Cheryl Shops

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.

I've found Agolde's Parker shorts to be super popular amongst many of the influencers I follow, but yikes stripes, $128 seems like a lot for a pair of denim shorts, doesn't it? Granted, I do have one pair of actual cutoff jean shorts—they're from an old pair of bootcut 7 For All Mankind from the early aughts—but the fact that I don't feel super great in them helps make the case for buying a specially constructed pair of shorts. What the Parker and its many imitators have going for them is an angled, very wide leg, which would look more like a '90s raver-style jean if it were full length. I decided on this Madewell pair after seeing them on Grace Atwood, who has a similar body type to me, and whose opinion I trust. These shorts are 100% cotton, which can be terrifying in regular jeans but in shorts is helpful, because it helps them hold their shape  better. They run really big; I went down one size to a 27 and possibly could have gone down one more, to a 26, as mine are still quite large. I found that adding a belt helps them stay in place better and prevent them from shifting around, plus it dresses them up a little. I was a little nervous and self-conscious the first time I wore them out in San Francisco because, let's face it, I'm a 43-year-old woman with spider veins and cellulite. But I wore them two days in a row in Chicago last weekend and they really began to grow on me. They're very practical with sneakers or flats of course, but I've found that my favorite way to wear them is a little dressed up, with a jacket and a heel. Now if only it would warm up enough for me to pull off this combination in San Francisco!

It's been awhile since you've seen this Topshop blazer—a couple years, to be exact, and coincidentally enough, I was also wearing it over a striped tee, with denim. I almost sold it on Poshmark because I was worried that it looked a bit young, but then I decided to stop caring what people might think and just wear what I love instead. It was actually a little cool at times in Chicago, so this linen-blend blazer was the perfect layer. I did wear this blazer over a linen shirt to dinner, but I like it even better with the striped tee because it's just a little more casual. This particular H&M T-shirt is ancient (you last saw it with a slip skirt), but it's a classic and there are a ton of similar styles out there. 

My rule of thumb is that the shorter your skirt, the lower your heel should be. So considering these shorts have barely a 3-inch inseam, in theory I should be wearing them with flats. But I think shorts get a pass on that rule, because I definitely look and feel better with just a little lift. Like the blazer and tee duo, these Hermès sandals (last seen in my honest review) make the shorts look dressier but not too dressy—the low stacked heel and slip-on styling make them feel a little less fussy. For all you ever wanted to know about this shoe (one of my all time faves), check out my review.

As I mentioned earlier, I like wearing these shorts with a belt because they're still a bit big on me, so it helps prevent them from shifting around. I think this Isabel Marant belt (last seen with a coatigan) helps the whole outfit look more polished too. Same goes for my trusty A.P.C. bag; I had initially wanted to bring a more summery bag on my trip but realized that this one just always looks good with everything. Plus, we were staying at The Drake (where we shot these) so I had to at least look somewhat fancy. ;) 

OUTFIT DETAILS: Topshop blazer (similar here; budget version here) | H&M tee (similar here) | Madewell denim shorts | Isabel Marant Lecce belt | Hermes Oasis sandals