An adaptable and versatile footwear option for fall, this textured leather derby is both rugged and refined. Del Toro's take on the classic derby moccasin boot is handcrafted and stitched by Italian artisans and the quality is noticed immediately. The uppers are constructed from the softest Italian leathers and suedes available, providing a supple, broken-in feel right out of the box. The custom rubber lug sole is thin enough not to distract from the shoe but provide real comfort and maneuverability.

Padmore & Barnes have been synonymous with fine shoemaking for generations, and they've just partnered with Buck Mason on a handsome pair of chukkas for fall. Based on an old pair of American hunting boots, they're cut from an unlined suede and sewn onto a textured rubber sole. Inside, you can feel the craftsmanship and comfort thanks to a reinforced heel cup and cushioned arch support.

This throwback hiker is one of Saucony's most protective styles, combining waterproof GORE-TEX with their proprietary GRID cushioning and XT-900 rubber sole. Just as suitable for rocky trails as they are for rainy sidewalks, they're the kind of sneakers we'll wear with washed jeans, ripstop fatigue pants and even proper trousers for relaxed days at the office.