There are many things I love about a chunky boot—practically and aesthetically. (As I learned first and foremost last weekend: cowboy boots and icy gutters can result in catastrophes fully preventable by lug soles.) In a chunky boot, I get the height I desire and the stability I need—I can stomp around Brooklyn at an artificial 5’9” and not involuntarily ice skate to my front door. Here, I’ve rounded up four ways to wear chunky boots for various occasions and moods so that you, too, may trudge through winter weather with warmth, security, and style.
Long Sweater Dress + Distressed Leather Jacket
Photo: Christian Vierig/Getty Images
I love contrasting a chunky boot and boxy jacket with a fitted dress. Balancing the heaviness of those shapes—without sacrificing warmth—is a challenge, and this is a reliable go-to formula.
Canadian Tuxedo + Leather Trench
Photo: Melodie Jeng/Getty Images
I have always found Canadian tuxedos chic in a Badlands kind of way. With the right wash and fit, you have unlimited styling possibilities; one of my favorites being with a classic fitted tee, leather trench, and vaguely cybergoth platform boots.
Suit Separates + High Slit Skirt
Photo: Claudio Lavenia/Getty Images
A good way to get out of a styling rut is to place classic pieces (a blazer, a sweater vest, a button-up) in an unconventional context. In this case, details associated with men's formalwear are remixed and yass-ified when paired with a high-slit skirt and calf-hugging, knee-high boots.
Military Jacket + Layered Button Down + Relaxed Lightwash Denim
Photo: Edward Berthelot/Getty Images
Of the indie sleaze fashion hits that may (or may not) be returning to my sartorial vocabulary, ‘military jacket’ was not one on my bingo card. I was too focused on disco pants and zip-up hoodies to consider the Julian Casablancas classic, but this look made me realize my oversight. A military jacket styled with loose, straight-leg denim, an open button-up, and white lug-sole Chelsea boots is the perfect combination of structured and relaxed—effortless and intentional.
