My Midlife Flirtation with a Stylist

Learning to dress myself

Photo by Julija V. on Unsplash

Maybe it’s lockdown, maybe it’s middle age. Maybe it’s just a continuation of the same conversation I’ve been having with myself since the slow slide to dishevelment began, back when the kids were little. I desperately need new clothes. I want a little style. What is my style?

Ah, that is the question.

I hate shopping. Nothing ever fits and the best things are too expensive. It’s exhausting, the lighting is bad, and I always feel like a rat in a capitalist maze. Online shopping is a better experience, but for me the success rate remains low. Shopping is a frustrating chore, except for in those brief carefree college days, when I rummaged through giant boxes of vintage at Classic Clothing, a featureless warehouse in 1980s Washington D.C. I bought some stellar pieces for pennies in those days, but almost none of it fits anymore. And where does one wear a 1940s black crewel fitted dress with velvet piping, anyway?

I have been living in thrift clothes and bargain threads for years and it’s been fine. My mother, an inveterate thrifter, brings me bags of second-hand finds (or used to, before the plague). I rejected much of it, but kept things that are close enough. Not quite me, but in the neighborhood. Throw in some seven dollar pants that feel great but are the wrong color, and cast-offs found at Naked Lady parties, and you have what has become “my style.” Whatever is at hand and comfortable, if somewhat hideous.

My style is not mine. What is free, or cheap, is often someone else’s style. I’ve been cobbling together the style of others to create a sort of slapdash look that is definitely cheap, always comfortable, and never actually stylish. Pre-kid, mine was a sort of anti-style. I went for artsy, unstudied, casual mess, which of course was a study in itself and required hours in a vintage warehouse and enough mirror time to comfirm that I looked unstudied. Anti-style is, of course, a style. No makeup, artfully holed jeans, and that amazing military jacket with the gold buttons from the bottom of a Classic Clothing box was its own uniform. Smash the patriarchy, but look accidentally hot while doing it.

I’m writing in a large, soft, orange cable sweater that I found in my nonagenarian mother-in-law’s closet. In a store, I would never select orange or cable. In a mirrorless condo closet, however, when you pull it over your head and realize it’s the most comfortable sweater you’ve ever worn, an embrace of effortless comfort, you won’t take it off. There are, however, mirrors in my house and I pass them many times on my endless lockdown circle route, the Great Pumpkin wafting by. It’s fine, I tell myself, because it’s so comfortable, and it is. Until it sort of isn’t. Until I start having that conversation with myself, so common in these middle years, about how I’m going to die and this is my one and only shot and maybe I don’t want to be remembered in orange. Intellectually, it doesn’t matter and I will fight this point all night. But something other than the intellect is sick of these clothes.

I’ve cared, but never enough to find my own style. Never enough to work on it. And so, I’ve decided to seek help making a wardrobe and finding a style using an online personal styling service. Here are my reasons:

  • I can’t go anywhere because there’s a plague.
  • I wouldn’t really want to go anywhere even if there wasn’t a plague.
  • I’m bored (plague).
  • I need a change, but can’t even get my hair cut (BECAUSE THERE’S A PLAGUE WHAT ARE YOU PEOPLE DOING).
  • I hate my clothes and, by extension, myself.

Given that this is the sort of thing I’ve made fun of, it should be interesting.

The service I’ve chosen is the cheapest, of course, because I’m cheap. For $20, I get a stylist to help me and, if I buy the clothes, that money will go towards them. What’s to lose? Only $20 and any hope that I will ever be stylish.

The first step is a quiz. It feels like a comic insult, answering questions about my style while wearing my uniform of torn separates. I don’t like any of the outfits in the quiz. I don’t know how to answer some of the questions (are my arms long? average?). I reject every category except casual (date night? evening event? what?). I have no idea what my bra size is and never want another bra. I pick the cheapest tier and have no interest in bags and accessories. I begin to worry that this is all a mistake, but then they ask me to write a profile. It’s my time to shine. I can tell them everything. I push the limits of the character count. I write, and re-write, and read it to my husband repeatedly. Body shape, size, style taste and budget. Then, I am given the option to share a Pinterest style board and Pandora’s box is opened.

Oh unsuspecting $20 stylist, you sweet summer child.

I am delighted to share my Pinterest style board, a collection of Georgia O’Keefe’s Brooklyn Museum clothes, Kate Hepburn playing tennis, Isabella Rossellini on the farm, Sophia Loren in the kitchen. Linens and silks and vintage, wools and tweeds, unstudied glamour. Of course, they are wearing O’Keefe, Hepburn, Rossellini, and Loren, none of which the stylist will ever find for me. It’s like the time I took a picture of Rossellini to a hairdresser and said, “I want this.” She looked at me unblinking for a minute and said, “but your face is a different shape?” Make me her never works.

I want ageless, timeless, classic and elegant. Make it comfortable, cheap, only natural fabrics please. Slouchy but chic, serious yet charming. Earth tones, but sometimes color — never orange, probably not white. I like the fitted look, but don’t want anything touching my body. I like it loose, but don’t want to look like a bag. I want to look fashionable but I don’t want it to be fashion. Style is a mood, a way of life, and I want one. Good luck!

I believe that my stylist, Kristen, is earnestly trying to help me and I love her. She uses exclamation points and talks about making me feel great about myself! She sent me a preview of suggestions after presumably looking at my quiz and my Pinterest, and I responded with detailed feedback.

Hi Kristen! These are definitely in the ballpark. I already have a berry hoodie and some plaid button downs. The burgundy sweater is lovely, but I’m picky about natural fiber tops (don’t like acrylic). I like the styling of the stripe sweater, but not the big stripes. The curved hem pullover is cute, but I worry about the fabric. I LOVE the cashmere pullover, though I’d prefer it without the turtle. I’m excited to try the Becca pant and the jeans (though jeans fit is a challenge for me). I’m curious about the jogger and I like the Artez pant, but not the light green. Maybe in a darker color? Thank you so much for your help — this is fun!

Is it, though? Is it fun? I haven’t heard from her in days. Maybe she hates me, I think at 3 a.m. Maybe this underpaid worker, with the job of dressing a lockdown maniac who wants throwback glamour for a dime and no work, hates me. Of course she does. My problem, which is now her problem, may be that I want the impossible. Comfortable, cheap, signature, classic, and unstudied. Study it and find it for me. For $20.

My husband thinks Kristen is an algorithm, but I think she could be my friend. My first box of clothes arrives later this week and, while I’m expecting the worst, I’m allowing for a little hope. I may send it all back and trudge on in my bad colors and torn pants, but maybe there will be one thing — just one thing, please fashion goddesses — that feels like this orange sweater, but looks like mature, confident beauty. I don’t really care. But, also, I kind of do.

Write it down.

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