getting dressed 03: Lily

"You don’t need to and in fact shouldn’t look sexy while you workout" and other gems

getting dressed is a series featuring the people I love and the ways they interact with fashion and clothing in their daily lives. You can find the previous installments here and here.

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I met Lily on Tumblr in 2009 or 2010, and we met IRL for the first time at a bar in Williamsburg in 2011. She catalyzed another era of living in New York for me, and I like to think I did the same for her. Navigating the turmoil of your early twenties is never easy, but with Lily, I never had to do it alone. We lived together for a time and I can confidently say you have never seen a better book collection than our combined bookshelf. Lily has long been one of my favorite writers, and I think after reading her interview she will become one of your favorite writers as well. (She has also become one of my favorite artists after taking up painting during early Covid, and I am honored to have several pieces of her artwork displayed in my apartment!)

in front of our collection in our apartment in 2013 (?)

This interview was conducted over email and text message.

Lily wearing a dress that both of us would consider a ‘Maria’ dress (from TSOM)

How does your life (job, where you live, what you do on the daily, etc.) shape your wardrobe?

Oh my god THANK YOU for asking this because whenever I move (which as you know is horrifically frequently) I’m like “why do I have so many clothes??” And it’s because I have so many lives.

• First, I work from home, so I need bottoms that are comfy enough for couch typing but presentable enough for Williamsburg coffee runs (truly a purposefully schlumpy fashion gauntlet).

• Then, I’m a runner and running coach, so I have a solid amount of running clothes, including a couple things I’ve literally had since high school, summer version and winter version.

• Then, I have my, like, actual life where I leave the house and wear cute clothes.

• And then, my body and style have changed a lot recently (more below), so there’s second Actual Life clothes.

• Then there’s a few pieces of professional clothing for the approximately 5x a year I actually do have to leave the house dressed like a grownup.

• Then there’s the actually comfy not-so-presentable clothes for sleeping and lounging.

• And then, I paint and I’m a very messy painter so half of the comfy clothes are paint-designated but that number is ever growing when each time I go to paint I think “enh, this can get stained too fuck it.”

a longline sports bra and pearls! who else!

Has has your style changed from when we first met in 2011?

Oh god honestly it’s changed MULTIPLE times. With, I suppose, a throughline of — I guess I would define it as a cinematic vision. Not cinematic in an exciting way, but in a way where I imagine the montage portion of the movie or TV show, the shot of our heroine riding the bus, going to work, getting coffee. I suffer from seeing my life as a television scene, but that’s a question for a different newsletter.

What’s changed. First of all, and I’ve said this before, but the worst thing that ever happened to me was learning to be able to tell when things are expensive. So I am MUCH more particular about fabrics and construction. Literally sometimes bad polyesters make me physically ill. And that sounds snobby and perhaps it is but there’s a third very different newsletter we could do about the actual damage that polyesters, their creation, and their disposal do to predominantly poor people and people who live in the Global South. But whatever I wear silk and cotton and linen.

Stylewise, we met when I was 21 (wild) and I was in the first blush of “I don’t see that I’m pretty but men sure are responding to me like I am!” So I didn’t have a lot of confidence but I was dressing in a way where I was very much discovering and negotiating how the world, and especially men 6-10 years older than me, would respond to me. Sluttier, for lack of a more concise term.

Lily in the era when we first met

I then went through what I would call, so far, my sweet spot, age 28-29. Was hot and knew it, dressed in ways that made me feel beautiful and interesting, but were about how I felt more than what I thought would be maximally hot to other people. Had this really great curly bangs haircut that I thought (correctly) made all my outfits look better and more interesting.

And when I moved to DC in 2021, I went through a kind of fun phase where I didn’t know a ton of people or have a ton of a life outside of work, so a big part of my daily joy came from putting together Silly Little Outfits of vintage clothes that were technically professionally appropriate clothes for fundraisers and stuff, but that didn’t look just like everyone else who was getting off the Metro at Capitol Hill South every morning.

Silly Little Outfits era!

