Choosing What to Wear

The real decisive moment


in Features • Illustrated by Bhavna Ganesan


I have my suspicions about nudist colonies. Nothing to do with hanky-panky, mind you. I’m just guessing that some residents have a secret reason for going au natural: namely, to avoid deciding what to wear. 

It’s the question we face anew every morning, a reminder that to live is to choose — perhaps the last thing we want to do before we’re fully awake. Granted, this choice weighs more heavily on some of us than on others. There are those who seem to copy the Eudora Welty character who dressed like she just opened her closet and said, “I’m going to town. Who wants to come along?” Then there are the more discerning dressers who would amend a famous Nietzsche quote: “To live is to suffer” — especially if you’re wearing the wrong outfit. 

The editors of the book Women in ClothesSheila Heti, Heidi Julavits, and Leanne Shapton — are clearly in the discerning camp. They are successful authors who happen to care and know enough about clothing and fashion to have generated a survey of over 50 questions “designed to prompt women to think more deeply about their personal style.” They also identified over 600 other women (mostly “writers, activists, artists”) who proved their own interest in the topic by responding to these “questions we ask ourselves while getting dressed every day.” The results of the survey form the basis of their book. As researchers, these three editors were almost as thorough about women wearing clothes as the Kinseys were about people not wearing any. 

As a man flipping through Women in Clothes, I at times felt like I was sneakily reading my sister’s diary and at others like I was rummaging through a strange woman’s dresser drawers — as when I looked at the photos of  Sadie Stein’s collection of 15 brassieres. But ultimately I realized the book was a rare window into the minds of people who take their attire even more seriously than I do. 

For example, I kept returning to three delightfully telling images interspersed throughout the book. The three editors titled this project “A Map Of My Floor”: outline drawings of the clothes each woman had considered wearing on a certain occasion but then discarded on the floor instead. I’m not unfamiliar with clothes on floors — I once watched, aghast, as my adult sons selected the day’s clothing from piles next to their closets — but a map of a woman’s rejects was new territory for me. And it struck me as comical to show discarded clothing in the type of schematic drawings used to identify people in a group photo, with each item numbered and described in a corresponding text. Most interesting to me were the idiosyncratic reasons the women gave for passing on the items, hinting at their style and personality. 

Like a good researcher, I tried to determine if this graphic evidence yielded any common themes in women’s dressing preferences. Some pieces of clothing were just plain wrong for the occasion, like the red-and-white mini skirt that Leanne Shapton didn’t wear on a film panel and the Commes de Garcons black tulle skirt that Heidi Julavits passed over for a funeral because it was “Too bleak-girl-at-the-prom. Too like I’m trying to perform, before an audience, my sadness.” Other “too” reasons for rejection were too: “preppy,” “suburban and boring,” “informal,” “Umbrellas of Cherbourg” and “sloppy.” There were also practical considerations: “Needs mending,” “stained” and not warm enough for the weather.  

But considering why the 37 items on the women’s combined floors were just not right underscores how idiosyncratic a sense of style can be. Why didn’t Heidi Julavits wear a knit wool dress with black and brown stripes to the funeral? Because it makes her feel “bouncy like Snoopy” and she can’t decide whether it’s “the best or worst thing to wear when one plans to cry a lot.” Leanne Shapton leaves a pair of shoes unworn on her bedroom floor because “they look like something my friend Trish would wear to work.”  Sheila Heti reports that she was all set to wear a thick, gray wool skirt with a silvery shirt when “a small voice in my head said, ‘Don’t wear this outfit.’” An astute arbiter of personal style listens to her intuition. 

Frankly, I was surprised to find only one instance when any of these women vetoed an item (Ms. Heti’s purple silk top) due solely to her mood. Some women I once worked with balked at my suggestion for saving time in the morning by selecting their outfits the night before. “How am I going to know what I’ll feel like wearing in the morning?” they shot back. Maybe our three-floor mappers were true professionals, objectively evaluating their clothing options to suit the occasion, like a political candidate choosing her words based on her audience.  

