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An extension of this look that might work would be non-ripped leggings, cowboy boots and a tunic dress and cardigan. Go simple and white like Ashley Olsen or Jessica Alba, or for a more extreme look, pair boots with a colorful dress like Miley. This way of wearing cowboy boots is my favorite of all! Please help, How do I wear cowboy boots? They make a statement on their own, so let them be the focus! There are two ways to do this, and which one you pick depends on your personal style and which type of jeans you prefer! Cowboy boots are better as a once-in-a-while thing.

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The above photo of Mary Kate Olsen circa was the best picture I could find of someone rocking cowboy boots with leggings.

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I think their dresses would go perfectly with cowboy boots! The above photo of Mary Kate Olsen circa was the best picture I could find of someone rocking cowboy boots with leggings. Feel free to improvise with your own and be creative in your outfit choices!

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