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Red Wing and similar brands are having something of a fashion renaissance, despite their relatively utilitarian heritage. This seems to be directly paired with the popularization of skinnier jeans- as the jeans get tighter, the feet get bigger.

Verdict: Go for them, but don't go overboard. One pair of nice Red Wing boots will last forever, and they are almost always made incredibly well- you really can't go wrong. Still, don't over-do them- they can be a bit much for everyday use, and in most countries are still associated with construction workers.

Pictured: Red Wing rugged classic boots ($225)