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[quote=Anonymous]Are you looking for flat riding-style boots or boots with a thinner, dressier heel? I have both types from Cole Haan and love them both but wear them differently.

The riding boots I wear mostly with pants (cords, jeans, black pants) tucked in. I also wear them with leggings and sweater dresses. If I wore longer / midi skirts, I would wear them with skirts, too. I got them for ~$200 from Zappos about two summers ago. You might find good deals on last year's designs.

The others have a 1.5-2" heel and were probably about $200 from Nordstrom's almost ten years ago. I wear these with knee-length skirts and dresses all winter. I have worn them under jeans when traveling, but have never tucked jeans into them. I'm not a fan of jeans tucked into these types of boots though.

As a PP mentioned, make sure they fit you properly in the shaft width. If you wear them with tights or leggings, you should be able to slide only one or two fingers in the top. That can make it tricky to wear the same pair for both tights and jeans, unless the jeans are practically jeggings or are worn outside the boot.[/quote]

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