JCPenney Boots $20

These women's boots drop from as much as $85 to $19.99 at JCPenney.com. Shipping adds $8.95 or is free with your purchase of $49 or more. Choose from around 15 styles, including the pictured St. John's Bay Winterwood Riding Boots. Similar styles sell for around $20 more per pair, and this matches the Black Friday and Cyber Monday price.