When I think about winter, I think about darker colors like black and gray.  I really like maroon in the winter and what is better than a warm sweater and a pair of jeans.

Maroon Sweater - Loft - Similar
Black Tank Top - Target - Similar 
Bootcut Jeans - Loft - Similar
Black Flats - Bass Outlet - Similar 
Two Tone Michael Kors Watch - Gift