What’s The Biggest Fashion Risk You’ve Taken?

On the heels of Paris Fashion Week and in the wake of our finally returning to functioning like humans and not fashion robots, the flood of street style images that have been inundating our browsers and brain-feeds beg a really important question, prompted by photos not unlike the above, which features one girl in green hair and white goat trim.

So, what’s the biggest fashion risk that you’ve ever taken?

Now, I’m not sure if you’re wondering where my response falls but I’ll offer it anyway. I think the biggest fashion risk I ever took was the first time I paired skinny jeans with a t-shirt.

Lol. Just kidding. Lol again.

Looks like I left my sense of humor in France, eh?

As far as previous pursuits can go, the dumbest risk I’ve ever taken was in high school when I cut myself bangs and looked like a cross between Justin Bieber and a human mop (which come to think of it, is just one entity, isn’t it?) for all of three months before they finally grew long enough to stay tucked behind my ears. The biggest risk I’ve taken was probably this one time when I wore black and white argyle socks with leopard print sandals, a pair of cropped green polka pants from Topshop, under a yellow peplum-style skirt by Miu Miu and a grey sweater.

I’d put it together for Man Repeller but never ended up wearing it for the site — just for dinner with my tight knit social circle (grandparents and parents) who gawked. In my opinion, I looked like London which, as far as I’m concerned, made the outfit a bona-fide score.

On a related topic that begs another question I’m going to ask: earlier this week I wanted so badly to pair a mid-length full red taffeta skirt with a grey cashmere sweater, ripped skinny jeans and heels. Admittedly, I’d culled the inspiration from one Yasmin Sewell who looked absolutely breathtaking doing just that at the Chloé show in Paris with a black skirt by the label, frayed jeans and a green satin blouse.


When it came time to test drive the trend myself, did I do it? No. Why? Because I felt like a copy cat which also elicited a sense of self-consciousness. It was really lame. This got me thinking about all the outfits that could have been, swimming in an abyss that now seems unreachable. Those outfits are like ships that have passed in the night just by virtue of our fashion balls refusing to drop.

Consider my stint with the anterior an imminent fashion risk I — mark my word — will take in the near future. But now I ask you — do you have any of those, too?

So, just to summate, there are two questions you have to answer: What’s the biggest risk and what’s the biggest regret? I have to know. Absolutely have to. Go, go, tell me, go!

  • Heidi

    Way back in the day (yes, I’m dating myself here) metallic Airwalk sneakers were all the rage. I begged, pleaded, and begged my parents to get me a pair for the first day of school. Of course all the cool kids wore one particular design and in one color. I couldn’t be just like them so I got a high top pair in metallic gold. Within 2 seconds of being at school they were dubbed my “Moon Shoes” and I actually destroyed them just so I didn’t have to wear them again. My parents were not amused. I definitely regret those shoes. I don’t regret having something different, instead I’m pissed that I tried to go with the crowd so much and ended up wasting my parents money on shoes that did look ridiculous.


    • alejandra

      those shoes sound dope.

  • Neens

    Might have been the time I cut my very thick, very blonde hair to a faux hawk and died in various shades of pink. I was 13 and looked like i was wearing a tiedie helmet.

    • Leandra Medine


  • Kelsey

    Sumo wrestler graphic tee, jean vest, black pleated shorts, and a pair of cow hide boots (complete with a square toe and wooden heel)

  • Tinsku

    Bacon patterned leggings and a fried egg hoodie. I had a theme but making it happen nicely….

  • Raquel

    Black long wig, sequin dress, pillow stuffed in dress around my bottom half (channeling Kim Kardashian pre-Kanye.)

  • Maddie

    I think my cropped Primp sweatpants that went just above the knee, adorned with brown rhinestoned bunnies, and my knee high blue Uggs. I’m not sure if it was the outfit or the 2 inches of skin that showed between the Ugg and the pants that kept heads turning. I tried to keep it conservative!

  • Meredith

    Cow print leggings. Never again.

  • Leili

    Probably the one time from high school in Iran. I remember one time at night I wore a short tartan skirt on top of short cargo pants paired with boxing shoes. I was also wearing a wool hat instead of scarf which during the time seemed a weird thing to do in an Islamic country where everyone wears either a chador or scarf/long coat. With all of that craziness I opted for a simple dark grey bomber jacket. One guy who saw me on the street dressed like this said A’udi billahi min As-shaytan il-rajim which is an Arabic term from the Quran which means I seek refugee from Allah from the accursed Shaytan! My male cousins were afraid to go out with me. They kept saying the religious police are going to arrest you but I never got arrested (just got several warnings).

