Fashion & Beauty
There was a time in my life – we’ll call it the business casual era – when I owned thirteen blazers but not a single pair of pants I actually liked. I had work blazers (essential), dinner blazers (aspirational), date blazers (optimistic), and the emergency funeral blazer (because one must always remain prepared for stylish grief, I guess). I had one blazer that only worked with a single top, and one top that only worked with a specific bra, which had to be hand-washed, which meant that outfit was basically cursed.
My closet wasn’t just a clothing repository: it was a museum of my life choices. Party dresses I rarely wore to parties, jeans too uncomfortable to sit down in (a minor detail), a pair of boots I adored even though they made me walk like a marionette, and an alarming number of clothes I’d purchased for a version of myself that had only rarely shown up to claim them. I bought clothes the way some people buy self-help books: aspirationally, and in a panic. My closet was bursting, but my daily pronouncement remained: I have nothing to wear.
It took an embarrassingly long time (and probably a few too many existential crises in front of an open wardrobe) to understand the real issue. My problem wasn’t a totally catastrophic lack of taste (though I’m sure some of you might offer a counterpoint) – the problem was that I wanted to outfit each aspect of my personality. Put simply: I was picking pieces for too many different versions of myself.
It wasn’t just that I didn’t like my options. I had built uniforms for disparate lives – I had outfits for crust punk basement shows and for summer on the Cape; for bougie branded parties and for the local DSA meeting; for ice skating competitions and for blending in at the recording studio when my boss told me to throw out any other woman’s résumé, as they likely only wanted to sleep with the band. (Being a woman is super fun, right?!)
But it wasn’t just that I was playing dress up. I was, as it turned out, costuming (and not in the fun, let’s go to a masquerade ball kind of way). No – this was the insidious, slow-creep kind of costuming where you wake up one morning, stare into the abyss of your closet, and realize that every single garment was acquired as a uniform for a specific performance – like it’s for someone else, or some version of you that isn’t the one currently staring back.
The moment that finally cracked me wasn’t a high-stakes occasion. It was a Friday night, and I was trying to find something, anything, to wear for dinner with my best friends – friends who have known me forever; who neither require, nor expect, a polished version of me. And still, I was stuck. Staring into my closet, I was confronted by a veritable sea of options, and somehow, none of them felt right for a night of shared appetizers and gossip with this group of friends. The thought struck me: I don’t know how to be myself here.
I had attire for dates, for international flights, for funerals (see: emergency blazer, above). But for pasta, or errands, or love/hate-watching And Just Like That? Nothing.
Now, let’s be clear: it wasn’t that my clothes were languishing with tags on. They weren’t monuments to my aspirational shopping. Au contraire: these pieces were operational. They weren’t just for imagined futures – they were my daily-wear costumes for a very real, very scheduled life. I had outfits for tour buses, for awkward backstage photos, for investor pitches where I tried to look like I understood spreadsheets. Outfits for dive bars (a different kind of pitch), for brand dinners (smile, nod, don’t spill), for handing over a P&L statement with a brave face.
Each look had a function, and each function came with a slightly different me that needed to be appropriately outfitted. The problem wasn’t that the clothes weren’t useful. The problem was that I had compartmentalized myself into so many different women that I could no longer find any discernible overlap. My closets were an archive of who I’d been in specific, calendared moments, but offered zero guidance for who I was when the calendar was blissfully, terrifyingly empty. (I’m sure you can guess what happened next.)
Then the world hit pause, and my meticulously curated calendar went with it. No shows, no shoots, no strategy dinners, no meetings that could have been emails. Just me, my increasingly judgmental closet, and a rotating cast of sweatpants. For a while, I convinced myself it was temporary. That at any moment, I might be called to dress for something, anything. (And at one point, I was – a Zoom wedding. I watched as their outdoor ceremony was crashed by an NYPD police boat.) But the months unspooled, and the clothes just hung there, smug and silent.
So again, I cracked. Not because the clothes were useless, but because they were suddenly, profoundly unemployed. No meetings to navigate, no flights to catch, no crowds to stand in. Just me, at home, day after day, month after month, staring down a closet meticulously built for a schedule of events that no longer existed.
