Cheryl Shops

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. 

Amy Smilovic's Big, Slim, Skin philosophy

I've followed Amy Smilovic, the designer of Tibi, for years on Instagram, and her whole aesthetic is informed by what she calls creative pragmatism. One of the reasons she always looks so cool is that she pays close attention to proportion, or balance, in an outfit. She calls this Big, Slim, Skin and not only is it easy to remember, it's a foolproof way to put together an outfit that just feels right. It's pretty easy to understand: you need one big part, one slim part, and to show some skin—as much as you are comfortable with. As I tried on my shorts a second time with a top that worked proportionally, I realized that Big, Slim, Skin was the way to wear my new shorts without them wearing me. 

The big: shorts

While I've enthusiastically embraced wide-leg jeans, this was my first foray into baggy denim shorts, and as I mentioned, I was a little wary at first. This pair in particular feels very '90s to me—there's an outward curve to the thigh that you don't normally find in cutoffs or any typical pair of shorts, to be honest. The inseam is also a generous 9 inches, which hits me just above the knee. I was worried that these would be stiff being 100% cotton, but they're actually quite soft and the fit is on the relaxed side (they are true to size; I'm in my usual size 6). In other words, they are comfy AF, but that's because they're baggy and, for lack of a better term, big. So to prevent them from veering into big blob territory, balancing the other elements in your look is key. 

The slim: tank top

When I re-tried on the shorts, I happened to have been wearing my favorite lazy weekend tank top—it has a built-in bra, which is the only way I can get away with wearing a cut-in tank like this, because, let's face it, there's no way I'm wearing a strapless bra with a tank top. This was a big unlock for me, because I realized I needed something snug and small to counter the big. I could also have worn my fitted ribbed-knit sweater on top, or a bodysuit, or even a shrunken tee; instead, I chose to layer with a blazer because I didn't want to show too much skin, which brings us to the next step. 

Some skin: the shoes

Because these are shorts, obviously a significant portion of your leg will be exposed when you wear them. Unless it's really hot out and I'm dressing for cooling comfort above anything else, I tend not to expose both my arms and my legs (and to be honest, my arms aren't my favorite feature). So I opted to cover my upper half with a tailored blazer—it's oversized, but it fits me well in the shoulders, so it kind of bridges the gap between the big and the slim—and really play up my legs with a pair of heeled sandals. This pair has a level of sexiness I'm comfortable with (not to mention they're actually comfortable), and the tension they create really works with the big, baggy fit of the shorts and the more masculine, tailored look of the jacket. It's all about the balance—and I think I got it right. 

OUTFIT DETAILS: Uniqlo C blazer (current version) | Uniqlo halter bra tank | Madewell studded belt | Old Navy baggy denim shorts | Inez Isa sandals (use code cheryl15 for 15% off)