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A recent Thursday found me and a male friend huddled over his iPhone. It was 11 a.m. sharp, and the men’s skate-clothing label Supreme was having its weekly drop of new merchandise. My friend, a Supreme fan, has admitted in the past that he goes into something of a fugue state during its weekly online drop, clicking near blindly to secure himself something, anything, before it’s gone. This time, I was a fellow traveler.

Established in 1994 in New York, Supreme has developed a cult following among not just skaters but also fashion folk, artists, musicians and streetwear-obsessed suburban teenagers. Known for its limited inventory, its clothing’s high resale value and its many collaborations with other brands, Supreme releases its merchandise on Thursday mornings in stores and online. Many of the items — most of them staples like hoodies, caps and T-shirts — sell out almost immediately, creating an enticing scarcity.

My experience was no different. As I scrolled through the Supreme app with my friend, I found that things were moving too fast for me. Before I could decide whether I wanted something or not, it was sold out. Dark blue Supreme x Clarks wallabees? Gone. A Betty Boop baseball shirt? Gone. A red polka-dot short-sleeve button-down? Gone. I felt slightly embarrassed. This might not have been the thing for me, but nevertheless, here I was: a 40-year-old cisgender straight wife and mom who shopped like a 19-year-old skater.

A LOT OF girls are tomboys, and growing up I definitely was one, but what began in my childhood as a relatively unconscious, oppositional response, a sort of sensitivity of the body — the lacy collar on that dress was itchy; the strap on those patent leather Mary Janes gave me blisters — developed over the years into a more intentional style inclination.

At 12, I went to see “Married to the Mob” and decided I wanted a haircut like Matthew Modine’s. It’s not that I didn’t think Michelle Pfeiffer’s perm in the movie looked amazing (she played a hairdresser, after all), but Mr. Modine’s preppy, 1920s-style cut seemed to me exponentially more appealing. Unlike Ms. Pfeiffer’s femme resplendence, which looked even to my novice tween eyes like a ton of work with plenty of room for error, Mr. Modine’s boyishness appeared effortless, and therefore cool. It was, at least seemingly, low stakes, and by virtue of that very carelessness became a look in itself.

As I discovered once I got the haircut, it took some effort to maintain, with my wavy hair erupting into a mushroom cloud instead of the hoped-for straight, vaguely New Wave-ish cap. But while this apparent failure might have deterred me, it actually became a spur.

The thing was, I didn’t particularly want to be a boy, and I wasn’t trying to approximate any look fully or exactly; what I did want was to look like a girl who was obviously lifting particular boyish elements and incorporating them into her style. That way, fashion could be free to become purely a signifier, a concept, and the more pared-down, simple and iconic the better. Fashion that so clearly and self-consciously borrows its language could never be accused of failing, of getting something wrong — as I would surely be, I thought, if I tried to look more overtly feminine.

Over the years, I plucked many such signifiers from the world of casual, lightly subversive men’s wear and planted them in my outfits. It was crucial that none of these items be dandyish or precious or conservative. I would have never worn a suit or tie, for instance. Instead: a fuzzy oversize Steven Alan cardigan that put me in mind of Kurt Cobain’s “Unplugged” vintage sweater; a thin gold chain, worn with a plain T-shirt and hitting midsternum, reminiscent to me of that worn by Fassbinder’s young hustler character in 1975’s “Fox and His Friends”; a Rodarte sweatshirt I bought at a sample sale after I saw a paparazzi picture of Drake wearing it at a club; clear-framed, oversize glasses of the sort Marc Jacobs used to wear in his slobby-hot days in the mid-2000s; and so on.

As I’ve grown older, had a child, advanced professionally, the gap between the clothes my stage in life called for (Theory? The more tailored section of J. Crew? Ann Taylor Loft?) and what I actually wore (slip-on Vans) became ever wider. This pleased me, to an extent. It was like an inside joke that, admittedly, maybe only I enjoyed. But I also wondered, in my more self-questioning moments, how much older I would have to get before it became fully weird for me to keep adopting fashion elements more appropriate to a teenager.

Recently, there has been some talk about so-called Coachella moms, women in their 30s and 40s who, in anticipation of attending the Indio, Calif., millennial-magnet music festival, invest thousands in skimpy designer clothing — not to mention in surgical and dermatologic procedures — to remain youthful-seeming and sexually viable for as long as possible. More power to these women, I thought, as I read a hand-wringing article written about the phenomenon. But although I was a mom, too, and just beginning my 40s, the effort to become a more vigorously gendered version of myself wasn’t, again, what interested me.

TRAINING MY SIGHTS on Supreme as the next step in my men’s wear journey seemed a strong, and somewhat improbable, commitment to make — which also struck me, immediately, as a win for the comical. Wouldn’t it be funny if I chose this moment to brawl with teenagers for a Supreme hoodie?

The hilarity was, however, undercut by some seriousness, a joke but not. In David Shapiro’s very good coming novel, “Supremacist,” the protagonist travels from New York to Los Angeles to London to Japan and back to New York again to visit every Supreme store in the world. And while I wasn’t intending to be anywhere near as fanatical, I felt as if I could still understand this pilgrimage’s arc, with Supreme as the conceptual McGuffin standing in for what one wants but can’t fully have: a coolness, an offhandedness, an ease with the body — in sum, the imagined perfection of the symbolic phallus.

AFTER THE DUST of the Thursday drop settled, I checked the Supreme app again. A leopard-print sweater vest had remained available, which seemed lucky and somehow civilized. I didn’t have to battle like a wild dog for scraps, after all. I didn’t have to try that hard, thank God.

I ordered the vest.

It happened to arrive the day before my daughter’s fifth birthday, and I decided to wear it to the party. This seemed like the potential crossing of a limit — wearing Supreme to my child’s preschool event — but while I felt a little awkward handing out cupcakes and tying balloons to tree trunks in streetwear separates, people didn’t seemed to notice or care. And why would they? If it hadn’t been clear enough already, it was now: This was between me and me.

And so, after the party, my daughter having gone to bed, I stood in front of the mirror: Who did I remind myself of? Was it Fassbinder, but this time the older, fatter leopard-print-wearing Fassbinder of “Kamikaze ’89”? Or, after tucking the vest inside my pants, was there a hint of Young Thug mixed with Cary Grant in weekend wear in “To Catch a Thief”? And while I knew these visions were largely delusional, and realized fully what else I saw — a 40-year-old mom wearing a somewhat ill-fitting patterned vest — it didn’t matter. At that moment, I felt as if I were smoking a cigarette without having to actually smoke a cigarette: unfussy, nicely sloppy, trying by not trying.