I still remember when it happened: I started pulling pieces out of my closet with the manic clarity of a woman bleaching her kitchen grout at 3 AM. (Ask me how I know.) Blazers, blouses, and the chain-covered boots that had complemented my once-purple/green/blue hair – out they went. I didn’t weep. (And I certainly didn’t hold each one and thank it for its service like some organizational guru might suggest, despite my sentimental nature.) I bagged them. I moved on. The truly absurd part wasn’t the volume of what I owned, but how perfectly each item had once fit into a part of my life that no longer needed costuming.
After the Great Wardrobe Eviction, I assumed Style™ would reveal itself. That’s the promise, isn’t it? Pare things down and your True Self, fashionably clad, will emerge like Venus from the clamshell. You’ll make a Pinterest board. You’ll define your five essential adjectives. You’ll effortlessly build a capsule wardrobe in soothing shades of camel, oat, and existential despair. Supposedly, your closet becomes a temple. You become the kind of woman who wears linen jumpsuits to run errands and owns exactly three sweaters, all named.
I didn’t believe all of it, but I wanted to believe some of it.
Yet nothing arrived. No style epiphany, no sartorial lightning bolt. Just a significantly emptier wardrobe and the creeping, deeply unsettling realization that I had absolutely no clue what I actually felt comfortable in. I knew what had worked for various roles, but me, unscripted? Blank canvas. I didn’t necessarily want a capsule wardrobe, with all its implied monastic chic. I just wanted to get dressed and feel like myself. Instead, I felt like an actor waiting for a casting director to hand me a new character. I’d cut the noise, but the signal, it turned out, had packed its bags and left with the blazers. It was just…quiet. (And not the good, meditative, Gwyneth-on-a-silent-retreat way. More the bleak, is this all there is? kind of quiet.)
Eventually, I gave up on “finding a look” – which always sounds like you’re searching for a fugitive – and started looking for a standard. If I couldn’t dress for a specific context, maybe I could dress for some core values. Rules were made (because when in doubt, make rules). Natural fibers, exclusively, because a 2024 trip to pristine Antarctica had instilled in me a deep, lingering climate guilt. Fewer things, but better things – things that might actually survive more than three dates with my laundromat’s 8-load machine. No more shoes I couldn’t walk a respectable city mile in, no more patterns that were impossible to match, no more tops that were held hostage by that one specific bra.
What came next wasn’t some cinematic reveal: it was just Tuesday. No makeover montage, no triumphant strut. I just got dressed. Badly, at first. And then slightly less badly. Some days, I looked goofy. Other days I looked like myself, or at least someone I’d be friends with.
It’s a weird, slow, deeply unglamorous process, this excavation of what you wear when you’re not specifically anywhere – no event, no deliverables, no audience. Just Tuesday. Just you. It turns out, when you’ve spent a lifetime building wardrobes for very distinct, very real contexts – studios, offices, cities, farms – you can accidentally skip the fundamental step of figuring out what you throw on to buy milk. Or to go to dinner. Or, crucially, to sit alone on your own couch and feel like yourself.
There’s a very fine, often line between personal style and collective bargaining with your self-esteem. For me, it wasn’t about insecurity – not really. I think it was more about range – I was so worried about dressing to fit in that I somehow forgot to ask what I’d wear if no one else was there. I think that if you really want to know who someone is, don’t look at what they wear – ask what they keep and never don, just in case. I kept a lot. I did wear almost all of it, at some point. But when I was finally alone, I realized I didn’t know what any of it meant. Not about the world, but about me.
These days, when I get dressed, the outfit isn’t the answer. It’s the question. And at least now, I have a much better idea of who I’m asking.
How To Start
So, your closet? Does it feel less like a curated collection and more like a holding pen for a witness protection program of various past selves? Are you staring at a bewildering array of “stuff” and thinking, Surely, one of these things must feel like…me? And have you, like me, Googled for help only to be met with blindingly obvious advice that makes you want to scream into the nearest sensible scarf? (Wow: Buy what makes you feel good? Oh man! Insightful! What wise chestnut is next? Avoid hitting yourself on the head with a hammer?)
I’ve been there. It sucks. Here’s what I’ve found helpful when it comes to clearing the clutter and making room for Style™, whenever it decides to show up (any day now, I’d hope).