In fact, the most extreme dresser-by-mood I know of is a man, one “Mr. Le V.” as Max Beerbohm calls him in his essay “Dandies and Dandies.” Granted, this British aristocrat from the late 19th century enjoyed a much more leisurely lifestyle than the editors of Women in Clothes — and just about anyone else on the planet. Who else could spend the hours of seven o’clock, when he is woken up by “one of his valets,” to noon deciding what to wear?  

And what clothes-conscious yet harried 21st-century person wouldn’t envy the “perfect procedure of his toilet” as described by Beerbohm? After “he bathes, is shampooed, is manicured and . . . is enveloped in a dressing-gown of white wool,” he sits down to breakfast (“Leisurely he sips his chocolate . . .”) and reads his letters and newspapers. Okay, okay, you say, what about his clothes? But there is no rushing Mr. Le V.: 

With a cigarette he allows his temper, as informed by the news and the weather and what not, to develop itself for the day. At length, his mood suggests, imperceptibly, what colour, what form of clothes he shall wear. He rings for his valet — ‘I will wear such and such a coat, such and such a tie, my trousers shall be of this or that tone; this or that jewel shall be radiant in the folds of my tie. 

How does Beerbohm know all these details? Because he has been among the audience that regularly observes Mr. Le V.’s routine, along with his “many disciples, young men who look to him for guidance in all that concerns costume . . . themselves tentatively clad . . . to learn invaluable lessons.” Beerbohm and the other onlookers sat on a bench in Mr. Le V.’s dressing room, like teammates in a dugout watching their star pitcher throwing strikes. I imagine them cheering, carried away by admiration for a particularly trenchant choice: “Yes, the olive green cravat! Good show!” 

I had wondered whether the subject of clothing really warranted the encyclopedic approach and 500 pages of Women in Clothes. But then I read that Mr. Le V. himself outdid all 600 contributors to that book combined. For Beerbohm tells us that his admired yet obsessive dandy kept — “or, rather, the current valets kept for him” — a Journal de Toilette: a diary recording every detail of the outfit he wore on each day of the year. In 1896, the year Beerbohm wrote “Dandies and Dandies,” Mr. Le V. had amassed 50 volumes of his Journal

Beerbohm tells us that along with lined spaces for recording “the cut and texture of the suit, the color of the tie, the form of jewelry” worn each day, there was also a space for “Remarks.” If an uncouth bloke came across one of these spaces, he might have written, “Were your undies comfy enough for your balls on this day, Mr. Picky Pants?” 

My own approach to the real decisive moment is more casual than that of the women attending special occasions or a dandy with an image to uphold for his live audience. Since I’m retired, spending half of the day writing at home, you might share my wife’s benighted opinion that it doesn’t matter what I wear. But how could I possibly have the confidence to face a blank computer screen and write in my own voice if I wasn’t comfortably dressed in my own style? And when I eventually leave the house, just because I don’t have to do anything for a living doesn’t mean I can dress like anything goes. I’m fussy right down to my feet, which will never be clad in those clunky white “walking shoes”  that are popular in retirement communities. I must keep from slipping down the slope to old coothood.     

The outfit I’m wearing today — a hot, sunny, summer day in Wisconsin — typifies my taste. I’m writing on our breezy screened porch in khaki shorts from Prana, multi-pocketed like cargo shorts but, thanks to the lightweight, stretchy fabric, sleeker and better-fitting than baggy cargoes that look like they’re really meant to carry stuff. I have a lot of short-sleeved t-shirts — I avoid the word “collection” because it’s too pretentious — and many would go well with my tan shorts. I chose a light blue one printed with Rockwell Kent’s monumental illustration and art deco type for the cover of Moby Dickand not just because it’s “writerly.” I bought the same shirt for my son, Sam, who is also a fan of the classic and looks very handsome wearing it in a picture that my wife took, and I often decide what to wear based on the memories that clothes evoke. 

I try hard not to get up from my laptop too often, but when I do I like feeling my toes rub the smooth soles of my blue, rubber Birkenstock sandals (and recalling what a deal they were at just $35). The “Birkys” suggest that I’m just hanging out on a summer day and not really trying to write. That fantasy is as close as I come to writing fiction.  

