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How to Wear Men’s Chunky Boots Plus Some Inspiration

How to Wear Men’s Chunky Boots Plus Some Inspiration

After years of slimmer, streamlined silhouettes and dress sneakers, men’s chunky boots have surged forth with the whole Y2K wave. They’ve been spotted on performers at Coachella and on celebrities at the red carpet for the Oscars, and predictably, by fall, they’ll be less of a novelty. 

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Table of Contents

Whether you’re curious about a Cuban heel or like the look of a heavily lugged Chelsea boot, here’s how to try out this trend.

Why We’re Seeing Chunkier Outsoles on Men’s Boots

Bigger, more prominent footwear has been around for the past few years. The dad fashion craze from 2018 onward reworked men’s sneakers through a distorted retro lens.

Whether from Gucci or Balenciaga, the thicker soles, wider cut, and prominent profile inspired by New Balance cross-training shoes was suddenly everywhere and simultaneously borrowed from how middle-aged men have dressed for the past 40 years, with a tinge of irony thrown in. 

man wearing chunky boots

The novelty factor, rather than wear away completely, simply migrated over to boots and other footwear. What has resulted casts a more striking form – part Goth platform boot from the early 2000s, part ‘70s disco king, with hints of ‘90s club kid – and gives standard dress fare a more practical angle.

Fernweh Editions Fern & Petals Candle

What’s so practical about a heavy, chunky heel, you might ask? For one, work and hiking boots have taken this approach for years: Thicker rubber with a more textured, if not lugged, surface creates a stronger, more powerful barrier against the elements and improves traction.

You’re ready to walk through puddles and slush without feeling too much moisture pass through the seam. 

Now, chunky outsoles prove to be an option across all footwear styles, starting with the predictable and extending to and enhancing traditional options. Some deliver a clear heel – thicker and blockier than what you’ll find for women’s footwear – while others ultimately add a flat platform to a more classic shape.

Types of Men’s Chunky Boots and Some Inspiration

Explore different types of men’s chunky boots and how to wear them:

Cuban-Heeled Boots

Perhaps the most obvious place to start, Cuban heels kicked off the men’s high-heel trend with a wider, chunkier design that adds some height without compromising stability. Saint Laurent, under Anthony Vaccarello’s direction, has been pioneering this silhouette over the past few years, usually through a Chelsea boot form in solid black that’s easily paired with skinny jeans.

Carrucci Tokyo Boots

Carrucci Tokyo Boots

Start simple and classic. These boots with a Chelsea-like design appeal to more timeless sensibilities with a smooth leather upper and add more androgynous underpinnings with a pointed toe and more sloped shape. 

Shop on Amazon.com


ASOS DESIGN Cuban Heel Chelsea Boots

ASOS DESIGN Cuban Heel Chelsea Boots

Modern menswear advice tells you to stay away from a square toe. These block-heeled Chelsea boots not only incorporate it to push boundaries of taste but accent it with metal detail around the edge. 

Shop on Asos.com


Our Legacy Black Western Style Boots

Our Legacy Black Western Style Boots

Take a partial cowboy route in these western-styled boots with a wider, thicker block heel, side gussets, and Vibram outsole for comfort. 

Shop on Lyst.com


Chelsea Boots

Although the Cuban heel has made its way onto, if not elevated, the quintessential dress-casual boot, chunkier outsoles provide another alternative – a thicker, more substantial, and somewhat lugged platform that feels borrowed from ‘90s rave style with a bit of effortlessness thrown in. 

Polo Ralph Lauren Bryson Leather Chelsea Boot

Polo Ralph Lauren Bryson Leather Chelsea Boot

Give your look a lift and up its traction factor with these Chelsea boots featuring a smooth, brushed full-grain leather upper exuding classic style and a lugged work boot-inspired outsole. 

Shop on Zappos.com

Fernweh Editions Candles


Burberry Vintage Check Detail Leather Chelsea Boots

Burberry Vintage Check Detail Leather Chelsea Boots

A ridged, almost-spiked outsole draws the eye and gives this classic Chelsea a techier appearance. Burberry’s classic checks further accent the side gusset to up the statement appeal. 

