A shopping guide for guys—or the women who dress them. Sport jacket (navy or camel hair)
Gray suit (one- or two-button, fitted shoulders, flat-front pants)
Long-sleeved button-down shirts
Crisp white dress shirts
Polo shirts (trim fit and free of embroidered logos)
Gray V-neck cashmere sweater
Khakis (no pleats)
Dark-wash straight-leg jeans (like Levi’s)
Boxer briefs or boxer shorts
Two plain-buckle belts (one black, one wider brown for casual wear)
Classic watch (buy the nicest one you can afford)
Everyday sneakers to wear with jeans, khakis, or cords. Save athletic shoes for when you’re actually working out
Flip-flops
Black lace-up shoes
Chelsea boots (that come above the ankle bone) or brown leather slip-ons (wear only with casual pants)
Outerwear jacket (anorak or windbreaker style) that works for all but the coldest weather