Wear Dare

The challenge: Go to the thrift store and pick out five of the most hideous, ridiculous outfits you can scare up for 50 bucks. Make your friend wear them all day, every day, for a week no matter what—no changing plans, no wussing out, and don't...

Mar 2 2009, 12:00am


The challenge: Go to the thrift store and pick out five of the most hideous, ridiculous outfits you can scare up for 50 bucks. Make your friend wear them all day, every day, for a week no matter what—no changing plans, no wussing out, and don’t explain what you’re doing either. In return, your friend tries to fuck your style up just as bad. OK? On your mark… get set… CLOTHES!

      Girl Challenger #1: Liz
I locked myself out of the apartment while walking my dog and had to trudge about a mile deep into Bushwick to my friend’s house, where my spare keys live. I didn’t have my phone on me and her buzzer was broken so I stood out there and screamed her name until someone in the building let me in. If I told you how many men called me “Princess” or “Precious,” you would become very depressed, as did I. Amy Kellner called me “adorable,” and she meant it sincerely. My therapist said the exact same thing, mostly because of the hat, which gave me very itchy hairline acne, boil-style. I felt flappy, pink, lost, embarrassed, and cocker-spaniel-y, all day long. Once I flushed a toilet two times in a row by accident, because I just didn’t know what I was doing anymore. At the grocery store I kept bumping into things and people continually asked me if I needed help. At the end of the day I decided to just give up. I bought a giant bag of barbecue potato chips and ate them on the train.   Girl Challenger #2: Jamie
It was my first official day as an unemployed person, so I slept until noon, then went to do some grocery shopping at the Food Bazaar by the projects. The dudes hanging out in front didn’t give me a second glance. Either airbrushed Looney Tunes characters are cool in the hood these days or I looked so crazy nobody wanted to fuck with me.

Then I went over to Bedford to do some job hunting. I inquired in a few bars and Subway. They all said no. Ran into an old friend from college. He knew me back when I dressed like a goth-punk cheerleader every day, so my outfit didn’t faze him. Over coffee, I cheated and told him what I was up to. He registered little surprise.

Later, I got my hair trimmed by a friend, who remarked, “What the hell are you wearing?” Maybe as punishment, she gave me awful feathered bangs to go with my outfit. I tried to be nice about it, but losing my job plus wearing awful clothes had made me extra-sensitive and I almost cried.

      Boy Challenger #1: Phil
I feel like with this outfit, Rocco was trying to bring my Asianness into the spotlight. This was the day of Obama’s inauguration, so I think a lot of people just thought I was being proud of my diversity. It was also my first day back at school, so I guess my teachers think I’m the weird kid now.

The truth is I spent all day practicing my posture and balance because that piece-of-shit plate hat wouldn’t stay on, even after I pinned it to my head. That thing is NOT a hat, no matter how the Goodwill people tried to market it. People in New York are used to seeing crazies and idiots, so I didn’t get a lot of reactions besides a few glances on the train or at school. But no one seemed to care that I was wearing a woman’s zebra-print jacket with some weird plastic all over it. The hat was the big deal. People at school asked me if it was a Korean thing and some little kid on the subway asked me why I was wearing a plate on my head, no joke. See? Even the kid gets it.   Boy Challenger #2: Rocco
I felt a little bit schizophrenic in this outfit. Not only did Phil decide to mix the jungle-man shirt with the red leather pants, I had to stick the Teletubbies-meets-Annie Hall hat on. I swear LL Cool J wore this hat in ’96. I looked like a dude who tells everyone he’s got a “killer bike” that’s really a moped with a lawnmower engine. The cutoff gloves pushed me from weirdo to total fucking creepo status. You know who wears tiki shirts, ass-suffocating leather bottoms, fruit-bowl hats, and punked-out fingerless gloves all at once? Child predators and Kid Rock.

As fucking hideous as the pants are, they’ve actually changed my life a little. I’ve been hearing a lot about what a nice ass I have! Seriously, no one even said anything about the hat or the shirt. But all these girls at work and on the street kept staring at my butt, and one of them even grabbed it. I also got some catcalls on my way home. I don’t know how I’m going to go back to wearing normal pants after this. It’ll never be the same.

