Your Most Outlandish Fashion Disasters

New York Fashion Week came and went here in the big apple. For those of us who have strong opinions on looks but little talent or ambition when it comes to realizing them on their own fleshy forms, it’s mostly an excuse to talk about outfits without, you know, participating? Or is that just me? Lots of people had a great time at Rihanna’s Savage x Fenty show, whereas I had a great time looking at pictures of other peoples’ great time.

This year, Jezebel celebrated NYFW by joining forces with our sister site Deadspin for JezSpin’s Football & Fashion Week—a lawless and laughable good time where sports guys wrote about the clunky platform shoes trend and Megan dressed like some famous football man I’ve never heard of before.

This, naturally, has lead to a conversation about fashion faux pas: the good, the bad, the ugly, the innovative, the egregious, so on and so forth. I distinctly remember going through a lace fingerless glove/red and black tutu phase in junior high, which would have been fine if said glove hadn’t extended to my elbow, and if I didn’t demand to wear those tutus like, twice a week to school in 8th grade. In retrospect, I was doing the most, but I don’t think it was too terrible. In 2018, I might’ve even been embraced.

So… what weird fashion faux pas have you engaged with? It can be anything from a past adolescent indiscretion or something as recent as, well, today. One of y’all has to own croc high heels or the Prada flame shirt.

But before that, let’s get to the best, funniest and most heartbreaking responses to the last week’s pissing contest about your most memorable middle and high school breakups.

ThinWhiteDutchess was kind of an asshole but it worked out for everyone involved:

My first boyfriend was my junior year of high school. He was nice, really into vintage film, and told me I was pretty when I was having a rough go of it in high school (bullied bc of disability), so when he asked me out I said yes, even though I felt no spark. We dated for awhile, but then I met this guy at a house party who was gorgeous, into art, and sexy as hell. He and I stargazed (I know- lame) at the party bc he was DD, and I wasn’t drinking, and he asked if he could take me out sometime, I said yes. The next day I broke up with my boyfriend, on our date, and he cried, saying I had to kiss him and then look at him and tell him it meant nothing. So I did and then looked at him and shrugged, “nothing.” He took me home, and gave me a VHS (bc I’m old) copy of we’re no angels (an old bogart film) and told me to think of him when I watched it. Then he called me every few years until I got married to see if I was still “with that guy” (plot twist: I ended up marrying the hot party guy).

He is now married to a super hot babe and a successful chef in NY and they have adorable twins and a tiny baby.

Hillbillarincess did what we all fear to do, via six-word text message:

I had been seeing my high school boyfriend for a few years. After some reflection I decided it was time to end things and texted my sister “I’m breaking up with Johnny today.” But instead of my sister, I accidentally sent it to Johnny and I felt awful but also it saved me that whole sitting-in-the-car-in-front-of-his-parents-house-arguing-and-crying typical breakup convo.

Graceless but Gracious should sell the movie rights to her freshman-year affair:

My friends all felt bad for me at my 15th birthday because I didn’t have a boyfriend and they were all dating guys from this big extended family. So they set me up with this guy friend of theirs that night. We sat on the tailgate and held hands (and when I got some drunken courage I leaned in to kiss him and he fell off the tailgate). He drove me home from school once or twice, but I was madly in love with some idiot who didn’t want anything to do with me and I think I just dropped off the face of the earth on tailgate guy. I was a shitty human as a teen.

The most notable part of the story for me is tailgate guy had a super blonde, super popular sister who marched up to my cafeteria table mean girls style to interrogate me about my dating her brother. The reason I say this is notable is said blonde is now my sister in law and hates when I tell that story. Tailgate guy and I reconnected when I was 25 and have now been together nearly eight years.

YoucancallmeAL was not down with Doogie:

During the first two weeks of 7th grade I dated the “mysterious new kid” at school. He dumped me because I told him he looked like Doogie Houser, MD (he did). He had an obscenely large house for our small town. I know now that’s because his dad is the co-founder of one of the largest for profit prisons in the country. So fuck you Doogie, your family is gross!

I hope run, lillian! at least got a bloomin’ onion out of the deal:

He dumped me at an Outback Steakhouse on Long Island.
I think I win.

And anotherdayanothername’s romance might be the most quintessential middle school story:

In 7th grade I had been dating a boy since 6th grade and was getting bored with him. My friend and I made a “pro” and “con” list of continuing to date him. I think on the “pro” list was the fact that he had already bought me a necklace as a Christmas present and I wanted to get it. But I resisted materialism and made my friend call him and break up with him for me.

Wicket’s Lament laments that guy, who seems well-adjusted and fine:

In high school, I remember trying for hours to break up with a guy over the phone, and he would just talk over me or interrupt me, or just plain ignore me. I hung up wondering if he understood that I was breaking up with him. Then the next day he calls me to tell me he wants to break up.

I’ve never been so grateful to be old!

So, tell us, what’s your strangest/best/most fucked-up fashion look? Bonus points for pictures, if you got ‘em.