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. (; available at

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. (; available at

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. (, available at


“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. (, available at

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. (, available at

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