How to Wear Ankle Boots in 2020 (Including 2 Styles to Retire)

Our favorite way to rock combat boots? With an outfit that totally opposes their tough vibe. Silk slip skirts, cream-colored knit sweaters and ladylike handbags put a sophisticated and modern spin on your lace-up footwear. Just make sure your skirt hits at mid-calf or higher, so your legs aren’t overwhelmed by too much fabric.

Shop similar styles: AllSaints combat boots ($348); BlankNYC leather jacket ($98); Everlane sweater ($95); Vince skirt ($265); Saint Laurent bag ($2,290)

If a black combat boot feels too severe for your style, there are a plethora of light options—and we're all about this sand hue. Keep the rest of your outfit equally light and airy, like a tie-dye jacket and straight-leg denim in a light wash. This is an instance where we’d suggest skipping wide-leg or a boyfriend cut jeans, as the excess fabric will look sloppy alongside this sometimes clunky footwear.

Shop similar styles: Dolce Vita boots ($200); Mother shacket ($345); Acne Studios bag ($800; $400); Trave jeans ($278; $201)

2. Hiking Boots

Don't worry, you don't have to be "outdoorsy" to opt into this bootie trend. Elevated takes on the footwear preferred by hikers can be found from a handful of brands—ranging from Aldo to Christian Louboutin. So, whether you're looking for a leopard pair to wear to the grocery store or are more interested in an all-weather shoe that can withstand a snowstorm, you'll find some cute hiking boots in your budget.

Falling somewhere between a dress and trousers, a jumpsuit is just the piece you'll want to wear with this season's updated take on the hiking boot. Mostly because it's not too dressy, nor too casual. Your best bet is to opt for a one-piece that's cropped right at the ankle, so it shows off the top of your boot and creates a long, flattering line from the waist on. And keep the rest of your rugged accessories to an absolute minimum—a sleek hat or simple purse will temper any outdoorsy vibes your shoes give off.

Shop similar styles: Marc Fisher LTD boots ($239); Missguided boilersuit ($72); Madewell hat ($32); Tularosa jacket ($248)

We'd argue that Timberlands are among the easiest hiking boots to wear (at least sartorially speaking)—and once you get your hands on a pair you'll understand why. Especially in black, they'll become your skinny jean's BFF and they'll find a surprising comrade in any pair of tapered pants. BTW, you'll be hitting two trends at once if you wear these booties with cargo pants, so go ahead and embrace the pocket-heavy life.

Shop similar styles: Timberland boots ($150; $120); Anine Bing pants ($200); LA Relaxed T-shirt ($30); J.W. Pei bag ($99; $59)

3. Snakeskin

Yes, the exotic animal print is still going strong into 2020. It doesn’t matter whether you prefer a more realistic gray or brown coloration, or if you go totally faux with red, purple or rainbow, so long as you wear ’em proud.

You know the saying "leopard is a neutral?" Well, the same could be argued for snakeskin, especially in shades of tan. As such, you shouldn't shy away from pairing these fierce booties with loud pops of color or statement-making outfits. Take, for example, this bold, ruched dress and teal handbag combo, which feels crisp, clean and so of-the-moment.

Shop similar styles: Aera boots ($525); Babaton dress ($178); Mansur Gavriel bag ($595)

Wondering how to wear snakeskin with another pattern? Almost anything goes, so you could rock yours with a striped turtleneck or a floral cardigan. Just one thing: try to avoid wearing this animalistic pattern with zebra or leopard print. This isn’t the zoo!

Shop similar styles: Sam Edelman booties ($150); Bernardo coat ($150); Madewell sweater ($90); Ann Taylor jeans ($89)

4. Rugged Chelsea Boots

They've got the reliably non-slip sole of the combat boots you know and love, but the pull-on-and-go ease of sleek Chelsea boots. If you're looking for an ankle-height kick that's equally stylish and ready to tackle inclement weather, you've stumbled upon a gold mine—and it looks so polished in brown or white leather.

Don't let the exaggerated silhouette of that sole psych you out; these kicks play well with patterns that skew on the more whimsical side. That includes both the quilted coat and the studded bag. Just don't discount how the addition of that chunky gold bracelet adds a super luxe feel to this entire look. See, sometimes the smallest details really do make the outfit.

Shop similar styles: Circus by Sam Edelman booties ($99); ASOS dress ($35); Ulla Johnson coat ($795); Baublebar bracelet ($38); Construct face mask ($25)

Hello, work-friendly uniform. While the black jacket, sweater and chino combo might feel ho-hum, the bold punch of these white booties definitely adds a welcome contrast. And don't forget to have fun with proportions here—you'll find it particularly useful for balancing out the width of your pants with the heft of your Chelsea boots.

Shop similar styles: Villa Rouge booties ($195); Mango trousers ($60); Everlane turtleneck ($120); Uniqlo coat ($150); Missoma necklace ($180); Danse Lente bag ($375; $150)

We weren't kidding when we said these sharp-toed beauties will be your daily footwear choice. See how they make a simple turtleneck look dressed up? Okay, so the blazer might have a little bit to do with that, but we think the cropped flare of these classic blues show off that unique boot shape. That's all you need to take a basic outfit and elevate it one notch.

Get the look: Franco Sarto booties ($180); Slvrlake jeans ($279; $109); H&M blazer ($50); Gap turtleneck ($70; $56); Les Specs sunglasses ($79)

This look feels polished enough for workdays and Sunday brunch with the crew. Not to mention, it's a simple combo that clearly isn't overwhelmed by the addition of an extra-large tote bag.

Get the look: Staud booties ($425); Alice McCall dress ($395); Feisedy sunglasses ($10); Isabel Marant tote ($145)

1. Retire: Disco Platforms

Sometimes referred to as "ankle breakers," we can all collectively enjoy a sigh of relief that these towering shoes are on their way out. While they did have their moment in the spotlight in 2019, these throwbacks to the Studio 54 dance floor should now be relegated back to the storage units they came from. And while it was nice to gain five extra inches of height, not being able to walk more than a block might have contributed to this short-lived bootie trend.

2. Retire: Cut-out Booties

Reassure your socks that their job is safe because cut-out booties are officially out. No longer do you have to suffer through chilly feet in February because your hoofs are out in the open. That said, the actual shape of the above booties—a winning combo of pointy-toe and kitten heel—is very much still en vogue. So go ahead and wear them...as long as they don't look like a cut-up paper snowflake.