I remember my first pair of denim shorts. I had just seen Dirty Dancing and was obsessed with the pair that Jennifer Grey wore as Baby. Like hers, mine were long and fitted almost to the knee with a rolled cuff. I wore them religiously until they didn't fit anymore, and while I have owned many denim shorts since then, I haven't loved any of them as much as that first pair. While I was very into them at first, I don't find myself reaching for the Madewell shorts I bought a few years back and as the years pass, I'm feeling more wary of shorter shorts. That said, I do enjoy shorts as an option when the weather is warm, and as a denim lover, I'm always up for an alternative to longer jeans. I was influenced to buy a pair of uncharacteristically (for me) baggy denim shorts from Old Navy—I sadly can't remember which Substack newsletter had recommended them—and when I first tried them on, I thought these are not for me. But then on a warm Saturday afternoon when I just wanted to be cool and comfortable, I decided to give them another try. This time I was wearing a slim-fitting tank top and all of a sudden it came together: You can wear baggy denim shorts without looking sloppy. It's just a matter of getting the proportions right.
