I LOVE cowboy boots and I think they have the potential to look really cute with dresses, but this look has to be done right. Above, I featured two pictures, a hit and a miss. Although I personally like Hillary Duff (left) more than Taylor Swift (right) I have to agree that Taylor wears this look right. Hillary's dress is just too short, and the style does not really "match" the boots. Taylor, on the other hand, wears her flirty spring/summer dress with boots that "match" the dress. Sorry Hillary, this is a miss. Taylor takes this one.
Generally when wearing boots with a dress you want to choose a dress that is flowy and casual. Your dress should hit right above the knee (don't go to short like Hillary) and you should still be able to see skin between the top of the boot and your knee, I think Hillary's boots are just a little too tall for her.
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