An archive sale made me think about how I dressed when I was still closeted

I thought I was just getting a sick deal, but I also got a meditation on what “timeless style” means to me

May 23, 2025

I recently made a very exciting purchase: An alpaca Doppiaa sweater from No Man Walks Alone’s archive sale that I got at a steep 70% discount. I’d been eyeing it since Fall 2022 when I first saw Ludwin Vielman and Yung Chomsky looking slick as hell in it. By the time the weather in New York cools off enough for me to start wearing it, it’ll be a full three years since it first weaseled its way into my dome, and I couldn’t be more pumped. So, today I want to evangelize purchasing and wearing something that’s technically out of style because it’s from several seasons ago.

A couple of months ago, NYT Style reporter Jacob Gallagher reached out to me and asked if I’d be interested in participating in an article he was writing about an emerging trend: Firefighter jackets. I was thrilled to participate, but I told Jacob that I was surprised to hear firefighter jackets were a trend at all.

I bought my jackets a full year and change prior to our conversation and I also haven’t seen anyone else wearing this style in the real world — boxy, cropped styles abound on Instagram, but this cousin-to-the-barn coat version feels scarce. And to be honest, I don’t see myself as someone who chases trends.

That’s not to say I’m immune to them! Purchasing pretty much anything in the present moment means I’m bringing something into my closet that’s fundamentally shaped by a specific time and place. (I love my big, billowing Monitaly pants, but I know that they could very well look incredibly outdated in a few years when the pendulum swings back toward narrower silhouettes.)

I don’t think you can extricate yourself from endless trend cycles by hopping on the “timeless style” bandwagon, though. I’ve found the most satisfaction in getting dressed when I shift my lens away from what’s current and toward what I’ve personally always been drawn to. Take the firefighter jacket: Jacob and I chatted about how it’s really just the latest iteration of the barn coat, something I’ve been rocking with in some form or another ever since I bought my first one from J.Crew when I was a teen.

There are two photos of me that clang around in my brain — one from 2014, the other from 2015. In them I’m wearing a Penfield parka jacket and a J.Crew jacket inspired by US M65 field jackets, respectively. In both instances, I’m also wearing an impossibly skinny pair of black jeans. I was deep in the closet at this point in my life but I still couldn’t fight my natural inclination toward menswear, and the tension is obvious to me: I’m dressing for myself up top, and for straight people on the bottom. (Side note: I’m not withholding the photos here because they represent a painful period in my life. I’m hiding them because the skinny jeans and heavy Valencia Instagram filters I put on top of them are tragic!!!) I was afraid of “looking gay,” so instead I just looked…like a shitty dresser? Who was also definitely still giving off gay vibes? In retrospect, an incredible self-own, and one that I know lots of closeted people inflict on themselves without even realizing it!

I look at these photos and I think about two things: 1) I’ve always been drawn to functional pieces that riff on military surplus themes, and 2) knowing who I am and being comfortable with that has made me a happier person…and so I dress better as a result!

Now that I’m in my 30s, I have the advantage of several years’ worth of data on my own personal style so I know what makes me feel like me. It’s a cliche to say that the best dressers are comfortable in their own skin, but…yes! You know when I look the shittiest? When I’m trying to emulate something that I’m being told is cool, without interrogating whether that thing meshes with my personality and taste. A trap I see millennials fall into is that they can be preoccupied with what Gen-Z thinks is cool or uncool. Millennials are young, but we’re not youths. Youths are still figuring their shit out. Sometimes they’ll nail it (M65 field jacket) and sometimes they’ll eat shit (skinny jeans so tight I ripped the crotch walking up a flight of stairs).

And besides, you know what absolutely fucking rips about shopping archive sales/end of season sales? Discounts!!!! And the knowledge that because you’ve been thinking about a particular item for a prolonged period of time, you really do love it and know it’s money well spent! “Timeless style” has its merits, but it isn’t the end-all-be-all metric for me. Instead, I’m trying to invest in what’s been going triple platinum in my closet season after season, year after year.

Making 🧵🪡

I’m this close to finishing my Joz Makes Quilts double Irish chain quilt for Valentina—my first ever sewing project. I cut, sewed, pressed, and pinned my binding strips to the quilt yesterday. All that’s left is attaching the binding, and then I’ll be done with my first quilt!
I’m trying not to get ahead of myself, but I am already planning my next quilt — this Pixel Picnic design (also by Joz Makes Quilts) for my friend Nathalie.

Wearing 👕

Kartik Research quilted shirt jacket. Definitely a splurge, but knitting has made me really appreciate just how much work goes into something handmade. I also just learned that it’s reversible as well, so…more to come on that!
Bare Knuckles basics T-shirt. It seems like the current wave of men’s T-shirts are cropped and boxy, which work really well if you’re a woman trying to achieve a straight line silhouette. I snatched this up for the summer.
3sixteen cargos (similar). I saw Andrew wearing green cargos + a brick top, so I wore cargos + a brick top.
3sixteen square toe side zip boot. I’d been coveting these boots since they were first released in January 2024, and a year-plus later I finally bought them and have worn them nonstop since.

Consuming 📚🎧📺

Overcompensating. Maybe my sappy coming out blog/walk down millennial memory lane was inspired by the fact that I just finished the first season of Benito Skinner’s new show, Overcompensating…who’s to say! It’s a satire of masculinity that makes fun of the homoerotic rituals amongst a certain type of frat dude. It also has some of the funniest line reads and sight gags I’ve encountered in recent memory (including the in-universe canned cocktail, Bitch Water).
Death Becomes Her on Broadway. Stanning Megan Hilty and demanding justice for her 13 years after Smash went off the air is probably the gayest thing I’ve ever done? If you’re in New York, you really need to see this show ASAP (and in the meantime, you can enjoy these cast recordings of “Falling Apart” and “The Plan”). More gay media made by us, for us! I highly recommend seeing this show and then watching The Substance.

Admiring 😍

Bailey Goldberg’s strawberry beanies
David Easterbrook’s wisteria bonsai that finally bloomed after 30 years (!!!)

What are your wardrobe perennials? Anything you dabbled with in the past that feels mortifyingly put-on in retrospect?