And now I am in a phase, I fear, where the shape and size of my body have changed, as has my sort of age group and self-perception as an adult, and I’m having trouble knowing what I want to achieve with my clothes or how to achieve it and often what I long for is something truly neutral. Not, like, beige, but like an outfit that would say NOTHING about me and function simply as a way to cover my body acceptably. But of course I’m a person in a context, and most especially a woman so that doesn’t exist, in the same way that if I don’t wear makeup it’s a statement as much as if I wear blue eyeshadow.

Where do you get your clothes?

Almost always secondhand, which is partly an ethical thing and partly the quality of garment I want I can’t afford new. For a long time it was instagram vintage accounts — that’s where I got all my fun Quirky DC Professional clothes. I still follow those accounts (and can rec a few if you’re interested) but buy less since my budget has adjusted and also I’ve been having less fun getting dressed. I’ve also moved away from Thredup because it is SUCH a gamble — when they put measurements on those clothes I swear to god they just pull them out of a bingo ball spinner like these numbers are worse than meaningless why even put a number just say you don’t know how big the waist is!! Can you tell I’ve been burned? [Eleanor: the RealReal does this, too! WHY?] But it’s still good for if you’re literally like I need some clothes to cover my body to go to a business casual job, let me buy like seven secondhand Gap pants for $8 each and probably at least two will fit.

So where do I get my clothes. The answer is mostly I haven’t been acquiring them. When I do, it’s hand-me-downs from friends because that doesn’t require a decision or nuuly because I subscribed a while back to rent a gown for an event and I canNOT get the clothes back in time to cancel each month so whoops I gotta rent some new silly clothes. I do think it’s slowly helping me regain my sense of fun in dressing.

Lily in a rented dress from nuuly

For comfy clothes, there is simply no better source than hand-me-downs slash borrowed/stolen clothes from friends and lovers (sorry) and since I haven’t had many sleepovers of either kind recently these are kind of dwindling :(((( ty to the guy I dated who worked for a running company and played soccer your castoffs are really carrying more than their weight years later.

For workout clothes — ok this is another sore subject. IN MY DAY (2009) you could just GO RUNNING and no one would take your picture. And now everyone is wearing matching sets and every run must be memorialized for the gram and the West Side Highway is famously the horniest place in New York City. All of which to say, most of my workout clothes are at least five years old and all of them of every age are from Old Navy which are perfectly comfortable and last a shocking amount of time but don’t look Hot while you run. I’m all for spending more if you can and IF the brand is ethically produced but literally I can’t even find a brand that says it treats its workers well so at that point just buy some ugly Target shorts that will last, threadbare, on your adult human butt as you move through 5k age groups inexorably towards death. You don’t need to and in fact shouldn’t look sexy while you workout this is my hot take.

What garments/outfit/outfits make you feel most like yourself?

Always and forever a high waisted wide legged trouser with a cropped top is going to be my ideal. Last year I found out like 3 days in advance that I was going to an event at the White House and I used it as an excuse to do my rare in person new-clothes shopping and ended up with some black trousers and a cropped boxy white buttondown which I wore with a vintage cardigan clip on the lapels and an absolutely disgusting pair of Nine West heels I’ve had for job interviews since 2015 and my favorite discontinued red lipstick and I looked exactly how I wanted to look, actually, for once.

I also have an XL men’s Tommy Hilfiger red and white striped button down that I bought for a Risky Business Halloween costume in 2015 and now throw on, barely buttoned over a bralette, every other day to run errands or go for quick drinks and it made the cut for this two week trip to Europe. It’s never the clothing you expect that becomes your uniform!

Do you have a favorite secondhand clothing find or story?

So that red dress that you lent and then gave to me [Eleanor: I FORGOT ABOUT THIS DRESS. WHAT A DRESS.] I’ve talked about this before but for those who weren’t following me on Tumblr in 2013 — Eleanor had this red mini dress from the best secondhand store in Tampa. It was just short enough without being Too Much (or it was when you were 22 and weighed like three pounds) and it had a little boob cut out that, again, was subtle for a girl in her early 20s ho phase, and was made of this nice material and had a good zipper — not one of those cheap ones that you think is gonna break your hand to zip up even when the dress fits.

