Jock-appealing stripes score off the field, too. Jacket, $168, Banana Republic; sweater, $345, Maison Martin Margiela; polo, $29.50, American Eagle Outfitters; jeans, $149, Miss Sixty; headband, $75, Burberry.
GLAM-ORAK: An anorak cropped short has allure to spare.
DENIM SHORTS: A tailored pair with smart wedges lengthens the leg.
Jacket, $118, Arden B; pants, $225, DKNY; shoes, $89, Nine West; headband, $75, Burberry.