Gentlemen, I’m seeking a bit of sartorial counsel for an upcoming all-inclusive resort trip to Cancun. As much as I’d enjoy bringing half my closet, I’m attempting to exercise some uncommon restraint and limit myself to three pairs of shoes, plus whatever pair earns the privilege of accompanying me on the flight. My current contenders are: A) Brown driving loafers B) Navy suede espadrilles C) Brown suede loafers D) Leather sandals The wardrobe will consist primarily of linen shirts, polos, lightweight trousers, and the occasional linen jacket for dinner. Think relaxed resort elegance rather than “spring break survivor.” My concern is whether I’m being unnecessarily redundant with both the driving loafers and suede loafers, or whether each earns its place in the rotation. Likewise, are the navy suede espadrilles a resort essential, or merely my latest attempt to justify another shoe purchase? If you were limited to three pairs, which would make the final cut—and which would be left standing sadly by the closet door as I head for the airport? Looking forward to your thoughts, disagreements, and inevitable recommendations that I buy another pair entirely. #thestruggleisreal