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Life Lessons

What Does Dressing My Age Look Like?

10:28 AM EST on November 22, 2023

NEW YORK, NEW YORK - FEBRUARY 13: Brad Pitt is seen on the set of "Wolves" in Old Howard Beach on February 13, 2023 in New York City.
James Devaney/GC Images

I don’t know how much longer I can look like this. It’s fall in Canada. I run cold. So, I am wearing a black hoodie, an army-green toque (a “beanie” to Americans), jeans, and a T-shirt. Not a band T-shirt, but a T-shirt with Winona Ryder on it (it’s a present from my brother—Ryder in that scene at the end of Beetlejuice where she’s floating in the air in her school uniform). Maybe that’s worse than a band T. Or maybe it’s worse that I also have chipped black nail polish on (a two-week-old manicure). I’m not wearing Converse at least. I actually would, but I’m so old they don’t provide enough arch support. I have to wear overly expensive Danish shoes instead or my feet hurt (I suffer from something called over-pronation). They look like sneakers but not really. They look like septuagenarian sneakers. Like sneakers Larry David would wear. Larry David is 76. I am 43. I am actually closer to the age I was when I first started dressing like this than I am to his age. But only barely. Which is perhaps why it is now starting to feel weird. Like, when am I supposed to stop looking like this?

My brother likes to say I dress like Brad Pitt. I don’t dress like Brad Pitt. He means I dress like a certain ilk of middle-aged American actor. The kind of middle-aged American actor that still seems arrested at around 23. Ethan Hawke is one. Unfortunately, Johnny Depp is another. You see them in paparazzi photos wearing slouchy black beanies, plaid shirts, and distressed jeans that cost more than five months’ rent. They look grizzled and permissible in that way that only men can be permissible. Like he’s-dressing-too-young-and-his-girlfriend-is-too-young-but-he’s-an-artist-so-it’s-OK. You see actresses dressing this way into their 30s, maybe, but as they get older, they start transitioning. They start looking more like Patti Smith—black blazers, black boots. Chic. Women are always expected to be more put together than men because men always get the benefit of the doubt. And in hoodies and sneakers lies doubt.

Just for kicks, I looked up how I am supposed to be dressing as a woman in my 40s, according to … websites. Just as I thought: a lot of blazers and long dresses and skirts. According to the Today Show (lol) it’s about quality over quantity (code for: you are supposed to be better off by this point, so stop looking like an undergrad) and flattering textiles (code for: you are probably fatter now, so stop wearing Lycra). Speaking of flattering, I know the Queer Eye guys talk about what’s attractive on men, but let’s be real, men do not generally have the kinds of curves that women have, the kind that can make your shirt gape at the chest and your jeans gape at the ass. They don’t tend to put on weight in the same way (in the upper arms and in the hips). Clothing tends to be sold on straight-lined models and mannequins, and men, just physiologically, often fit the silhouette better than women. Perhaps this is in part why you find the same men at 43 and 23 wearing the same style unapologetically. Meanwhile, as women get older, as their boobs and butts drop, as their curves start to lose that hourglass quality, they are encouraged (because of sexism) to make up for it with various tricks. Tailoring matters, and so does flow, which would seem contradictory, but I get it—I have oversized linen jackets, but they fit me, if that makes sense. The other thing that comes with age, perhaps to make up for the shapelessness, is alarmingly colored fabrics. I don’t fuck with that.

It’s kind of late to be questioning how I dress, maybe, considering “adulthood” happens way before 43. But if you think about it, once you’re into your 40s, all those things that traditionally, conservatively, socially make you a woman—kids, a husband, a house—if you don’t have them, you might question your identity as a mature one. (I imagine men feel less compelled to do this, just going by the fairly well-established permission they seem to have to act like toddlers well into their dotage). I have always leaned on work for value (I know, I don’t want to hear it), but at this stage, it’s painfully obvious that the kind of work I do, particularly as a woman, cannot compete. So then you start noticing other markers that might be keeping you subpar. Like your clothes. And then you start looking at other women your age and how they dress—around me, a lot of Blundstones and black leggings and cashmere (stroller optional)—and you strike that, but then you look at people you respect, like maybe your family, like when they were your age, and that’s a whole other confirmation that you're not doing it right. 

