Don't put Nike's windbreaker atop your date night fit, if wearing dress shoes and a button-down. A foolproof formula: tee (or short-sleeve polo), khaki or linen shorts, loafers, jacket.
For something even more casual: tee (or tank), casual shorts, sneakers, jacket. These jackets are so lightweight, ideal for layering in fall and winter by pairing with heavier coats or sweaters.
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