I have never been a big shorts person, although I did wear them a bit more when I was younger. It has always seemed just as easy to wear a dress, which has the added benefit of making it look like you tried a bit harder. But the main reason I tend to stay away from shorts is that they tend to fit me oddly and get all bunched up in front. I blame this on my body's perplexing combination of narrow hips and meaty thighs, which feel more or less equalized in a full or A-line skirt. But in the last few years, I've noticed more and more of my summertime Instagram feed filling up with all manner of shorts but primarily those of the cutoff denim variety. Add in one very long, very casual-izing pandemic plus a summer that's already been ridiculously hot and now it seems like literally everyone is in shorts. But there's more to it than an "everyone else is doing it, so I will too" mindset—I think that in this unprecedented (and welcome) age of body positivity, people are caring less about having "perfect" legs and instead focusing on wearing whatever they want, for whatever reason they want. So that's what convinced me to buy my first pair of shorts in 20 years. Here's how I wore them in Chicago last weekend.
