Recently, we offered readers a chance to win this custom-embroidered and patch-adorned vintage Levi’s jacket. All they had to do was tell us, in 100 words or less, about their most regrettable fashion purchase. We received hundreds of entries confessing all manner of fashion mishaps. Some common themes: too-small shoes that refused to stretch, hopelessly uncomfortable “parachute pants,” clothing that proved droopy at inopportune moments—and the particular misery involved in wearing the unflattering color orange. Here is the winning entry, a story that stood out for its ability to combine pathos with the word “go-go,” plus the top runners-up and honorable mentions.
The Winning Entry
“It was the 1960s and my pathetic life was not worth living without my own white go-go boots. As a fashion choice, they were as practical and attractive as the miniskirts they went with. I had to have them. I spent my babysitting money on the cheapest pair available. Never mind that the soles were made of cardboard and that we lived in Oregon. Where it rains. The boots lasted three days. Then the soles deteriorated and mold set in. I wore them until they smelled so bad my mother made me throw them out. I still miss them.”
—Meryl Alcabes, Seattle, Wash.
“I purchased a wide-brimmed hat, such as the one Audrey Hepburn wore in a scene from “Breakfast at Tiffany’s.” I thought it completed my resemblance to the star. However, I am only 5’ tall and the hat was overbearing. As I walked into my office, my assistant said I looked like a mushroom.”
—Beatrice Gross, New York, N.Y.
“Crocs. I buy them. I wear them. I get shamed. I donate them. I miss them. I buy again. REPEAT.”
—Lana Kaye, Framingham, Mass.
“I was a third-grade teacher and, in the 1980s, I purchased a green cotton shirtwaist dress. When I wore it to school, I noticed that many staff members and students were saluting me when they passed by me. Later in the day, they said that they thought I was wearing a Girl Scout uniform. I never wore it again.”
—Marjorie Hauck, Amityville, N.Y.
“I once bought a pith helmet to wear in the hot sun for a summer of baseball games. I became ‘that guy’ as no one was wearing anything remotely like it. and people wanted to hear my British accent.”
—Paul McGillivray, Rochester Hills, Mich.
“In high school, I wore fishnet tights in nearly every color of the rainbow. It gets better—I wore tube socks over the fishnets with stripes the same color as the tights. On really special days, I put a fake flower in my red hair that matched the tights and stripes.”
—Emily Schall, Boston, Mass.
“A pair of black-and-white jeans. One leg was black and the other was white and I looked like an absolute idiot with two different colored legs running around in high school.”
—Matthew Natahusada, Long Beach, Calif.
“Working with a group of lawyers over a few weeks in the ‘80s, I noted that they all wore suspenders. Neat, I thought, but I was severely ridiculed for wearing both belt and suspenders. Needless to say, this engineer went back to just the belt.”
—Robert Ballard, Jr., Chester, N.J.
“1976. Not one but two leisure suits. One with actual rope for piping and the other with fake leather piping. What was I thinking? Oh wait, I was 18. I wasn’t! Leisure suits were ugly then and would still be ugly today. Guess that’s why I wear a real shirt and tie every day. Trying to make up for the 1970s.”
—Kent Jones, Madisonville, Ky.
“I still cringe when I think about the year of middle school when I wore bright orange bowling shoes every day, but I miss my blissful ignorance of style. Now I spend too much time analyzing what an item of clothing says about me instead of how it makes me feel.”
—Cal Gilmartin, Boston, Mass.
“Asking my wife Melanie E. Royce, M.D., Ph. D.—an always impeccably attired, beautiful lady—what her biggest-ever fashion mistake was. I quickly got a one word answer: ‘You.’ She refused to say why.”
—Stanton Royce, Albuquerque, N.M.
“Thirty years ago in San Antonio, I purchased the ‘last’ pair of Lucchese Anteater boots for $900. They were one size too small and torturous to wear. I could not get them enlarged for any amount of patience. I wouldn’t have bought them if the guy hadn’t told me they were the last pair I would ever find since the anteater had been put on the endangered list.”
—Matt Ahangi, Menlo Park, Calif.
“Anything and everything black, I look like I should be holding calla lilies in a coffin.”