Pare Down
Donate: I donate my basics to Goodwill. You can also keep an eye out for those in your community who are in direct need of aid – Jess and I pooled our donations and were able to outfit a Pasadena teacher who’d lost everything in the Eaton Fire. (Shoutout to Sara Tramp for organizing!)
Trade: Got stuff that’s seen better days? (Like, way better days?) Anything stained, ripped, or hole-y? Don’t throw it in the trash – I swear by Suay’s $20 textile bags, whose cost can be reapplied to any Suay product. (I love this business. Like, they’ll deal with all my icky textile crap, and I can get a stellar lumbar pillow out of the deal?)
Sell: Okay, I admit I clung to some of my “splurgier” uniforms – I mean, pieces. Wedding guest dresses I swore I’d wear again (I didn’t), trousers that promised a new, leaner me (they lied), matching sets that looked great on the hanger (the betrayal!!!). I’ve had a ton of luck offloading these pieces on Poshmark, though! I initially balked at the time commitment, but then I made $200 back on a dress I’d only worn once. It was an incredible return for 5 minutes of my time. (There are alternatives here, but this is the only one I’ve vetted.)
Consign: If the thought of photographing another blouse makes you want to lie down, look for local consignment shops. (If you’re in LA, The Left Bank is a solid bet.) Just let someone else do the work and collect a (smaller) check. Worth it. (If you’re a size 12 or above, your clothes are always in demand at consignment stores, FYI.)
Index (Or Indyx)
As it turns out, I suffer from a peculiar affliction: I cannot, for the life of me, conjure images in my mind. When people talk about their “mind’s eye” or “imagining the audience in their underwear” – well, I always thought that was a literary device. Metaphorical. Implied, not literal. A charming turn of phrase! It was only recently I learned that most people can, quite literally, see things in their heads. (Given a natural inclination towards distraction, perhaps this is a mercy. I would likely spend my days conjuring pastries.)
But this posed a silent, daily problem for my wardrobe. I knew the facts: I owned black linen pants. There were tank tops, somewhere, in that drawer. My favorite dress was red, with zodiac signs. But I couldn’t see them. Couldn’t picture combinations. Getting dressed was a daily archaeological dig involving pulling everything out and sighing dramatically.
Enter: Indyx. (Link Up readers, you may be familiar.) Cataloging my clothes felt absurd at first, but it was – and I’m not being overdramatic – transformative. I can actually scroll through my clothes like an ultra-specific personal shopping app. I can play mix-and-match before creating Mount Laundry on my floor. I can see what I actually wear (and, more importantly, what I consistently ignore). It’s a process, not a miracle cure. You could do the same thing with a photo album on your phone, but Indyx is prettier.
Live Out of A Carry-On
This one has been the most helpful, I think. I’ve spent 4 of the last 5 months living out of a carry-on suitcase. I’m not even suggesting that you have to travel to do this – you could also try it at home! – but there’s something liberating about pulling only what fits in a carry-on suitcase and learning how to mix-and-match from a refined, edited collection of only essentials.
Suddenly, faced with a severely limited selection, I was forced to actually style things. That button-up? Can I tie it? Can I tuck it differently? That dress? Can it be a skirt? Can it be layered? It stripped away the paralysis of too many options and forced creativity. It also gave me a clear metric for success: when I felt genuinely bummed out that something was in the laundry hamper because I wanted to wear it again, I knew I’d found a winner. These were the pieces that felt like me, even in miniature form.
And Rent, For Some Variety
PRAISE BE TO THE NUULY FOUNDERS. I’m still on the hunt for my Style™ – it feels like a mythical creature, sometimes – and opening my subscription is my low-stakes safari. Six pieces a month means I can try cuts, colors, and general aesthetics I wouldn’t commit to buying (or, honestly, even trying on in person). It’s a lifesaver during the brutal LA “winter” (read: jacket season) and the holiday party circuit (no more staring mournfully at unworn sequin dresses!). It’s experimentation without the commitment – perfect for this phase of life, while i figure out who I am. (I guess I’m just starting that mid-life crisis a few years early, huh?)
What say you? Any thoughts? Tips? Advice? I can’t be the only woman whose path to self-discovery involved staring blankly into a closet, can I? Has this happened to you? CAN WE TALK ABOUT IT?
Read More
