The 3 Most Embarrassing Outfits I've Ever Worn (With Pictures!)

1. Red Pants + Cocaine: The Ryan O’Connell Story

I wore this outfit to my roommate’s 20th birthday party while I was a sophomore at San Francisco State University. In retrospect, everything I wore that year was 85% terrifying but this one takes the (birthday) cake. Red pants? A grey crew neck shirt layered underneath a grey deep V?! Holy homosexual! There must be only one explanation for this sartorial disaster: Cocaine. I’ve talked before about dabbling in Kate Moss during my early college years. Part of me feels like I should just keep quiet about it but the time I spent trying to do coke was so HIGHLARIOUS and strange, I can’t not share. (I’m not trying to be insensitive either. I watched a few of my friends get addicted to the stuff, so I know coke isn’t an LOL. I’m just speaking from my own experience.) I hated the stuff from the first time I put it up my nose, but like with most things, my learning curve was slow. It took me seven years of smoking pot recreationally to realize that I actually hated it and as a result, I haven’t gotten stoned in over a year. With coke, it was no different. I would try it, do two lines, and FREAK OUT for the next 30 minutes to an hour. It also took away my two great loves of eating and sleeping, so I knew my little dance with the drug would have to be brief. Coincidentally, the night I wore this outfit ended up being the last Coke Night I ever had. I bought some for my roommate as a birthday present and we ended up doing it in a spare bedroom all night and practically missing her actual party. That’s the funny/scary thing about coke. It all has to be done shadily. You want to sneak off to the bathroom to do it. You want to lie to your friends about doing it even if they don’t care. It’s an elitist drug that thrives on secretive behavior and exclusivity. After spending what we thought was half an hour but in actuality was most of the night in this stranger’s bedroom doing blow, my roommate and I finally emerged looking cracked out of our minds and posing for pictures. Thanks to Facebook, I will always have photographic evidence of me looking high as hell and wearing red pants. So thanks, Internet. Thanks cocaine. And thanks to whatever trendy hipster store that allowed me to spend lots of money on looking like an idiot.

2. “You know what would look really cool and chic? A velcro duck vest with white short shorts!” – SAID NO ONE BUT ME!

Um, yeah. I don’t really know what to say about this ensemble. I can’t even blame coke on it because I remember this being a total sober decision. I bought this vest that was made out of velcro from one of those DIY fashion vendors at Bumbershoot in Seattle. The clothes being sold there were sort of Etsy-esque but more freakish and gay. I still hadn’t learned the valuable fashion lesson that less is more, so when I saw something that looked insane, I just had to have it. From the ages of 15-21, I legitimately enjoyed looking like a freak on a leash. I thought it gave me character and helped me stand out in the crowd. It wasn’t until I came home to my dad’s house during a break from college wearing ten necklaces wrapped around my head that I realized something had to change. My dad took one look at my outfit and just said, “Ryan, don’t take this the wrong way, but you look like someone who’s mentally-challenged.” Way harsh Tai, but he was right! This whole look wasn’t really working out for me. A boy hadn’t touched my penis in nine months either, so I knew it was time to try a subtler approach. Thanks Dad for your cruel and insensitive honesty! (No, seriously, thank you!)

3. I’m wasted! Let me wear non-prescription sunglasses even though I’m blind and don a huge puka shell necklace!

Do you see that bracelet I wore as a headband? I wasn’t lying when I said I literally put anything around my head. I would put a dick around my noggin, so long as it resembled a hipster headband. In this photo, I’m also wearing sunglasses, which means I can’t see anything. In high school, I used to just wear sunglasses over my normal glasses, thinking no one would notice the lens peeking out. When I realized how obvious it was, however, I just decided to be blind and ditch my glasses entirely. During my freshman year of college, I would go to house parties wearing sunglasses indoors and get wasted, despite the fact that I couldn’t see two feet in front of me. I’ve never blacked out in my life but there are nights from freshman year that I can’t recall simply because I couldn’t see anything. And that, my friends, is FASHUN. Thought Catalog Logo Mark

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