006 | F!@# me t-shirts, floppy flower hats, and other style fails
Most of us don’t get dressed in the morning asking ourselves, Am I going to regret something about this outfit in five or ten years? And yet, nearly all of us have invariably looked back on certain things we’ve worn with some form of distaste or befuddled embarrassment. Sartorially speaking, fashion missteps are practically a rite of passage—even more so for risk-takers. Some of us, including writer Fiorella Valdesolo, look back on such style blunders with benevolence and amusement, while A Tiny Apt.’s Christene Barberich regards most of hers as learning experiences. Others cringe just conjuring up the memories. For this special edition of «Dress Codes» we asked a dozen or so considerably stylish individuals to share some of these particular moments.
Alors, to each their own regret…
In middle school I had this incredibly soft rayon button-down my grandpa had given me; it was brown, with red, orange and blue paisley. I loved wearing it. This was the era of platform thong sandals, and everyone in my school had the Steve Madden ones. I couldn’t afford them, but thought that buying an imitation brand in neon green would have the same coolness factor. One day I wore the sandals with the shirt together—with camel-colored corduroy shorts—and as I approached the lockers in the hallway, I could visibly see this boy laughing at me, before yelling something to the effect of, “WHAT ARE YOU WEARING!?!” I couldn’t go home, though I’m pretty sure I tried to. — Daniella Kallmeyer, fashion designer and founder, Kallmeyer
It was the mid-2000s, and I was obsessed with Nicole Richie's waifish party girl vibe. So when I scored one of those Alexander McQueen skull and jester scarves at the Barney's Warehouse Sale, it was destined to become a major, if highly questionable, fixture in my daily rotation. Was it chic? No. Was it effortless? Definitely not. Did Nicole have the same one? You bet she did. — Max McCormack, Communications consultant and writer
The year 2008 was definitely my fashion low point. Trying to fit in with LA’s Silver Lake hipster crowd, I wore oversized, thick-rimmed glasses, styled my hair in a shaggy side-part, thrifted from cheap second-hand stores, and sported a measly excuse for a moustache. I may not have been cute, but I was 24 and having the time of my life. — Patrick Janelle, founder, Untitled Secret
I used to cut my light acid-washed jeans at the hem to make them look flared so they would fit over my Doc Martens. — Sara Larson, founder, The Larson Project
In high school, I would attempt to layer pastel polos—for “special occasions”—and thought it was the height of style! — Zachary Weiss
I really regret not wearing high heels in my early 20s. I'm 6'1" and was incredibly self-conscious about towering over people (especially men—a fact that now makes me cringe). I often wore kitten heels as a compromise between my insecurity and the heel height I actually wanted to wear. No disrespect to the style, but it just isn't me. I'm a four-inch platform! It took a while, but I'm so happy to now be living my footwear truth. — Leah Faye Cooper, Contributing editor, Vanity Fair
With my formative fashion years being informed by early '90s sitcoms like Blossom, it's no surprise I was obsessed with the flower-adorned felt hat worn by the show's main character. I remember asking—or perhaps begging—my mom for one from the Limited Too, my favorite store at the time. She caved, and I didn't take this hat off—I wore it with everything from flowy dresses, to t-shirts and shorts, until I found a new fashion trend to hang my hat on (Guess Jeans, fluorescent tube socks, Mary Jane Doc Martens..the list goes on...). — Nandita Khanna, digital strategist and brand consultant
In college, I dressed in a way that today's kids might call extra—think vintage thrift shop garb and weird accessories. I loved to glue flowers and fake fruit on straw hats and wear them out. (I got called Blossom a lot.) While these hats weren't necessarily fashion fails, one wide, flat-brimmed number with faux grapes affixed to the side of the crown played into a memorable fashion fall. The day of this incident, I had on a floral 50s house dress, high-heeled clogs, and the grape hat. Walking between classes in one of the busier main parts of campus, I lost my footing and fell off a steep flight of stairs, and into a small bush—bare legs and arms akimbo. To my credit, I got right up, put my hat back on my head, and clopped off to class, never making eye contact with anyone. I'm sure no one noticed, right? — Libby Callaway, Principal and CEO, The Callaway
When I was a senior in high school, I cut these stretchy exercise pants off at the thigh. I then took the ankle end and slide them up towards my armpit creating a bell bottom sleeve. Actually, this isn’t a regret! This sounds super fun! — Johnny Cirillo, photographer, Watching New York
Cowboy boots on their own are no fashion faux pas, but they are when you pair them with teeny, tiny denim shorts. That was (is?), unfortunately, the unofficial dress code of Texas country concerts at the time. — Camille Freestone, Style Editor, Coveteur
I have plenty of past style choices that I look back on with amusement. College was full of them like neon whale tails and the vintage eyeglass frames I insisted on wearing even though my eyeballs didn't require them. One that really looms large in my fashion memory bank is the shrug. I, admittedly, owned a few, but one in particular—black with a faux fur neckline—got a lot (A LOT) of traction. It provided no warmth or actual coverage of my body and was made of a material that was surely flammable but I wore it out. — Fiorella Valdesolo, Freelance writer and WSJ Contributor
I try not to have regrets when it comes to fashion and style (or life, really), because each misstep sort of teaches me something new about what works, and what doesn't...even if it makes me groan. But if I had to pick one, it would be wearing super-high or tricky heels during fashion month, running around between shows, all over the place. I mean, wtf was I thinking? I look back at photos from Paris or wherever I was and see myself in these bonkers heels, and just think, ‘God, how much more ease and joy I would have had in those beautiful ebullient cities if I had just worn slightly more comfortable-but-also-cool shoes.’ Lesson learned. — Christene Barberich, Advisor, and Founder, A Tiny Apt.
My biggest fashion fail was a t-shirt that featured a phrase in French that I never bothered to google. I loved it and wore it constantly. One time a blog was taking a photo of me while I was wearing it so I stood there proudly smiling in my white tee. When the photo came out I was told that it translated to “f-ck me.” — Alyssa Hardy, author of WORN OUT: How Our Clothes Cover Up Fashion's Sins
In the spring of 2018, I fell prey to the beguiling chunky sneaker trend. A year prior, Demna Gvaslia had unveiled the Balenciaga Triple S, and I was itching for a close second. With a few dupes from ASOS and Eytys, I briefly flourished under the illusion that they made my legs look more slender—and they may have…but at what cost? For the next six months, my poor feet looked like misshapen loaves of bread. — Shyam Patel, writer/editor