  • Sam

    I once bleached my very dark brown/black, very, very curly hair and after it turned yellow/orange and brillopadesque I left it and wore it as an afro.
    Often paired with jeans and a knee length black skirt and a Fall Out Boy hoodie.

    Highschool was a weird time for me.

  • Lucero

    Silver pleather bell bottoms, white sequined tee shirt, and white platform sneakers, paired (of course) with crimped hair and bad bangs. For the first day of 7th grade. In 2002.

    Good grief…

  • Katie

    When I was a kid I wore 3 dresses laid over each other at once. I haven’t done that since but it worked… 🙂 In middle school I wore baggy jeans and sweatshirts and tennis shoes everyday. That was my biggest fashion fail or coming to school thinking I was trendy when I cut a top so my cami would show through and it just looked cheesy. Thank goodness those days are over…

    But my biggest fashion win was buying the big white flower from the first Sex and the City movie and wearing it to almost every class in my undergraduate career. My boyfriend first spotted me wearing it in ancient history class and the rest is history. Score!

  • Neekoh

    Cut my hair about 10 inches just because I was inspired by a blogger (wow, I can’t even believe I spelled that out). Before: http://www.livelovela.net/2010/06/barracuda.html and after: http://www.livelovela.net/2010/08/you-used-to-hold-me.html

    The grow-out is still in process, but I plan on doing it again some day.

  • Liz

    Middle School: Argyle socks, short flair jeans, brown birkenstock sandals, yellow sweater vest. I was dubbed the preppy mountaineer by the kids in band…yeah the kids in band were making fun of me. Low point.

  • Rebeka Osborne

    I went through a period of denim (or pleated) mini skirts with leg warmers and flip flops in high school. I’m still judging myself for that one.

  • Daniel Lautrec

    Risk: A few years ago, I was in Montreal and my friend and I were going to a Chromeo show. I opted for high shine, pleather leggings teamed with basketball sneakers, a disintegrating Metallica shirt that was once worn by my older sister in the mid-80s, a denim vest, and (obviously) a studded belt to tie it all together. Aside from the ‘Robin Hood: Men in Tights’ syndrome, it wasn’t too terrible. And I definitely looked better than the guy being walked down Rue Berri dressed as a dog.
    Regret: Laceless/slip on sneakers paired with bootcut jeans (that were torn to hell) throughout most of my tween years. Still embarrassed.

  • Wilted Orchids

    Not to be a jerk, but there is a misspelled word. You have, “grey” and I believe it is supposed to be “grow”. fyi. xoxo

    • Amelia Diamond

      grew! thanks!

  • Amelia Diamond

    pink ombre’d hair (in a non-cool way) bondage parachute pants and platform combat boots. omg.

    • Charlotte Fassler


    • Raphaëlle Lavielle

      Bondage parachute pants mouhahah! I remember a fried of mine had pink ones…

  • LEC

    I once bought a cropped silver/beaded bolero vest and wore it over a black tank and black pants… to Yom Kippur dinner…

    It did not go over well when my cousin exclaimed (and still brings up the time) that I was wearing a boustier to Yom Kippur.

    It. Was. A. VEST.

    …and I liked it….and wore it to a supper club later that evening.

  • Carly Jugler

    I mean…I don’t know if this is a “fashion” regret per se. But I had very orthodox Mormon parents growing up who refused to buy me thong underwear. So in the 8th grade, in order to impress my more skanky, experienced, and pantylineless friends I cut my own thong out of regular underwear (grannies panties as they were called then). They were a loose-crotched disaster and I ended up throwing them away to hide them from my parents.

  • Millie Cotton

    camo octopus trousers and sneakers with wheels attached. They were ALL the trend ten years ago in London, okay. Why??

    It’s a LDN Thing

  • Lucie B

    Biggest regret was trying to go blonde (I’m brunette, best in cool colors.)
    Biggest risk was also my best and most lasting. About two years ago I shaved one side of my head, dyed the rest black with a silver streak a la Dave Vanian, and grew it long. I have hardly gone a day without a compliment since then. It’s started many a conversation at a party, gotten me dates, and more than once I’ve heard “I knew we’d be friends the minute I saw your hair.”
    As Rick Owens says: “Hair and shoes say it all.”

