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How to style boots with jeans Wearing cowboy boots with jeans starts with a general rule of thumb: the jeans should go over your boots and not be tucked in (unless you're tackling heavy- Learn how to wear jeans with boots the right way — and fix the 6 biggest jeans-and-boots mistakes most men over 40 make.
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Full video about cowboy boot modifications here: A good rule of thumb is to make sure your jeans and boots are proportional to one another. This means that the slimmer your jeans are, the sleeker your boots
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