Shop on Lyst.com


Hugo Boss SUEDE CHELSEA BOOTS WITH SEASONAL LOOPS AND CONTRAST WELT

Hugo Boss Suede Chelsea Boots with Seasonal Loops and Contrast Welt

Soft, matte suede starts off with an understated appearance that pulls from heavier-duty, more winter-ready styles with a thicker, more angular lugged outsole.

Shop on Hugoboss.com


Work and Hiking Boots

Consider these the prototype for the current chunky outsole trend, with form and function both placed over fashion.

Crafted for the outdoors, hiking and work boots frequently feature Goodyear welt outsoles given a thicker, lugged construction that improves traction and is less likely to succumb to the elements.

Especially with gorpcore and workwear-inspired styles defining streetwear over the past few years, thicker, rugged outsoles were bound to hit the mainstream. 

Polo Ralph Lauren Alpine Suede Trail Boot

Polo Ralph Lauren Alpine Suede Trail Boot

Old-school hiking boots meant to tackle tough terrain are the inspiration behind this pair, which suits the modern wearer with contrast laces and a thicker, lugged outsole. 

Shop on Modesens.com

Fernweh Editions Candles


Purple Label Fidel Burnished Calfskin Boot

Purple Label Fidel Burnished Calfskin Boot

Starting from trekker inspiration, these boots take you through the city and off the beaten path with burnished calfskin leather, a hand-stitched welt, and Vibram outsole offering a greater degree of traction. 

Shop on Modesens.com


Hugo Boss Hiking-Style Boots in Italian Leather with Shearling Lining

Hugo Boss Hiking-Style Boots in Italian Leather with Shearling Lining

We spot a mix of hiking and workwear inspiration on these boots made with Italian leather and featuring shearling lining for warmth in cold weather. 

Shop on Hugoboss.com


Combat Boots

Thicker, lugged outsoles are a given on a classic combat boot – a military style that’s since made its way into civilian use and influenced how men’s dress boots are designed. More recently, tactical boots – pairing a thicker outsole with overlays for stability and textile for better ventilation – provide a modern and more outdoor-ready upgrade. 

Dr Martens 1460 MEN'S WATERPROOF LACE UP BOOTS

Dr. Martens 1460 Men’s Waterproof Lace-Up Boots

You can’t go wrong with an original. These boots preserve the Dr. Martens silhouette you know while adding DryWair and waterproof welted construction to keep out moisture. 

Shop on Amazon.com


Polo Ralph Lauren Bryson Cap-Toe Leather Boot

Polo Ralph Lauren Bryson Cap-Toe Leather Boot

Shake up expectations for your dress boots. This pair enhances the familiar mid-height, cap-toe design with a prominent chunky lugged outsole. 

Shop on Lyst.com


Stevemadden Guard Black Paint

Steve Madden Guard Black Patent

Patent or tumbled leather with a crinkled appearance commands attention through texture, while zipper details and a thicker, lugged outsole veer away from the typical smooth, polished character. 

Shop on Nordstrom.com


Alexander McQueen Men's Treadslick Chunky-Sole Ankle Combat Boots

Alexander McQueen Men’s Treadslick Chunky-Sole Ankle Combat Boots

The hybrid elements on this boot emerge, through a sneaker-like silhouette accented with a combat boot form and chunky dad shoe-like outsole. 

Shop on Neimanmarcus.com


Moschino Men's Bicolor Stripe Logo Combat Boots

Moschino Men’s Bicolor Stripe Logo Combat Boots

From the striped black-and-white colorway to prominent branding, we wouldn’t expect anything less from Jeremy Scott’s always attention-getting vision. 

Shop on Neimanmarcus.com


Prada Monolith Mini Bag Lug Sole Combat Boot

Prada Monolith Mini Bag Lug Sole Combat Boot

Tactical-inspired elements elevate this boot’s design, while the lugged outsole’s texture creeps onto the exterior for an even techier appearance. 

Shop on Nordstrom.com

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How to Wear Men's Chunky Boots