I am going to be honest with you: denim shorts are one of those things I have a love/hate with. When it works, it works and I feel young and cool and casual. When it doesn’t I feel like an old lady who didn’t look in the mirror before she walked out the door and looks like a moron. There is an art to knowing how to wear denim shorts (always size up!!!) when you’re at a certain age, so you still feel appropriate. Now that’s not to say that we don’t look hot over 40. I’ll tell you right now I feel better about how I look at 46 than I did when I was 36, or even 30. In fact, I wear more denim shorts now than I did back then. But it’s also because I found pairs that work for me and look good. So I’m going to right to it and sharing my favorites.
My all-time favorite pair are these. I sized up a full size (normally I’m a 27 and have these in a 28). This makes them a touch looser and can wear them a little lower on the hip - they also give a little extra space on the thighs. There is nothing less attractive IMHO than jeans shorts that look more like denim bicycle shorts. Vile. I have since purchased them in other washes and colors.