Best Bet: Rachel Comey’s Thistle Booties

Rachel Comey's wood-soled shoes are a rare fashion commodity: high style but still comfortable enough for hoofing it around the city. Unfortunately, they also tend to be splurgey, with price tags regularly topping $400. These Thistle booties are a full 70 percent off at Creatures of Comfort's winter sale. The light wood heels offer an eye-catching contrast, while the black and brown wool-and-suede uppers can complement the bulk of your winter wardrobe.

Rachel Comey Thistle Bootie, $103.50 (originally $345) at Creatures of Comfort and online.