We Asked 5 Stylish Women: Does ‘Dressing Your Age’ Still Matter?

Cheryl Wischhover, 55, journalist, former nurse practitioner, and author of Good For Your Age Substack

I don’t consciously think about my age when I’m deciding what to wear. It’s all about lifestyle and how I’m feeling in my body at the moment, which I suppose are the indirect results of aging. I used to really love fashion, but now it’s not a priority for me, and I spend a lot less money on my wardrobe than I used to. When I find something I love, I often buy it in multiples.

I’ve definitely become trend-agnostic and adopted a uniform: button-up shirts, comfy pants, chunky shoes, the occasional blazer, simple bags, big earrings, glasses. When I first needed reading glasses, I splurged on a pair from Caddis, who have cornered the Instagram middle-aged lady marketing game. They’re something I use multiple times a day, so now I treat them like an accessory. I have a bunch of inexpensive styles I bought at Zenni Optical, and I switch them out depending on my mood. The quality is definitely not as good as Caddis, but I can try quirkier shapes.

I mostly work from home, so my philosophy is basically to find the cutest thing I can that is still totally comfortable. I have some leg and foot issues, so shoes are probably the biggest age concession I’ve had to make. No heels ever, except for dressy occasions, and then they’re low and blocky. I used to run around New York City in heels well into my 40s, and I’m probably paying for that now.

Cheryl’s essentials:

Pull-on barrel jeans
When I first saw the barrel shape emerge, I was like, nope bye. But then I tried some on and it was a revelation—they just really work for my body shape. I’ve purchased three pairs of these from Gap Factory. They have an elastic waist but still feel structured, and the price can’t be beat.