Boots with Sole

Rodd & Gunn_TAUPE_F-featureWhether this winter’s plans involve scaling a mountain or braving the city streets, a sturdy pair of boots is the foundation of any man’s cold-weather wardrobe.

Stylist Sarah Schussheim, who has worked with celebrities including Ashton Kutcher and Chris Pratt, suggests investing in “one polished pair and one rough-and-tumble style [of boot] that improves with time.” One of Schussheim’s suggestions is the classic Chelsea boot—both Common Projects and R.M. Williams boast timeless styles. Another option is a laced boot rendered in suede, nubuck or leather, as seen in Rodd & Gunn and Oak Street Bootmakers collections.

As far as color is concerned, Schussheim says you can’t go wrong with “anything brown, from a tan to a camel to a cigar, or a somber gray,” as the neutral colors go easily with everything from jeans to chinos. To complete the look, it’s all about combining the right pieces: A suede hiking boot goes well with raw denim to accomplish a polished, off-duty style, while a sharp leather boot paired with a suit makes a smart replacement for the classic brogue. Live in a cold climate or traveling to one? A sturdy pair of Quoddy Perry boots and a puffer jacket have you covered. This winter, it’s easier than ever to put your best foot forward.

  • The Quoddy Perry Boot, available in several different colors, is handmade in Maine. This timeless style will only improve with age, $450, at

  • The muted charcoal shade and crepe sole of the Common Projects Suede Chelsea Boot makes it a closet staple, $530, at

  • Rodd & Gunn’s Barber Road Boot is an ideal option for the boot novice thanks to a slim silhouette and minimal detailing, $198, available at all Montage boutiques.

  • The Oak Street Bootmakers Natural Rough-Out Dainite Trench Boot is rendered in refined suede, making everything from a pair of jeans to a suit look especially dapper, $468, at

  • The R.M. Williams Dynamic Flex Craftsman Chelsea boots come in a range of colors and can handle anything you throw at them, price varies, at

By Nicky Deam