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Q&A:
What should I wear with a classic riding boot?
Riding boots are a great staple to have in your wardrobe as they are both comfortable and timeless. Typically worn on the outside of a slim pant, they create a clean, elegant look. Be sure to have a pair of jeans and a trouser with a slim ankle as they will slide into the boot easier and more comfortably. Alternatively, pair a riding boot with wool tights, a lean pencil skirt and an oxford or, on the weekends, with a pair of wool shorts and a cozy knit sweater.
Read more at RL Style Guide