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19 Chunky Boots Outfits to Try This Fall/Winter Season

By

Nicolette Baker

Published on 11/22/23 07:00AM

Close-up of woman pulling on studded chunky boots while wearing a leather jacket and shirt dress — @dolcevita / Instagram

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

Hailey Bieber wears a structured black coat, skinny rectangle sunglasses, chunky black puffer boots, and leather pants — Getty Images

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.

The North Face Nuptse Apres Booties in black and gray

The North Face Nuptse Après Booties $109.00

Star-Studded

Close-up of woman adjusting studded chunky sole boots while wearing leather jacket and shirt dress — @dolcevita / Instagram

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.

Dolce Vita Hoven Stud H2O Waterproof Chelsea Boots in black studded leather

Dolce Vita Hoven Stud H2O Waterproof Chelsea Boot $180.00 $85.00

Sky-High

Rita Ora wears a pinstriped blazer, black micro shorts, thigh-high socks, and chunky black boots with chain detail — Getty Images

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.

London Rag Axle Boot with chunky sole in black

London Rag Axle Boot $80.00 $70.00

Buckle Up

Olivia Rodrigo wears a plaid mini dress, layered necklaces, and strappy knee-high chunky boots — @oliviarodrigo / Instagram

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.

Lamoda Platform Shoe with High Leg Fastening in black

Lamoda Platform Shoe with High Leg Fastening $122.00 $32.00

In Full Bloom

Heidi Klum wears a yellow floral mini dress and black over-the-knee boots — Getty Images

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.

Kurt Geiger Trekker Sock Knee-High Boots

Kurt Geiger Trekker Sock Knee-High Boots $210.00

Wintry Wonder

Storm Reid wears a full Prada look including a puffer coat, catsuit, white handbag, and snow boots — @stormreid / Instagram

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.

Pajar Vantage Boot in black

Pajar Vantage Boot $245.00

Streamlined Soles

Taylor Swift wears a black tank top, wide leg pants, tan baseball cap, and chunky boots with streamlined soles — Getty Images

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.

Everlane The Puffa Boot in black

Everlane The Puffa Boot $285.00

Stitched Style

Madison Bailey wears a denim jacket, corseted top, light wash shorts, and black chunky boots — @madisonbaileybabe / Instagram

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.

Steve Madden Bettyy Boots

Steve Madden Bettyy $100.00

Cozy Platforms

Bella Hadid wears mini Ugg boots, white crew socks, an oversized leather jacket, graphic tee, and shield sunglasses — Getty Images

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.

Ugg Classic Mini Platform in chestnut

Ugg Classic Mini Platform $170.00

Bikercore

Yara Shahidi wears a khaki cape top, pleated mini skirt, bike shorts, and black chunky motorcycle boots — @yarashahidi / Instagram

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.

Frye Veronica Leather Buckle Short Moto Boots in black

Frye Veronica Leather Buckle Short Moto Boots $298.00

Square-Toe Chic

Sabrina Carpenter wears a white button-down shirt, denim Bermuda shorts, square-toe knee-high chunky boots, a black shoulder bag, and glasses — @sabrinacarpenter / Instagram

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.

Sunni Sunni Reese Leather Boots in black

Sunni Sunni Reese Leather Boots $980.00

Pretty in Platforms

Toni Bravo wears a silver sequined top, black maxi skirt, platform boots, slouchy handbag, and layered jewelry — @bonitravo / Instagram

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.

Steve Madden Klayton black platform boots

Steve Madden Klayton $100.00

Unexpected Hues

Petra van Bremen wears a sheer floral maxi dress, chunky white lace-up boots, sunglasses, and a tan handbag — Getty Images

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.

Nine West Forme Chelsea Lug Sole Boots in cream

Nine West Forme Chelsea Lug Sole Boots $139.00

Sleek Snakeskin

Megan Fox wears a green, blue, and black striped cardigan, white button-down shirt dress, and black snakeskin boots — @meganfox / Instagram

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.

Sunni Sunni Reese Snake-Embossed Boots in brown snakeskin

Sunni Sunni Reese Snake-Embossed Boots $940.00

High Contrast

Abby Bible wears a patchwork coat, jeans, cream boots with chunky black soles, and houndstooth bucket hat — @theabbybible / Instagram

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.

Timberland Everleigh Chelsea Boot in light yellow nubuck with black chunky soles

Timberland Everleigh Chelsea Boot $160.00

Tough Luck

Emily Ratajkowski wears a white cropped tank, wide leg jeans, and Timberland boots — Getty Images

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.

Kendall Miles Ali Combat Boots in camel

Kendall Miles Ali Combat Boots $695.00

Golden Glimmer

Lulu Wang wears a pink puff-sleeved dress, black structured handbag, and black chunky boots with gold detailing — Getty Images

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.

Coach Kenna Leather Bootie in black

Coach Kenna Leather Bootie $325.00 $195.00

Get Graphic

Paloma Elsesser wears a white "Holy" graphic tank, black midi skirt, and Chanel rain boots — @palomija / Instagram

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.

Anine Bing Kari Rain Boots $250.00

Pop of Color

Ice Spice wearing black cropped long-sleeve shirt, black sweatpants, patterned handbag, and yellow rubber chunky boots — @icespice / Instagram

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.

Moncler Ginette Rain Boot in yellow

Moncler Ginette Rain Boot $465.00

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