The Top Boot Trends For Winter—And How To Rock Them

Boot season is officially upon us, and per usual, we’re pretty pumped about it. Few closet staples stand out more during the fall and winter seasons than boots. They go with everything, can be dressed up or dressed down, and keep your feet comfy and cozy during the colder months. “Boots are always a go-to when it comes to fashion, especially once we hit the fall,” says Ali Levine, celebrity stylist and founder of the podcast Striptd Down With Ali Levine.

The only drawback about boots is that styles come and go fast. “One year low boots with a square shape may be in and the next it could be over-the-knee boots with a pointed tip,” Levine says. “It really depends on the designers and what we are seeing on and off the runway.” The good news: This season's styles are all about practicality, and considering, well, all things 2020, we're pretty happy about that. From timeless ankle booties to edgy biker boots and lace-up styles, here are some of the top boot trends to wear this winter.

Knee-High Boots

If there is one style that stands the test of time, it's the knee-high boot—and it doesn’t seem to be going anywhere any time soon. “It’s a great boot for any wardrobe and can be worn from morning to night,” says Levine. Just opt for a comfortable block heel that you can wear all day. For a sophisticated workday look, pair them with a sleek midi-skirt and double-breasted overcoat; to elevate your weekend style, wear with jeans and a leather jacket or with a t-shirt dress for off-duty-model vibes.

Shop this style: 

Sam Edelman Davis Knee High Boot ($250;

Silent D Comess Knee-High Boots ($158; 

Kenneth Cole Levon Leather Knee-High Boot ($240;

Steven New York Limo Pointed Toe Boot ($150;

Free People Grayson Tall Boots ($298;

Lace-Up Boots

“Even the simplest detail can really romanticize a shoe,” says Levine, adding that laces can soften a harsher boot. “You can pair them with so many outfits, too, taking your look in any direction—from casual and relaxed to sophisticated.” She likes pairing them with faux leather leggings or the season’s feminine dresses.

Shop this style: 

Sorel Women's Cate Block Heel Booties ($190;

Naturalizer Callie Boot ($170;

Sam Edelman Lydell Boot ($150;

Tory Burch Miller Lug Sole Bootie ($498;

Aerosoles Elena Boot ($195;

Moto Boots

Levine believes that everyone could use an edgy boot in their closet. “Dress it up, dress it down—I love what the biker boot can do for pretty much anyone’s wardrobe,” she says. “The style adds a masculine touch to an otherwise feminine look.” On that note, the clunky shoe looks just as cool paired with tapered jeans as it does with a sweater dress, and like a good moto jacket, the more worn the boot, the better it looks. (That's why stylists suggest investing in a high-quality pair that will last years to come.)

Shop this style:

See by Chloe Janis Flat Boots ($495;

AllSaints Donita Boots ($348; 

Frye Veronica Bootie ($279;

Kendall + Kylie Rad Vegan Boot ($65;

Jimmy Choo Leather Moto Boots ($950;

Square Toe Boots

Square toe boots are shaking things up this season. “ Square toes make a subtle statement and can change up the entire look of what you’re wearing below the waist by adding an expensive edge or sharpness,” says Levine. Have fun with this style, she adds, choosing prints, colors (red alert!) or details you wouldn't normally be drawn to. And pair them with cropped jeans or a midi skirt, keeping the boot the statement.

Shop this style: 

Franco Sarto Harmond Mid Shaft Boots ($120;

Alohas West Black Vintage Leather Square Toe Ankle Booties ($184;

Sam Edelman Olina High Heel Booties ($180;

Reike Nen Cube Heel Basic Boots ($510;

Alexander Wang Lane Square Toe Bootie ($695;

Chelsea Boots

This list wouldn't be complete without the timeless Chelsea boot. Understated yet chic, these close-fitting, ankle-high boots are super versatile, and they anchor any outfit, says Levine. “They’re basically like the LBD version of a shoe.” Stick with neutral colors like black and camel, and look for a classic cap-toe style for added comfort and durability.

Shop this style:

Vegabond Marja Cap Toe Bootie ($175;

Madewell Regan Boot ($178;

Tony Bianco Bello Boot ($166;

Joules Westbourne Boot ($160;

Coach Nichole Beadchain Chelsea Boots ($225;

Bold, Chunky Welly Boots

These boots are made to stand up to inclement weather, thanks to the rubber material, thick soles, and strong grip, so they are chunky by design. And although unexpected, Levine is a big fan of this trend because it's practical yet playful. Go all out with a colorful boot, as demonstrated on the Prada runway, and pair then with leggings, skinny jeans or a chic skirt, she says. There really are no rules with this one.

Isle Jackobsen RUB 47' Short Waterproof Rain Boot ($215;

Everlane The Rain Boot ($75;

Prada Lug Chelsea Monolith Boot ($850;

Hunter Original Play Tall Boot ($115;

You might also like: 13 Fall Jackets That'll Make You Excited For Cooler Weather

We often receive complimentary products for review at Glam. Each product we feature has been independently selected and reviewed by our editorial team. If you make a purchase using the links included, we may earn a share of the revenue from our affiliate partners.