  • Andrew

    I showed up, in 8th grade, to science class in a pair of Phillip Lim trompe l’oeil pants from his fall 2012 menswear collection. They had flaps on the front that made it look like I was wearing shorts over my pants. They were brown with small stripes of silver and beige, and they were made out of wool. I was so in love. I saved up for them all year and bought them half off on ssense. Alongside everyone else, I stuck out more than Karl Lagerfeld at an NBA game. And I felt weird and sort of uncomfortable, but then it passed, and I went back to my love affair. I still wear them, and they’re still super fucking weird, and I still love them.

  • Hudson Berry

    Nubby, fuzzy, 90s, violet/purple cropped long-sleeve sweater from Limited Too. I wore it last summer on a date. It got me a boyfriend.

    You gotta risk it to get the biscuit.

    Shoutout to the uni-boot, though. I was totally sitting front row at Louboutin and saw it close up. So, as Janis Ian would say, suck on that.

  • Allison

    Hair Chalk!

  • rach xoxo

    In eight grade my aunts bought me a Gap kids pair of black capris and a long puffy red ski coat. Both were not yet popular. Kids kept asking me where the rest of my pants were. I also got nicknamed the michelin man because of how puffy and long my coat was. I think I stopped wearing the capris until they came into style a year later, which is really too bad I was way ahead of my classmates. The big coat however I loved so much I wore it as many days of the year I could. And, i learned to love the michelin man comparison. He wished he looked that good! lol. In hindsight, that jacket was way to big and puffy for my twig like frame.

  • Raphaëlle Lavielle

    Buffalo platform sneakers? But they were so hype bakc in highschool.

  • pinkschmink

    I once owned glitter jelly wedge sandals, a spray-on knit strappy dress with feather trim across the bust (HUGE feather trim, like one of those fancy dress feather boas, but over the top of my not-insubstantial chest), and a leopard-print faux fur bomber jacket I found in a thrift store that looked like a number of stuffed animals had been sacrificed to create it.

    And then I wore them all together. With frosted orange lipstick, as I recall.

  • Cassandra Vallée

    I died my hair black with red highlights (no kidding), with plaid baggy pants and a punk band t-shirt. In highschool. lol.

  • Charlotte Fassler

    When I asked my cool babysitter to bob my hair the day before picture day.
    You know what’s not cool? a bowl cut. to remember. FOREVER by way of wallet-sized images.

  • Nicole Zimmerman

    Short maroon hair circa My So Called Life with purple Doc Martens and Khaki Overalls. Junior High.

  • Mojo

    Two days ago: floral top with plaid pants. Manrepeller, I hope you will do a post on how to combine this season’s fabulous plaids with florals, and with more plaids on top of those!

  • Ariana Estrello

    When I was 17, my younger cousin had a quinceanera (the Hispanic version of a bar mitzvah) and well instead of wearing one dress, I decided to layer two dresses on top of each other. At the time layering was very new and my very Hispanic family thought I had lost my mind for hiding my budding figure with this “layering” method Hispanic girls tend to stay away from. The bottom dress was a light gray, strapless bubble dress (with a skirt like the one Oscar De La Renta is doing) the dress I put on top was a patterned dress that also had a bubble flair. I looked like a cake, but in my opinion was the chicest American girl in the room (the party was in Mexico).

    P.S. I was the outcast and according to my family no, one asked me to dance, because of my dress. I apparently was already manrepelling back in 2008 and had no, idea.

  • alejandra

    I was really into bodysuits and dressing like lady gaga in general two years ago. I wore fishnet tights with thigh high boots and a longsleeve black lace body suit. Then on top of that i wore a giant vintage leopard fur jacket and a huge hat.

    • alejandra

      OU i also one time wore a headband I made out of cigarettes. chic.

  • Kyrstin

    When I was in high school, regardless of my outfit make up, I would tightly wrap a bright red hand-tied bow around my neck and pair it with matching bright red lipstick. I remember wearing it with a Pink Floyd “Dark Side of the Moon”, quarter-length top, and over washed Levi flares. People always commented on how I liked to indulge in weird fashion phases, but I eventually stopped wearing the bow because I kept choking myself from time to time, ha! It hurts to be beautiful?