You can't even begin to think about winter fashion without thinking about boots—they go together like bread and butter. And this year, there seems to be one style that has stolen the hearts of fashion girls everywhere: chunky boots. I've seen a variety of different takes on the trend; however, Dr. Martens is the brand that will forever reign supreme. Whether you’re into its classic all-black lace-ups (my personal favorites) or digging a more colorful option, there’s no denying that these boots make an outfit look super stylish. Plus, a select few of the brand’s newer shoes include features like faux fur and its innovative WinterGrip soles, making them perfect for the cold weather. Intrigued? Keep scrolling for 16 cute pairs you can wear with any winter fashion look, from your favorite midi dress to your go-to skinny jeans.
Shop all-black booties:
Shop more colors:
-
Better Than Sneakers—the Shoe Trend Women in Their 40s Are Wearing With Jeans at the Cannes AirportThe best airport for style-watching.
-
Sorry, Sandals—*This* Is the Shoe Trend Chic Girls in Their 20s Are Wearing With Dresses in 2026Let Olivia Rodrigo show you the way.
-
J.Lo Just Wore the Rich Boot Color Trend That Makes Floral Dresses Look Stylish (Not Basic)Spotted in L.A.
-
*Not* Sandals—the Anti-Spring Shoe Trend Every Chic Dresser in Milan Is Wearing With Light-Wash JeansUnexpected but practical.
-
I Spent Months Hunting for the Best Black Ankle Boots—7 I'm Putting My Money BehindThese boots are meant for walking.
-
There's One Shoe Style That Looks Best With Miniskirts, and I Have Visual ProofLook edgy with it.
-
Margot Robbie Just Wore the Game-Day Outfit Every College Student LovesOf course, she looks chic.
-
Not Sneakers, Not Flats—People With Good Style Are Wearing Skirts With This Unexpected Shoe Trend InsteadCool Gen Zers already know this one.
