When I think of a fall/winter dressy heel, this fits the bill. It's strappy, yet thick, and the color is great for the season. The solid heel looks best with long, layered winter clothes. Though it's for cold weather, we still get to see some foot and fresh pedicures (year round for us ladies). This Derek Lam Penelope Perforated Sandal would look great with a DVF wrap dress or a way to dress up jeans. The heel is 4.25", available at eLuxuryry. $895