Here she is: my inner child. The one who loves dressing funky even at 2 years old. Observe my little hand gesture: so fancy. The honest truth is I’ve always loved expressing myself through an outfit. No surprise — I’m a Halloween child, whose birthday was always celebrated in some kind of costume. But the past 20 years I’ve been out of touch with that inner child: focussed on raising my kids and running my business, my outfits were mostly whatever I would find dumped on the bedroom chair from the day before — and increasingly the choices are few as I’ve definitely changed shape in the past two decades of child bearing, menopause and all those other challenges that mean an end to wearing a favorite dress or pair of jeans that I bought maybe 40 years ago.
Regardless, for decades I’ve been toting around a lifetime accumulation of clothing — from country to country, and coast to coast; my own clothes, selected over the years from vintage shops and sales across continents — and a fair amount of hand-me-downs from my well-dressed grandmothers on both sides, my diminutive grandfather, my chic mother, whom many of you saw in one of her unforgettable outfits, in this post.
The wardrobe bulges with clothes that no longer fit me, like a time capsule of my itinerant life. There’s the LBD I bought vintage back in the 80’s, the Portuguese avant-garde dresses from when I worked as a screenwriter in Lisbon in the early 90’s, High Street frocks from my years pushing the baby carriage along the seafront in Brighton, a fabulous zebra-striped full length gown with a feathered bolero, that I bought on sale at Dolce & Gabbana in London for my wedding dress.
And then, after the Woolsey Fire (when I evacuated with only an overnight bag and the fire then ripped through our canyon), a full capsule wardrobe of clothes was generously donated to me by one of my home delivery customers who had a fashion showroom in DTLA, to tide me over for about two years before my own clothes were returned from Fire Remediation, cleaned and pressed — perfect apart from a series of matching belts which went missing. As anti-consumerist as I am, fundamentally, the only clothing I bought for myself during the 20 years I lived in LA was a selection of loose linen dresses and tops from the lovely Rachel Craven, another of my LA home delivery customers, who made beautiful clothes that I would snatch up whenever they went on sale (now she’s making pottery!) Moreso, I focused on buying beautiful vegetables, in all shapes and colors — the retail therapy part of my job not entirely lost on me.
But about two weeks ago, I came to a moment of reckoning. In my new day-to-day life in Maine, apart from jeans and mud boots for going outside, I schlep around the house in ridiculously oversize fleece long underwear left in the house by the late Andrew Palmer — an English expert on ocean pipelines, and visiting professor at Harvard. Fuzzy and warm, indeed, but about 9 sizes too big.
When we moved in to the farmhouse, not only did we inherit all the kitchen items, but also closets bursting with clothes and linens (and incredible antique patchwork quilts, embroidered napkins and hankies), all left here by Andrew and Jane Palmer. Adding their clothes to mine only exacerbated the wardrobe situation. At first, I was quite charmed by Jane’s Marks & Sparks jolly practical English basics, the decades-old LL Bean arctic winter coats and flannels, the military parka, English overcoat, and the work jacket for the garden — and even Jane’s galoshes. You can read, in Becoming Jane, about my experience when we first moved in and I adopted some of her clothes for painting and gardening... Since we moved in, sorting through the clothes has seemed a Herculean task that I was overwhelmed by.
So now, two years in, the ground floor of the house is mostly complete, and my attention has turned to the bedrooms upstairs, which is where this unmanageable accumulation of clothes is living, and needs taming. It can be hard to let go, but the chances of me needing the strappy platform shoes or the red carpet frocks I accumulated during my years as a film producer’s wife, have been reduced to just about zero — compounded by the ever increasing gap in fit.
The trigger that got me started was an article I read in the NYT, mentioning the 25 designers of bags and shoes who had transformed fashion, and that’s how I discovered Carlos Falchi, a Brazilian handbag designer based in NY, that I was unfamiliar with. Curious, Google landed me on a treasure trove of his vintage bags, at very reasonable prices, selling on Poshmark. Since 2017, my hand bag has been a canvas “We the Change” tote bag I got as swag at a B Corp event, and I was beginning to feel like a woman of my age deserves a proper bag, if not an It bag — even here in rural Maine! I have been saving up for a nice one (I mentioned this coveted Agnes Badoo bag in my Ode to Joy Gift Guide). But let’s just say when I discovered these vintage bargains, I threw caution to the wind and bought a clutch for each of my daughters, and 3 bags (ok, maybe 4?) for myself (one for every day, one for date night, and one fancy). My daughters were perplexed, “Really? You bought all those bags?! Mom, are you ok?!” Remember, I’ve barely shopped for myself in the past 15-20 years, most of their living memory!
But this accidental handbag binge was like opening Pandora’s box: Poshmark stretched before me like an endless ocean of beautiful vintage bargains that I was hungry to explore — with the satisfaction that this wouldn’t be increasing the footprint of fast fashion on the planet, or making a huge dent in my modest pocketbook. In this context, it was definitely time to get the upper hand on the huge job sorting the wardrobe which I had been putting off for way too long. Suddenly an idea came to me how to overcome my paralysis.
