Fashionable Boots

Eight stylish boots for men that can walk from city to country

A solid pair of work boots will get any dapper dude through the winter months, whether trudging through the snow to a gallery opening or chopping wood in the wilderness. While a classic pair is sure to last year after year, there are a few labels that make a sturdy boot but let fashion lead the way. From the high-end house of Alexander McQueen to heritage legends Woolrich Woolen Mills, the following are eight pairs of boots for the more sartorially inclined man on the move.

Woolrich-mills-boot.jpg Cole-Haan-boots.jpg
Woolrich Woolen Mills

The ultimate heritage-inspired Para boot adds melton wool for a more casual accent to the traditional Derby brogue styling. A pebble-leather upper, stacked sole with Goodyear welt and waxed laces complete the look for €477. Made in England, check Nitty Gritty for details.

Cole Haan

For a more padded option, the Air Jayhawker ankle boot is lined with leather and supported with Nike Air. The heavily burnished suede lace-up takes its distinguished look from the longwing detailing and heavy welt where the upper meets the leather sole. These subtle boots are perfect for those with subtle style. Get them for $298 from the Cole Haan webshop.

Helm-boot.jpg Grenson-boot1.jpg

Helm handmade boots recently partnered with North Carolina-based Raleigh Denim for the new release of their Ray Ray boot. Marking the first time the American-made denim company has allowed their denim to be used by another designer, the boot sports a more tailored toe box with a sophisticated aesthetic. With an Italian crafted sole of Dutch calfskin, the Ray Ray sells for $445 from Helm online.


Also made in England, the Glenn boot is designed to resemble an old Italian infantry boot from the late 1800s. With updated materials and craftsmanship, the Glenn features British Millerain waxed canvas and a leather single sole. Available for £195 online through Grenson.

Rachel-boots.jpg White-boots.jpg
Rachel Comey

Rachel Comey’s Ruger boot resembles those intended for the assembly line, but with a much softer leather and stacked leather sole that is “ideal for a professor of architecture, perfect for a hard day on the instruction site.” The striped leather laces add a nice unfinished look to the glossy black boot, which is available for $403 from the Rachel Comey site.

White’s Boots

Truly American made, the Original Semi-Dress boot is special order only and handcrafted of a five inch mid-weight leather upper. The stitch-down construction shapes the shoe to your foot while the the single layer leather sole continues to add to the personalized fit. Check White’s Boots online, where the Semi-Dress sells for just under $400.

Yohji-boots.jpg McQueen-boots.jpg
Yohji Yamamoto

As definitely the boldest boot in the lineup, Yohji Yamamoto’s Zip Lace Up boot is the quintessential adaptation of military fashion. The dramatic boots are constructed of rich cowhide leather with 15 sets of lace holes, a full-length black metal zipper on the inside of the foot and a thick black Vibram rubber sole. With an intimidating price tag of just over $1,375, the incredibly detailed boots sell online from London’s LN-CC.

Alexander McQueen

Also inspired by military workwear, the Alexander McQueen’s Zip-Placket boot is just as extravagant as one would expect from the revolutionary label. Made in Italy of pebbled leather and a thick lug rubber sole, the eight-eyelet vamp is fastened with a removable zippered leather placket. High fashion comes at a high price, and these McQueen beauties go for $785 from Park & Bond.