Of course, I have to wear much warmer clothing around the house in winter, which seems to last about 18 consecutive months here in Wisconsin. That’s when I resort to the standard issue for retirees, sweatpants. But I only wear a nonstandard style, Uniqlo’s fleece pants with an athletic fit and minimal knee-bagging. They look pretty basic — black, dark green, navy — and the sky out my window is so often a grey area that I differentiate the days with a variety of artful, long-sleeved T-shirts. They’re also mostly from Uniqlo, part of the company’s collaboration with museums and other sources of graphic designs. So I can don a Mondrian on Monday, a torso-length giraffe from a venerable Japanese print company on Tuesday, and on Wednesday a page of avant-garde graphics right out of For The Voice, a 1923 classic of Russian Constructivism written by Vladimir Mayakovsky and designed by El Lissitzky. (When I first became enamored with this revolutionary book in 2000, if anyone told me I could one day buy a t-shirt sporting its artwork, I would have started saving up for it and learning how to contact the black art market. Yet Uniqlo’s shirt was just $19.50.) 

Before I leave the house, even just to go to the gym or the grocery store, I shed my sweatpants and put on a pair of Levi’s stretch cords. You’ve probably noted that I’m big on stretchy “bottoms,” the industry’s silly shorthand for both shorts and pants. In fact, I think adding spandex or elastane (longtime sources of stylish comfort for women) to the fabric of these men’s garments is one of the great innovations of the 21st century — right up there with next-day shipping. Levis or any type of jeans are just cooler than sweats (how many musicians wear those on stage?) and wearing the former in public signals you know and still care about that — even though you could park in a “Seniors Only” spot, which I avoid like Covid. 

I know some stoic, practical people rely on just one winter coat from November to April. So is my having almost a dozen warm jackets and coats excessive? Not when the cold, cloudy weather of a Wisconsin winter is so excessive. I rely on my diverse outerwear to provide mood-lifting novelty in this blah season, just as a chameleon changes colors to adapt to its environment. I always welcome the first day it’s cold enough to wear my oversized, patchwork, woolen Woolrich jacket with an insulated lining. It’s a variation on the old hunting jacket, styled for guys who only hunt for bargains like this gem I bagged 20 years ago. When sloppy “wintery mix” makes its debut in November, I reach for my water-resistant Burton skateboarder jacket of many-colored stripes. (I freely appropriate apparel designated for sports I don’t participate in as long as they keep me at the top of my dressing game.) Let my fellow Madisonians gripe about the inevitable sub-zero spell, their breath creating white puffs to punctuate their complaints. I stay snug and smug by rotating my long, navy blue wool overcoat, lined with toasty Thinsulate; a tawny shearling jacket (a $1,000 beauty whose price, after a number of markdowns, was whittled down to just $100), and a down jacket from Uniqlo in a rich plum color that upstages down’s mere practicality. 

When my wife and I are going out for the night or to a special occasion, I face a challenge that neither the floor mappers nor Mr. Le V. had to address: two partners’ parallel dressing. First of all, our “master bedroom” is so small that our king-size bed takes up almost all the floor space. It’s harder to choose an outfit when you’re worrying about your spouse accidentally elbowing you. Tossing rejected clothing on the floor, like the Women In Clothes editors did, wouldn’t work; it would take up precious floor space and might cause one of us to slip on a sweater or shirt.  

While sharing this mini-bedroom for over 30 years, I’ve learned some parallel-dressing strategies. Several hours before my decisive moment, say when I’m working out, I take a mental inventory of my closet and drawers. I’ll picture an outfit — like my red corduroy Levis, blue long-sleeved T-shirt embossed with a “vinyl” LP, and Clark’s natural leather ankle boots — and weigh how I feel about wearing it. (I have no need for a mirror; I prefer to picture myself wearing the outfit in my mind’s eye, not because it sounds poetic but because it’s more forgiving.) I may give the combo the thumbs up, only to recall that I wore one or more of those items when I was with some of the people whom we’ll be seeing that night. (These people often include our adult children and their partners, who appreciate my efforts to wear “cool” new clothes. It’s one of  the responsibilities of fatherhood not to let them down.) If necessary, I’ll make a quick adjustment (you’d be surprised how many shirts and sweaters I have that look good with red Levis), so that at zero hour I can grab my pre-selections and get dressed in one of the empty kids’ bedrooms — ceding the scant bedroom space to my wife. 