No one in my family dresses like me. My brother, who is older, always had this idea—I think it was based on a writer he loved—that grown ups should wear suits. Or something along those lines. If he wears jeans at all they tend to be dark. He wears cardigans and sweaters. He wears buttoned shirts. He teaches at a university so this makes sense. It also fits into my brother’s historic position as the mature one. It makes sense that he’s an adult, it makes less sense that I am. And how he wears that adulthood makes sense considering how our parents did. Both of them were doctors so they predominantly wore suits. I barely remember what they wore on weekends, but they did not dress like me. I think not remembering is the point. I probably would have remembered if my mom and dad wore band T's and jeans with holes in them and toques. But I don’t remember anyone’s parents dressing like this when I was a kid. Of course, I see parents dressing like this now. OK, I see fathers dressing like this.  

It just hit me that one of the reasons I am thinking about this now is not just my age, it’s the sudden feeling of relentlessness. If I am an adult, I should be making my own rules. But, no. The rules are the same as they ever were, they just have better tailoring.

When my mom was my age, as it was just turning over into the ‘90s, streetwear was something that was JUST starting to hit the mainstream, having emerged from New York hip-hop culture, and earlier punk and new wave (with some Japanese trends no doubt instrumental—the provenance of fashion waves is always a little confusing and I’m not a style historian). By the time I was a teenager in the mid-90s, skateboarding and rap (or, in my case, grunge) brought with them merch, just in time for teenagers like me, who were forming their style, to dress like the bands we loved. Bands that were mostly made of dudes. That’s when I started wearing shoegaze shit—the toques, the plaid shirts, the ripped jeans, the Converse, the hoodies (quick side note: I had no idea Champion invented hoodies almost a century ago to protect athletes and laborers, but we love you for it, Champion). Remember, this was in the mid-90s, when I was supposed to be wearing baby tees and barrettes. I imagine many of the male indie musicians I was listening to then are dressing the same way as me now. Try to imagine a 43-year-old woman in a baby tee and plastic barrettes.

There was a brief period when my mother was not complaining about my clothing. It was pretty much the decade from my early 20s until my early 30s when I worked in newsrooms and other offices. Obviously, I had to look more presentable in a workplace, which involved, you know, slacks, skirts, blouses, blazers, and cashmere sweaters. No jeans. No hoodies. No beanies. No Converse. I had longer hair then, too. It’s harder to get an office job with a shaved head. If you’re a woman. I imagine.

But then I started freelancing and it all went to shit. I’m kidding, sort of. But it’s true that I could wear whatever I wanted to (I think this has increasingly been happening to many of us post-pandemic, with the lackadaisical return to the office and half of us working from home half the time). That meant all of the stuff I am wearing right now, with a brief dip into higher-end sweatpants (my mom insisted on sending me some) during the pandemic. That’s the other thing, because streetwear eventually invaded luxury couture through sports brands, now it’s possible to upgrade your hoodie and toque and jeans to at least a ritzy version which can pass as, I don’t know, loungewear. That’s also where the collapse in age becomes OK—that is, you can wear streetwear as you get older, as long as it’s made of natural fabrics that few can afford; which is to say, as long as it’s gentrified. I can imagine all those dads I see in my area that are dressing like me, with their engineering jobs and the houses they own with the generous help of their rich parents, are probably wearing way better quality apparel than I am. But from far away, in this upper middle class milieu, we’re virtually indistinguishable.

So, sure, maybe if I had all the money in the world, I would fit in better with the adult women around me. But, I don’t know, there’s something about getting lost not just in comfort but in the past, about not dressing to my body, to my gender, to my age, that feels like a little daily protest. Maybe it’s a childish protest, but that’s fitting, right? And, in fact, there seems to be one inclusive motto at least that has leaked from the godforsaken self-help arena into fashion (or maybe it’s from the more inclusive youngs rising up in the tastemaker ranks): wear what works for you. “There isn’t an age cut-off for streetwear,” stylist and photographer Chris Tang says in the delightfully named Fashion Beans, one of the rare places I found a fashion expert talking about this age thing. “But an older guy should stick to what they like and what works for them.” So, cool, thanks, Chris Tang, this guy is sticking to hoodies and toques. Even if she’s not a guy. Sorry, mom, and I guess also sorry to whatever dad still seems to be running society at large.

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