Is A Good Pair of Shorts the Hardest Thing to Find?
On finding styles I actually like, after years of experimenting.
When I was a kid, a pair of shorts was a big part of my summer uniform. I’d chuck them on with a T-shirt, pull them on over my cossie after a day at the beach, and think I was at the height of fashion when pairing them with a halterneck that had daisies appliqued along the neckline (fellow ‘90s Brit kids will know Tammy Girl was where it was at).
But then over the years, my shorts collection dwindled. Aside from the denim cut-offs with the pockets hanging out look I wore all summer long in my late teens/early ‘20s, shorts became much less of a go-to. I’d always pack a pair on holiday but only as a casual practical option. They were something I’d pull on before leaving my bedroom for breakfast or shove into a beach bag. But going out for dinner or a nice little day trip? Shorts wouldn’t get a look in, it was dresses only.
That didn’t stop me from always looking at shorts though, trying them on or hastily buying a new pair online because I still had this notion that shorts = summer. But I’d always end up feeling a bit deflated. Nothing looked quite right. I felt the long, tailored shorts that looked great on others were frumpy on me. Cycling shorts didn’t make me look like Princess Diana, they just dug into my thighs. And, I’ll be honest, I didn’t like that the cellulite on the back of my thighs could be seen whenever I wore short shorts.
I’m not the first woman to have an issue with shorts and I know I won’t be the last. I reached out to my fellow Substackers on Notes to get their thoughts, and, well, the replies said it all. Most WANTED to like them but struggled to find styles they felt good in and complemented their body shape. The other recurring theme was the struggle of styling the shorts. While some like
, , and had found their go-to style and had very specific criteria when buying a pair of shorts. This is the camp that I now find myself in.Finding a style I feel good in
After years of experimenting, last summer I finally found a style that clicked. It was a pair of navy striped boxer shorts that formed part of a collaboration between Collagerie and With Nothing Underneath. When they first arrived at my door, my initial reaction was: “They’re too short. I’ll have to send them back.” But I tried them on anyway and… reader, I loved them.
They sat high (ish) on the waist. They were beautifully cut. The fabric felt soft and comfortable. They were slightly loose on the leg so they didn’t cling, and they fit neatly on the waist without that weird bunching you sometimes get when there’s too much fabric.
Huh. Maybe short (ish) shorts were the ones all along.
Since then, I’ve added a few more shorts to my wardrobe, all in a similar style. And for the first time in decades, I genuinely enjoy wearing shorts out and about.
How to find a style that works for you
First, experiment with different styles. If you struggle with shorts but want to wear them, the best thing that I can say is to throw your preconceptions out of the window and try every style you can. You might be surprised at what you do end up liking.
Try shorts made from good quality fabric. This makes a huge difference because they’ll sit so much better. Also, look for fabrics that you like wearing. Can’t live without your jeans? Try denim shorts. Love wafting around in linen? Chances are you’ll like linen shorts too.
Don’t underestimate comfort.
said she’ll only wear loose linen shorts because they’re the comfiest. Can you sit in the garden or enjoy a long lunch in the shorts? If not, you probably won’t enjoy wearing them.Try reaching for something other than a T-shirt to pair shorts with. A tee can immediately take shorts to the camp counsellor aesthetic (shout out to
who said this) or give off tourist vibes (as lamented). Instead, go for an oversized shirt, a lightweight jumper or a loose long-sleeved top to help your look appear more “considered”.The shoes you wear make a big difference. A lot of the comments I got mentioned how shoes can make or break the outfit, as they’re much more on display when wearing shorts. I love wearing shorts with trainers or leather sandals or you could take a leaf out of Anna’s book, who said she feels much more comfortable in shorts when she wears them with loafers or ballet flats.