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I keep seeing girls wearing Chuck Taylors, or Vans, or even some more modern high-tops, and I always cringe. Sneakers are intended for function, not form; they aren't attractive. Unless they are paired with athletic clothes (i.e. for the gym or running) they look clunky or awkward. The fact that they are "comfortable" or "quirky" or "classics" might be perfectly true, in some cases might be a good reason for wearing them; but don't fool yourself into thinking they make you look good. While it would obviously be unrealistic and probably unhealthy for women to wear high heels every day, there are many more elegant compromises than sneakers.

If you see a woman who you think is more attractive because she is wearing sneakers, ask yourself whether it is because of them or in spite of them. You'd be better off never wearing sneakers than trying to pull them off.