—Marsha Holden, Hudson, N.C.
“In the 90s, I bought a belt from G-Star. Its belt buckle was a replica of an airline-seat buckle. My friends fell down laughing when they saw it. Bad choice.”
—James Burns, New York, N.Y.
“Calvin Klein parachute material, drawstring, three-quarter-length cargo pants. I thought they would be light and comfortable for relaxing weekend activities while providing lots of pockets to carry essentials. I ended-up carrying so much in the handy pockets, the pants always dropped no matter how tight I tied the drawstring. When I hit the hiking trails I was a frumpy and lumpy, instead of a chic nature navigator.”
—Tracy Miceli, Mahwah, N.J.
“A red Valentino dress with feathers, 40 years ago. I felt like a rooster.”
—Marlene Kohn, Aventura, Fla.
“Blaze orange fall Ralph Lauren jacket…I looked like I was moonlighting for the Illinois Tollway Authority.”
—Carl A. Steen, North Barrington, Ill.
“In the late ’80s, I spent a week’s pay on a glorious, white, full-length sweater coat. It had monster shoulder pads and a fierce hand-painted lion that prowled from the top of the shoulder to the hem. I was a wimp and just could not wear it. I gave it to a friend and regretted it for years.”
—Madeline Hyman, Pacific Palisades, Calif.
“One time I bought a completely basic T-shirt with black and white stripes that every person owns. I immediately regretted it because I love being different and having my own style. Buying that shirt just made me feel like I was as bland as everyone else.”
—Samantha Harkness, North Scituate, R.I.
“Cowboy boots with a speedo. Drop the mic.”
—Gregory A. Denton, Glendale, Calif.
“A prom dress that had a hoop underneath. It was so hard to sit down or go to the bathroom in it.”
—MaryBeth Wehbe, Bloomfield Hills, Mich.
“I grew up in a hardscrabble New England mill town in the ’60s and ’70s. Despite that fact, I somehow saw myself as a fashionista without knowing what that heck that meant. As a grade-school boy, I wanted white banana bell bottoms. Way ahead of my time. Only the girls’ department sold them. My mom nevertheless enthusiastically embraced my purchase. Those pants were horrific, particularly when matched with a green, faux-Roman medallion.”
—Steve Hirschfeld, San Francisco, Calif.
“A pair of red leather pants purchased at a shop on Rodeo Drive in the ’80s. Regrettable for who I was with when I bought them: the boss’s wife (a conservative religious woman). I felt she always looked askance at me at office events for the next 20 years. It made the joy of an exciting splurge feel like something I should hide. Haven’t worn the pants in years, but I still have them tucked in my closet.”
—Jo-Ellen Smith, Bellevue, Wash.
“A strapless, flaming red, lettuce-edged Stephen Burrows evening gown in the late-1970s. I didn’t regret the dress itself, but the way i bought it. My friend and I, starving junior Capitol Hill staffers, were invited to two White House Christmas receptions three nights apart, so we shared the cost of the dress, hoping to amortize the expense over the next five years. We were knockouts! But when my friend (second in the rotation) had it dry-cleaned for a spot of Champagne—ignoring the ‘Do Not Dry Clean’ tag. It came back to us at least two sizes too small. Neither of us could ever wear it again.”
—Candice Shy Hooper, Boca Grande, Fla.
“In my early 20s, I bought (and wore and wore) a rabbit-fur jacket that—with its generous hood and dangling fur pompons—made me feel like a retro-glam, mid-aughts Sonja Henie. The problem was that it was slowly shedding to death, and every time I slid off, say, some dark car upholstery, I left a ghostly silhouette in rabbit fur. Eventually I had to give up the coat, by this point named “Thumper,” when I began leaving Pigpen-style motes of rabbit hair wherever I went. Not long thereafter, I became a vegetarian.”
—Phoebe Kosman, Cambridge, Mass.
“A pair of casual pants with a Velcro fly opening.The first time I went to the men’s room, they opened with a ripping noise. Still have them, but only wear them around the house.”
—George Scheidker, St. Augustine, Fla.
“Without question, it was wearing a polo shirt inside another polo shirt in the mid-80s at college. The look was to match the color of the outside shirt’s logo with the inside shirt. What resulted was a cluster of too many collars fighting with too many colors!”
