Five Classic Shoes Every Gentleman Needs in His Wardrobe

The search for the perfect shoes may seem endless, but according to Steven Taffel—founder and owner of Leffot, the celebrated multi-brand men’s shoe store in Manhattan’s West Village—there is a key factor that can aid in decision making: Instead of focusing on what’s in, seek classic styling of the highest quality. “Trends come and go,” explains Taffel, whose store offers a handpicked selection of the latest high-end and made-to-order footwear by leading shoemakers from around the globe. “I stay away from trends, and instead follow subtle changes, such as the shape of the last (the mold used to make shoes) or the cut of the waist. These simple changes give the shoe and foot an elegant and flattering appearance.”

We asked Taffel—who worked in the fashion industry for over 30 years before opening Leffot in 2008—to shed light on the must-have classic styles for men’s formal and informal needs. The following are five essential shoes for every gentleman. (leffot.com)

A dress shoe that is ideal for business, the cap-toe oxford will forever be a classic. “A cap-toe oxford is a simple lace-up with a ‘cap’ sewn across the toe portion,” describes Taffel, who suggests the black calfskin leather style with oak-bark soles offered by Savile Row’s Gaziano & Girling ($1,300). An updated shape, featuring a narrow waist and a long toe box, differentiate the shoes, which are handcrafted in England. (gazianogirling.com; available at leffot.com)

Another must-have lace-up shoe—this one quintessentially American—is the wing-tip brogue, which features a wing design on the toe, explains Taffel. “Brogue refers to punching and gimping elements.” He recommends the cordovan long-wing blucher by Alden ($702). The 132-year-old shoemaker uses cordovan tanned by Chicago’s Horween Leather Company to achieve the rich, deep eggplant hue. (aldenshop.com; available at leffot.com)

The split-toe derby is another staple for the wardrobe. “A derby is a lace-up that has open lacing quarters,” says Taffel. “And split-toe is a seam that runs down the toe of the shoe.” Edward Green offers a sophisticated iteration of the comfortable, everyday shoe: the Dover ($1,415). Handcrafted at the company’s atelier in Northampton, England, each pair features a vamp that is sewn using a pig’s bristle instead of a needle—a swap that aids in the delicacy of the task. As with all Edward Green shoes, the Dover can be made to order. (edwardgreen.com, available at leffot.com)

“These days, I wear Edward Green shoes most of the time,” admits Taffel, but he also recommends the 126-year-old brand’s Galway boot (from $1,238). “I find the classic English style to be timeless, and the quality, attention to detail, and fit are all excellent.” A refined take on the classically rugged footwear, the handmade paneled boot (also available made-to-order) is offered in a range of colors and materials, including calfskin and suede. (edwardgreen.com, available at leffot.com)

The always-comfortable slip-on shoe without laces—the loafer—is another footwear essential, according to Taffel, who suggests penny loafers from the Austrian shoemaker Saint Crispin’s ($1,510). With sturdy soles handcrafted in calfskin—the dark brown shoes are just as stylish with jeans as they are with a tailored suit. (saintcrispins.com, available at leffot.com)

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