to Future of Fashion.