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Interesting. I've seen people, usually younger men, cuff their jeans on purpose, and while I don't like the look, I don't think there's anything inherently wrong with it.
Sometimes I have to cuff my new jeans about a half-inch or so, especially around the house when I'm not wearing shoes, because I don't want the edges to get worn down. I tend to buy my jeans slightly long so they get what is called "stacking" (crumple considerably) above the shoe. Since mine are the straight and tapered kind, even longish they usually don't drag under the shoe but rather stack above it.
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Ever notice how this place just basically, well, sucks.
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