If you read Who What Wear regularly, you’ll know we have a deep and devoted obsession with boots—especially ones that can easily pair with our skinny jeans. There’s no doubt we’ve been sharing some of the chicest boot picks on the market since fall arrived, but we also love to take a deeper dive into what boots you, our dear readers, are buying in abundance.
To get the full picture, we tapped into our commerce strategist for hard data on what styles have been selling like hotcakes on Who What Wear for the past two months. Not surprisingly, black ankle boots have clearly been winning—including classic silhouettes and trending chunky Chelsea and combat boots. Snake-print fabrics have also been super popular with our readers as well as practical waterproof styles that are stylish and protect from the elements. Scroll below as we share the best-selling boots this cold-weather season—in order of the number of units sold—and shop them for yourself.
These might be the most versatile boots you'll own.
Pair with your straight-leg jeans for a practical and cool off-duty look.
Walkable and chic. Win win.
We love the sculptural heel.
Soft suede adds a luxe touch.
Wear with a pleated midi skirt and tie-neck blouse to nail this season's bourgeoisie trend.
Because cowboy boots will never go out of style.
Snake print is your new neutral.
These will amp up even the simplest of outfits.
It's all about chunky Chelsea boots this winter 2019.
And lace-up combat boots!
Wear with literally everything in your closet.
These could pass for designer.
From desk to drinks with ease.
Your savior amidst the winter elements.
So unique.
A rain boot with pizzazz.
You can't go wrong with the price!
Trending hard.
These look way more expensive than the price tag.
Knee-high boots are dominating our feeds right now.
Walk for miles in these minimalist booties.
These are lined with faux fur, people!
Wear them with a cool mini skirt for an of-the-moment look.
Up next, the most beautiful knee-high boots with low heels.
-
If You Love the Row, You’ll Be Obsessed With This Little Known Bag BrandIt very much feels like what a modern day Carolyn Bessette-Kennedy would wear.
-
Cooler Than a White Button-Down: This Specific Shirt Color Is the Key to Looking Chic This FallIt's all over the streets and the spring/summer 2026 runways.
-
Pump the Brakes on Booties—Kate Hudson Knows the Better Fall Shoe Trend to Pair With DressesThis outfit combo is top-tier.
-
7 Expensive-Looking Outfits to Wear With Fall's Most Iconic Shoe TrendLet your outfit do the talking.
-
Forget Lace-Up Boots: This Casual and Easy Boot Trend Is About to Be EverywhereMake this your first boot purchase for the season.
-
The Pretty Dress Trend L.A. It Girls Are Bringing Into Fall (and the "Basic" Style They Already Forgot About)It's finally time to part ways with boring linen dresses.
-
I'm Manifesting a Fashionable Fall in NYC With These 36 Nordstrom Anniversary Sale FindsFrye, AllSaints, Vince, Coach, and more.
-
I Thought Wearing These Shoes With Shorts Was Cringey—Turns Out the Combo Is Peak 2025Apologies are in order.
-
Fall Is Already on My Mind—I'm Prepping My Wardrobe With These 31 Elevated Nordstrom FindsEach piece is chic and on sale.
-
Katie Holmes Is Already Wearing the Boho Boot Color Trend Fashion People Everywhere Will Wear This FallNot once, but twice.
