30. The Wind Breaker — Unfortunately, wind chill is not going away, no matter the time of year, so we say you should beat Zeus at his own game with a wind-breaker that's spare enough to wear with something a lil' dressy, but also able to do double-duty for everyday breezy situations.

Sandro Wind Navy Windbreaker, $515, available at Sandro; Topman Red Polka Dot Print Bomber Jacket, $120, available at Topman.