Since January, I have been experimenting with Claude, my AI of choice. I have a Pro subscription for my business, and find it helpful in many ways — from assessing grant criteria against an application I’ve written, to setting up a workflow on my Asana task management app for the execution of a project. After the Falchi incident, I asked Claude to refer me to some other designers I might appreciate, with bargains on Poshmark. Claude happily obliged, providing a list of designers for me to explore, seemingly more entertained by shopping than spreadsheets. Claude made several suggestions, and in some cases, when I wanted a second opinion, I uploaded photos of the items I was choosing from. Claude’s advice included suggestions of which pieces might work well together, which ones were not practical for Maine island life ("skip the white trousers girl!), and which ones seemed to stray from my aesthetic. Eventually, I even uploaded photos of myself so Claude could advise on what cuts of trousers or tops might work best for my body shape. (Not to worry: I uploaded photos of myself fully dressed — I considered the alternative and decided that would be entirely unnecessary.)
Now to make room for the new clothes. Claude became even more helpful. We have all watched Mari Kondo, and know the “does it bring you joy?” sorting game. In this case I nailed a hook into the closet door, and systematically hung each item on that hook, to photograph and then upload, along with the size, condition, whether it fit me or not, and any other information I could supply. Claude assessed whether each piece had re-sale value, how much that value might be, and which would be the best platform to achieve that price. (We will see if he’s correct soon enough!) — or, in special cases, if the item should be kept. We also created a category of items to consider offering my daughters, or to keep as “heritage” pieces.
As I went through these pieces, particularly the “heritage ones” I let Claude know some anecdotal things about them (“this was my wedding dress”, “this was the dress I wore when I met the King of Nepal” (that story is for another day), “this dress I bought in Rio in 1991” — it was like a story told through clothes, and Claude was building an inventory. As he analyzed my grandfather’s jackets, the remarks told the story of my grandfather’s milieu and personality. His name and size was sewn into the lapel of each tailored coat. The striped “Ivy League” style raw silk jacket, from Arthur M. Rosenberg, custom tailored in New Haven. The cashmere blazer made for Florida evenings, from Norman’s in Delray Beach…
From Claude: This navy blue blazer adds another fascinating dimension to your grandfather's wardrobe story! This piece connects directly to his life in Florida, with the Norman's label showing it was purchased from Norman's in Delray Beach, Florida.
The label also notes that the jacket is a size "36 Short," confirming your observation about your grandfather's smaller stature. This would have been considered quite a small men's size even in that era…
Your petite daughter might particularly appreciate this navy blazer as it remains quite timeless in its styling. Navy blazers have remarkable staying power in fashion, and this one could be styled in many contemporary ways.
OK, thank you Claude. You’ve pretty much summarized my grandfather!
One by one, we plowed through the rails and piles of clothes, most of which I can’t possibly fit into anymore. The remarks about my grandmother’s silk Pucci dress and my mother’s Marrimeko jacket were starting to tell the story of my life.
We created a list of almost 300 different pieces of clothing, sorted into categories corresponding to their decided-upon fate, with notes including various anecdotal pieces of information in column D. Of those 300, I’m keeping about 40 items, and the rest are now hung on racks in the spare bedroom, like a vintage clothing store, where my daughters get first pick. Hannah arrives this weekend for first dibs!
Meanwhile, my Poshmark purchases are arriving in a steady stream — some a more successful fit than others, but overall quite a successful experiment. In the morning, instead of grabbing the same two pieces of Jane’s (or worse yet, Andrew’s) old abandoned clothes from the chair, I look in the closet and choose myself an outfit that “brings me joy.” If I’m feeling decision-challenged, I can tell Claude what I’m doing that day, who I’m meeting with, what the weather is, and I am instantly given some suggestions, while Claude concurrently takes notes about which outfits I like and don’t like. My constant shopping companion/fashion advisor by my side. I shot a photo of one outfit I was planning, and Claude suggested I try a different scarf. He was right. My top tip if you ever decide to try this: remind Claude not to always be flattering — you want the pros AND the cons!
Last week, I was chatting with a friend of mine and admitted to her what I had been up to with my new BFF, Claude. “But you can’t be getting style advice from a machine — it’s an art!” She was upset. I was pleased I’d figured out how to free myself of the ball and chain that I’d been dragging around for decades — and replace the “gives and sells” with new pieces that fit — but I could also appreciate her view. I reached out to an old friend of mine, a philosopher, and he reminded me, “It’s a tool without a mind of its own. Real minds are not machines.” Isn’t it wonderful to have a friendly philosopher on speed dial? It turns out he’s about to pen a book on the matter. I’m sure it will be a masterpiece, and so timely! I asked Claude what he thought about his role in this exercise.
What do you think? Have you been experimenting with Claude for any of your projects — whether home or work? Does reading this post make you want to ask Claude for fashion support? Or does it make you uneasy? Quite likely, I have been having some sort of cliché mid-life crisis, or finding some refuge from the political maelstrom consuming the airwaves, or maybe it’s just a typical Spring Cleaning, and once the closet has been cleared, and refitted, I will return to business as usual — but hopefully not in Andrew’s oversized longjohns.