I grew up attending Catholic schools. Blue plaid jumper, white blouse, navy knee socks. Every day, the same. High school brought a green plaid skirt and an itchy vest. The point was to remove the question entirely. What you wore wasn’t an expression of anything. It was just the answer to a problem.
I spent a long time carrying that logic into adulthood without realizing it.
Not literally, ( thank goodness), but the underlying idea stuck. Find the thing that works. Repeat it. Remove the friction. Steve Jobs had his black turtleneck. My version shifted depending on the season of life: work Trish, school-pickup Trish, the rare date-night Trish when the kids were little. I even had a uniform for the years of sidelines and bleachers - every weekend, every sport, every weather condition. I look back at pictures of myself and I can almost chart my life by the rotating costumes. Each one practical. Each one efficient. Each one entirely beside the point of what I actually wanted to wear.
Capsule wardrobes. Ten items, infinite outfits. The whole enterprise of simplifying the question of yourself down to a formula you can execute on autopilot.
I understand the appeal. I do. But I’ve realized I want something different.
I don’t want a uniform. I want to wear how I feel that day. Some days that’s put-together and intentional. Some days it’s soft and a little undone. I want the outside to have something to do with the inside, which means it has to change.
I’m not all the way there yet. I’m still figuring it out. But lately I’ve been having more fun with it than I’ve had in years, and I think I know why.
I stopped looking at Instagram for instructions.
Not entirely. I’m not immune, but I noticed I was buying things because an influencer made them look like the answer, and then feeling vaguely off when I put them on, because they were her answer, not mine. Her bone structure, her life, her vibe. I kept trying to import a style that didn’t belong to me and wondering why it didn’t quite land.
So I started going the other direction. Vintage. Specific. Things with a history I can only partially know.
My current favorite piece is a cardigan I found at Stickball. Old varsity style, school initial A, number 72 ( graduation year?), and on the sleeve, in worn letters: Dorinda. I have no idea who Dorinda is. I have no idea what she was like, where she wore it to, whether she loved it or shoved it in a bag without a second thought. The sweater isn’t telling.
But I think about her when I wear it. I like that it came from somewhere. I like that it has a story I’ll never fully know. I like that when I put it on over something simple, it looks like exactly nothing you’d find on anyone’s Instagram feed, because it’s a one-of-one that belonged to a real person first.
That’s what I’m chasing now. Not a uniform. Not someone else’s aesthetic. Just things that feel like mine, or things that were someone else’s and are mine now.
I’m 55 and I’m still figuring out how I want to look. That used to feel like a problem. Lately it feels like the most fun I’ve had getting dressed in years.
Dorinda, wherever you are, thank you for the cardigan.
I write about this kind of thing in Bloom. — a newsletter for women in their 50s who are paying attention to this chapter.