But whatever I might do to make this deciding time easier for her, I know my wife, Jan, won’t like having to “dress up.” That’s because what’s most important about clothing for her is always comfort and, in winter, warmth as well. Her black, ankle-length down coat has faithfully provided both for over a dozen years. When we used to have a dog, she wore the coat while walking it, with the puffy hood up, a scarf wrapped just below her nose and sunglasses. The only reason neighbors recognized her was because Tache was trotting along with her. That made me think of the Gertrude Stein quote “I am I because my little dog knows me, but in Jan’s case it was “I am I because they know my not-so-little dog.”  

My wife has made me well aware that finding “dressier” clothing that is also comfortable is much harder for women than it is for men. Yet she has a good eye for colors that complement each other and appreciates quality fabrics, so sometimes she steps out of her nothing-but-comfort zone and takes a chance on an item just for its looks. But then the first time she wears it, she’s likely to stand in front of the mirror and pronounce the kiss of death: “I don’t know about this new sweater” (or skirt or pants). Time to look for the receipt. 

Like many other sane women, Jan has problems with high heels. In fact, she gave them up for good after a trip to New York that I initiated. As part of my job at the time, I had arranged for Maurice Sendak to do some artwork for our catalog. Soon afterward, I was invited to a fundraiser for the children’s theater he was launching.  Since Jan and I are big fans of his, we were eager to go to the event, which occurred right before Halloween. Jan was anxious about choosing an appropriate outfit, and even wore heels in an attempt to fit in with the other women. 

To say she regretted that decision is like saying she is not a fan of Donald Trump. Although the walk from our subway stop to the fundraiser was short, the sidewalk was paved with cobblestones, which raised the degree of difficulty of walking in high heels considerably. I hoped that lending my shoulder for balance would make up for taking her to this obstacle course, but nothing could quell the outrage Jan felt once we arrived at the event. For it was hard to miss one tall woman’s outfit: a witch’s costume worn by theater board member Sigourney  

Weaver. “So I could have worn anything!” Jan likes to say when she tells the story to friends. Maybe we both should have come as two of Sendak’s Wild Things, so Jan could pad the monster’s big feet for comfort. 

Jan does have a few go-to items that I like as much as she does, such as a short, grey wool skirt she wears with tights for winter and a sleeveless cotton dress that has a white ground covered with sketches of endearing faces. I encourage her to get more clothing like this for sheer variety. I extoll the enjoyment of having a few favorites that always make you feel better when you put them on, making the decisive moment before any occasion a no-brainer. For me, it’s my long-sleeve navy T-shirt with embroidered white lightning bolts on the front and back; a lightweight, nylon jacket in the deep-sea colors of the ocean; and the Kapital brand Hawaiian shirt with images of disembodied blue jeans (the company’s original item) and women carrying cotton bolls mixed in with the more typical flowers. 

But it’s OK with me that Jan and I don’t have the same attitude about what we wear. Our almost 50-year marriage has flourished because we have other and some would say more important shared interests. Like literature, art, music, and buying clothes for two people who always look fabulous in them and never second guess our choices: our two grandchildren, ages two-and-a-half and four months. •


Stan Tymorek is a freelance writer specializing in the arts. His writing has appeared in the poetry website Jacket2, New Music USA, New York Public Radio's New Sounds, and Artenol, "a purgative for an ailing art world, a palliative for afflicted aesthetes," founded by the artist Alex Melamid. "Caught Dead In It" is one of a series of essays he is writing about the comedy in clothing throughout history, including the afterlife. He lives in Madison, Wisconsin.