Top a peacoat with this ear-covering, 1920s-inspired angora-blend cloche.
Nine West, $38; Macys.com


A beret is always très chic—especially in a print and neutral colors.
Mark, $15; MeetMark.com


This ribbed alpaca turban frames the face without overpowering it.
Eugenia Kim, $77; RevolveClothing.com


Metallic and faux-pearl embellishment dresses up this sporty mohair-blend cap.
$49; Talbots.com

Next: How to organize your winter closet

From the January 2011 issue of O, The Oprah Magazine