This Sharp New Automatic Watch From Steven Alan Will Only Set You Back $385

Classic and good looking.
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This makes us break our "don't wear a watch from a company that also makes clothes" rule. Steven Alan, makers of some of the best shirts money can buy, just dropped a beautiful automatic watch that's all kinds of simple and cool. Quality wise, it won't compete with an Omega or Rolex, but for under $400, this is a solid substitute and entry-level option.