HOW TO WEAR: Roll chinos to just above your shoes, then finish with a lightweight knit tank or sweater.
WHAT TO AVOID: Fitted midlength skirts—their tight shape with ankle boots will make calves seem chunky.
SHOP THE LOOK: (clockwise from top) Leather, Nine West, $89; ninewest.com. Leather with brass studs, Charles by Charles David, $175; 310-659-7110. Silk and perch, Proenza Schouler, $930; 310-652-1120. Python, Alexandre Birman, $445; bergdorfgoodman.com.Read MoreLess