19 Chunky Boots Outfits to Try This Fall/Winter Season (2024)

We’ll say it: Chunky boots are one of the most versatile staples in our closets. Bold and attention-grabbing, this footwear offers far more than just a thick tread and statement details. The chunky boots silhouette—which entered the mainstream alongside the ‘90s grunge wave—shares a distinct dose of attitude. Depending on the styling, your boots of choice can create balance in a structured ensemble or add punk-rock edginess to a playful maxi dress. Below, discover 19 chunky boots outfit ideas as seen on celebrities, complete with some of our favorite shoe picks of the season.

Bundled Up

Whether embracing the après ski life or simply strutting to work, we highly recommend stepping into winter by wearing some ever-trendy puffer boots. Mix-and-match textures are the name of the game this season, so pair your chunky boots with sleek leather leggings and a wool coat.

Star-Studded

An edgy take on the classic Chelsea shape, these chunky boots offer a bit of glitz with generous helping of toughness. Try pairing them with sheer tights and a mini skirt (or perhaps a skort) to transition into fall.

Sky-High

Riding boots are definitely having a moment as horse girl style continues to trend, so feel free to indulge in a thick-soled pair that hits mid-calf. Coordinating thigh-high socks emphasize the drama, while cool silver details can add a bit of shine.

Buckle Up

These are statement shoes if we’ve ever seen them. Olivia Rodrigo offered up some major chunky boots inspiration when she paired massive punk-inspired platforms with a nostalgic plaid mini dress. Don’t forget to wear sunscreen if you’re stepping outside, though—otherwise, prepare for ultra-bold tan lines.

In Full Bloom

A dramatic pair of chunky boots is an easy way to contrast a floral dress or A-line skirt, as Heidi Klum exemplifies here. This version, from British luxury brand Kurt Geiger, hits just below the knee and offers a thick tread.

Wintry Wonder

Who said snow gear can't be stylish? A chunky black pair of snow boots has so many styling possibilities, and Storm Reid looked extra cool when she paired hers with a jumpsuit, cropped puffer, and white handbag.

Streamlined Soles

If we raided Taylor Swift’s shoe closet circa 2015, it’s more than likely we’d encounter several pairs of Chelsea boots. Take notes from the 12-time Grammy winner—who continues to embrace the timeless style to this day—and select a sleek, tread-less sole for maximum impact.

Stitched Style

Contrast stitching on the sole is a fun way to bring an artsy energy to chunky combat boots. Lean into the cool-girl-next-door energy by pairing them with a multi-toned denim ensemble, as Madison Bailey does here.

Cozy Platforms

Bella Hadid nearly broke the internet when she emerged in chunky Ugg boots last year, and we're still thinking about copying her look today. When combined with a color-blocked leather jacket and white tube socks, this outfit exudes “model-off-duty” style at its coziest.

Bikercore

Motorcycle boots are back in a major way this season, and we love them for their worn-in charm and tough silver details. We’d consider this the ideal footwear to pair with all-black ensembles or structured neutral pieces.

Square-Toe Chic

This glossy style falls on the sweeter end of the chunky boots scale. While high-quality patent leather can be an investment, rest assured that the sophisticated look (and countless styling options) is completely worth it.

Pretty in Platforms

Platform boots are the epitome of chunky footwear, taking the standard heel height and dialing it up to the max. These sky-high kicks combine a sturdy platform with a dramatic silhouette that’s absolutely primed for a night out.

Unexpected Hues

While you’ll typically discover chunky boots in a range of black, brown, and rust shades, there’s no reason to overlook lighter varieties. Take this pair of cream chunky boots as a fresh iteration of the cold-weather staple.

Sleek Snakeskin

Eclectic and somewhat intimidating, snakeskin is a step up from your typical chunky platform. Try this trend in a glossy black or brown, then pair it with an unexpectedly preppy skirt.

High Contrast

These two-tone boots combine a bold color combo with classic details for a high-drama look. Pair them with your favorite denim and a sweet quilt-inspired jacket, or even hiking gear—these all-terrain (yet stylish) boots can do it all.

Tough Luck

Lace-up combat boots—known for their wide availability in a variety of colors and price points—are often a go-to for edgy footwear. Choose a camel-colored pair to complement an otherwise monochromatic look, and let this chunky boots style shine.

Golden Glimmer

Gold hardware adds a bit of charm to otherwise rough-around-the-edges footwear. Lean into that softness with a puff-sleeved dress or a velvety, oversized sweater and satin maxi skirt.

Get Graphic

A logo is a great way to turn otherwise understated rain boots into a bolder moment, and we love how Paloma Elsesser combined hers with a graphic tank and two-toned midi skirt. Sticking to a common color scheme is a straightforward way to keep the look cohesive.

Pop of Color

Chunky boots' dramatic soles already make them the stars of the show, so lean into that energy by choosing a pair in a statement color. Follow Ice Spice's lead and pair a sunny yellow style with your favorite black sweatpants and a patterned handbag.