Crosby Boot — Brown

The Crosby is a clas­sic three-eyelet chukka boot with a moccasin toe. Made in soft, supple suede on crepe soles, they’re easy to wear with soft, casual tail­or­ing or jeans and a roll­neck sweater. As Drake’s creat­ive director Michael Hill says, “If you’re trav­el­ling and can only take one pair of shoes, take these.”