And I had just ended things with The Situationship. We all have many throughout our lives but this was THE one that makes you think “how can I feel so much about someone I’m not even dating???” The one that would linger for many years, who was handsome and charismatic and who I worked with (of course). I was just an absolute little fool because he was so smart and funny and sometimes, like once a month, I could say something that would make him look at me like I too was smart and funny and he was pleasantly surprised to find it out and maybe this would be the smart and funny thing that made him care about me. You know, you’ve been 22 (and 23. And 24. Don’t worry about it.)

So anyways, I was going to some kind of coworker going away thing and the ending of the situationship was new and he was going to be there and I was feeling fragile without feeling allowed to be fragile and also WHAT WAS I GOING TO WEAR. And there was Eleanor, with this perfect little red dress that made my boobs look good and my waist look good and like I wasn’t even trying THAT hard and it was imbued with her spirit and that of her old roommate, Natalie, who’d also borrowed it once, and between the three of us and that dress I could make it through and I wore it with the incredibly slutty red lipstick/gloss combo I wore at that time that made my mouth look like a tootsie pop and I had an ok and mostly dignified time. And I still have that dress.

Also once I came up to New York from DC for a friend’s Black Tie wedding and I had a dress that I hated but would work. On an impulse that morning I stopped at the Housing Works on the UWS and found a used silk Anthropologie dress for $25 that fit me perfectly in the style that I prefer.

Do you have any fashion or style inspirations? Who or what are they?

Ok so the style I prefer — 30s and 40s vibes. Not costumey, but the silhouettes/cuts. In that vein — Katharine Hepburn forever. I also LOVE Eartha Kitt’s entire vibe and style. And Debbie Harry. But mostly it’s my friends and coworkers and the girlies on the street in Williamsburg. Also 90s romcoms, specifically While You Were Sleeping (giant sweaters, actually ugly and warm clothes), and When Harry Met Sally. Sally’s clothes, obviously, but I mean this precisely and literally: I would wear every outfit that every single character in this film wears (Harry’s sweats at the batting cages, 80s New Year’s Eve party dresses, the puff sleeve wedding dress, Helen’s giant shoulder pad suit, EV.ER.Y.THING.) Except two items of clothing: Sally’s khaki Bermuda shorts in the apple pie a la mode scene, and Jess’s horrible jorts in the wagon wheel coffee table scene.

Lily re: censoring this child’s face: “I hate it aesthetically, but morally it’s correct”

I’m also obsessed with an obscenely low back. Like, puritan in the front, Madonna in the back. Just above the butt crack. Bare the whole back. Love it.

Are there any items or styles of clothing you’d want to wear but feel like you couldn’t pull off, or it feels too different from your normal style?

I mostly think I can pull off anything if I like it, in the sense of outrageousness or whatever. I used to think I “couldn’t pull off” strapless because I’m so flat chested but then I decided I liked it. I think some people still think I shouldn’t wear it, but that’s none of my business because I like to wear a strapless top.

So it’s not “can’t pull off” in the sense of what other people think. I’m still struggling, though, with outfits that don’t match the image in my head. Like I’m imagining them with like coltish skinny legs to make them work — probably mainly a mini skirt with big giant boots. I could “pull that off” in the sense that it would look fine or even hot and no one would say anything, but it wouldn’t look the way I imagined it, I wouldn’t match the television scene in my head.

What’s the most recent item of clothing you purchased?

In Paris (lol sorry) I stopped at a secondhand store and found a black blouse that turned out to be a lovely silk/cotton blend for 5 euro, and in another store I bought a new sweater for 35 euro because I’d been looking for a black stretchy one and this one was good and also the middle aged French woman who owned the store told me I looked like a movie star and she liked my pants, before she even realized I was American.

What is your holy grail or “white whale” item, if you have one?

This isn’t like lifelong but for the past couple years I have really wanted a good black miniskirt. It needs to be high waisted, fall right even though I have an ass, hit ALMOST scandalously short but not so short that sitting down is a gynecological event, and maybe have a little slit. I adore this one that I rented on an impulse but I fear it’s not basic enough/too silly and if I buy it I’ll one day become less enchanted. Slash I can’t picture being 45 and wanting to wear it. And with it, I’m always looking for the perfect pair of secondhand knee-high black boots with a low heel and a pointed toe.

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Thanks, Lily! You can find more of Lily’s writing here and her painting here.

one of Lily’s paintings that hangs on my living room wall