Photo: Martin Poole/Thinkstock

Sport jacket (navy or camel hair)

Gray suit (one- or two-button, fitted shoulders, flat-front pants)

Long-sleeved button-down shirts (J.Crew is good)

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 (we 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 (Stan Smith, Rod Laver) to wear with jeans, khakis, or cords. Save athletic shoes for when you're actually working out

Flip-flops (surfer style from Reef)

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


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