—Gregory Stewart, Carmel, Ind.
“These ridiculous, sequined, leopard-print, high-top Converse sneakers, a whole size bigger than what I normally wore, when I was a senior in high school. I thought they were ’so cool’ and that I would wear them all the time. I wore them once for an event and it looked like I had bedazzled clown feet. I never wore them again.”
—Melissa Barba, San Francisco, Calif.
“Well, I’m an Episcopal priest, and, as you may know, we Episcopalians like liturgical tradition and all of the fine fabrics that are used to construct the various ‘outfits.’ The cassock and surplice are the basic ‘ecclesiastically hip’ combo that is worn for fundamental priestly functions. When I was in Rome several years ago, I went into one of the hottest clergy-clothing stores to look around, and spotted a biretta! A biretta is a stiff, four-cornered hat, topped with a big, fluffy tassel, that can be worn with a cassock and surplice! Mistake! I looked like an eraser!”
—Father Nick Mezacapa, Rochester, Minn.
“I bought an evening gown from a secondhand couture website. It looked so interesting and elegant, but turned out to be complicated and confusing with cutout sides and fabric twisted in the middle. It was like solving a Rubik’s Cube and I could never figure out how to wear it. It’s in the box of ’possible Halloween costumes’ in my attic.”
—Jennifer Sanfilippo, Rochester, N.Y.
“I bought a very conservative navy blazer from Brooks Brothers and wore it to the office with khaki pants and a white collared shirt. Everyone asked me what activities I had planned for the cruise! Yes, I looked like a cruise director on ‘The Love Boat.’ ”
—Linda Salzman, Rancho Palos Verdes, Calif.
“A pair of nearly knee-high, lace-up Frye granny boots. I was 8 or 9, ‘Little House on the Prairie’ was the rage and Laura Ingalls Wilder did not have better prairie boots. Neither did Nellie Oleson. I tantrumed and cried to get this last pair, the Holy Grail of boots, savored them in the box, smelled their leather. But the shoes that I claimed would fit like a glove were both left feet.”
—Yael Lieberman, New York, N.Y.
“More of a regrettable fashion decision than a regrettable purchase, but here goes: In 1978, on the first day of seventh grade at a new school, I figured that wearing a pair of light blue ski pants just made sense. Mirrored sunglasses, a black turtleneck (tucked under the bib and suspenders, of course), and a pair of Pumas completed the look. I still remember getting a ‘have a good day at school’ kiss from my mom and the swish-swish-swish sound of the nylon as I walked to the bus. It quickly went downhill from there.”
—Jonas Lee, New York, N.Y.
“A bright red, pleather, fake Prada purse from a street vendor in Chinatown on my eighth-grade school field trip to New York. The label was slightly crooked, but I remember walking down the sidewalk that afternoon with it slung casually on my shoulder, thinking strangers might mistake me for a model. I had braces and was likely wearing tennis shoes and jeans.”
—Callie Clemons, New York, N.Y.
“I custom-ordered a black tulle tutu skirt from Etsy . I was very excited but I looked like an oversize broom. I wore it twice for Halloween.”
—Sophie Shuklin, Puyallup, Wash.
“It was actually an outfit I sewed in high school. I made velvet rust-colored knickers with a matching vest and hat. The vest was lined with floral fabric. I must say I was quite proud of my sewing ability. I thought I looked mighty spiffy (this was in the ’70s) until I wore it to school. I earned the nickname Captain Smiff and the students even made up a song to go with my new nickname.”
—Heidi August, Lynnfield, Mass.
“I interviewed for a senior executive position on an (all-male) management team. They flew me to an eastern resort to meet the entire team and determine ‘fit.’ The event was characterized as a dinner, but the invitation said something like ‘Gentlemen, wear jackets.’ Thinking they meant dinner jackets, I purchased a 3-piece, $2,000 St. John’s outfit —professional yet suitable for a formal dinner. When I showed up, dinner was a casual clambake-style roast on a very cold beach (the men wore winter jackets). Needless to say I was way overdressed.”
—Barbara Curry, Chesterfield, Mo.