Wear a pair that hits just below the knee with tights and a skirt for a feminine cold-weather look, or pair them with leggings and a long cardigan for cozy sophistication. We love these Frye Paige Tall Riding Boots for a classic yet trendy look.
Other riding boots we love — under $100:
- Park Lane Buckle Riding Boots ($53.79)
- Steve Madden Tsunamii ($80)
- Miss Mooz Hugo ($89.97)
Up next: More classic fashion styles >>
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