I have to confess that I am ambivalent about shorts. I understand their utility, but I always wind up feeling like throwing on a pair of shorts is the equivalent of giving up, like I could wear something cuter if I would just try a little harder. But there are times — baseball season, say, or August — where shorts are the most appropriate option for my life.
The trick to making even the most casual shorts look stylish is really in what you wear with them. My shorts wardrobe (all two pairs) are basic chinos — durable, versatile, machine washable. I have no illusions about dressing them up (in fact, I’m not a fan of “dressy” shorts, or of shorts for the office — shorts are for casual wear, period). But I do want my shorts to be flattering, and I do not want to look like I just came from cleaning out the garage when I leave the house in shorts.
I assume you feel the same way about your shorts. So what do you wear them with?
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