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Choose between a classic pair of knee-high riding boots or a daring pair of fitted over-the-knee suede boots. Wear some tights or add a pair of cozy knit socks to your riding boots for extra warmth.  Let the tops of the socks peek out above the boots for a cozy, layered look. For example, you could pair some charcoal suede over-the-knee boots with a black fitted turtleneck and a burgundy sleeveless dress. These shoes are a popular fall staple, perfect for pairing with any length of dress, from summer dresses to maxi dresses. Choose a sleek leather pair for instant class or a pair in suede for a soft, autumnal texture. For example, you could wear a rust-colored T-shirt dress with a chunky cream-colored cardigan and some tan leather ankle boots. Pairing your summer dresses with pumps instead of sandals will help you stay warm, chic, and fall-appropriate. Go for a pair in a neutral shade, such as black, navy, or taupe, and choose a pair of opaque tights that matches. For example, you could wear a patterned, burgundy summer dress with some black tights and a pair of black pumps. Add a warm gray blazer to finish off the look.

Summary:
Go with a pair of tall boots to stay warm and chic. Opt for a classic pair of ankle boots for style and versatility. Trade in your summer sandals for a pair of heels to wear with dresses.