      Girl Challenger #1: Liz
The most alarming thing about this outfit is that the skirt is a child’s size 10 and the waist is made to bubble out wider than the hips to catch a little girl’s blubber. Seriously, everyone, stop feeding your child garbage, then convincing the stuffed goose she looks like a princess by dressing her up in prancey skirts. You’re grooming her for a future of diabetes and unreciprocated oral sex. Anyway, after yesterday’s plunge into negative-zero low self-esteem, I realized if I was going to get through these next four days I was going to have to own these outfits and just be like, “What? I shop at Vampire Freaks, now go fuck yourself.” So I dragged around this vinyl mud flap and jingled like a dog collar all day long and behaved as if I were really hot because of it. I had to DJ at a “cool” bar, and to my horror my friends didn’t say a thing. I hadn’t given them any warning I was doing this, either, which means they thought this was how I naturally dressed myself for the day—and not only were they not surprised to see me look like I was rejected from both The Crow and The Matrix, they were OK with that.   Girl Challenger #2: Jamie
I went to Curly’s in Manhattan for brunch with my BFF. People often think we’re a couple because we kind of are, just minus the sex part. This was especially true today, because I was wearing mom jeans and two baggy shirts, and she was dressed really cute.

I shopped for taxidermy at Obscura, then back to Williamsburg to return some expensive shit a smooth-talking hot guy had coerced me into buying. As much as I would’ve liked to try hitting on him in my outfit, he wasn’t there.

By this point, the pants had started to chafe my vagina. I hoped this was due to friction and not some kind of thrift-store crabs they’d given me through my underwear. I stopped by the Vice office to see that Liz actually looked kind of hot in the clothes I’d put her in, that bitch. She then gave me some pigtails that made me feel extra-special. Like, “the older boys got me to blow them behind the bleachers by telling me it was a game” special. Perversely looking forward to getting to dress “sexy” tomorrow.

      Boy Challenger #1: Phil
Here Rocco put me in my “gangsta” look. This was the only shirt I wore that was not from the women’s department. But please note that in addition to the bedazzled necklace and unintelligible words, it does in fact say “OMG” on it somewhere. The hat kept my head nice and toasty, though.

I have this one class on Wednesdays where the professor’s a real har-har type and I knew he was going to have a field day with me. I walked into the classroom, trying to duck toward the back as much as I could. A friend of mine asked me what the deal was, and I flipped out on her, telling her to shut the fuck up before the teacher noticed. Class started and we were sitting there for a good half hour. I was thinking he was concentrating on teaching for once and I could get away shame-free. But of course, right in the middle of a sentence, he looks at me, and here it goes: “Did you find that hat in the trash? Didn’t you have a better hat? Is it at least keeping you warm?”

The next day I found my dog eating it.   Boy Challenger #2: Rocco
I think this was probably Phil’s worst work this week. This look just wasn’t that bad. The shirt is a little old-lesbian, but hey, at least it fit me, unlike every other shirt I had to wear. Apparently putting little guys in big clothes never gets old.

At least I still had the pants. Those things are the biggest confidence-booster I’ve ever worn. I walked down the street and, again, girls totally stared! I felt like I was in a soda commercial. I liked them so much I fell asleep in them when I got home from work. However, I stopped loving them when I woke up and my legs were so sweaty I thought I had pissed myself. It was even less fun when I had to take a good five minutes to peel them off slowly so I wouldn’t give myself some sort of weird chafe. But you know, after I hung them out to dry and they were back to their normal texture, I fell in love with them all over again. I’ll keep them for special occasions.

      Girl Challenger #1: Liz
After yesterday, today was a breeze. I felt like a fun babysitter, and all day long I wanted to cheer people up and sing songs and bounce around. Some guys even sincerely complimented me on this t-shirt, like they were impressed that I had such refined taste in superheroes. Ladies, here’s a tip: Wear an awful t-shirt of a comic book character and suddenly you’re a dick magnet.

At work, however, my bubble was burst when someone told me I looked like MIA, which is the worst insult I’ve gotten since some dude drove up to me as I was walking down the street and yelled, “Where are your tits?”

Otherwise, I felt pretty all right with this outfit. I was in my kooky jammies, you know? Nothing ever goes wrong in kooky jammies.   Girl Challenger #2: Jamie
I woke up and thought, “Maybe I’ll wear my blue dress toda—oh.” Donned my “sexy” outfit, then went to local clinic for a free HIV test. “I like your makeup,” my nurse remarked. “I wear it like that too when I’m not at work.” Waiting for my results was not nearly as funny as I had hoped. Everyone looked dejected and sick of having kids. Found out I don’t have AIDS, yay, then went to inquire about more jobs to no avail. Upon my return home, the cat freaked out and attacked my dangly skirt.

That night, I hit the Whiskey Pub in Tribeca. The place was full of bros in business suits. One of them grabbed at me as I squeezed past him and went, “Hey hey hey!” but he probably does that to all the girls.

Next, I stopped by the Levee, where a tall dreadlocked man kept whispering dirty shit in my ear. “You’re so sexy, I just wanna mmm!” I pretended it wasn’t happening until he went away. Ran into a male friend, who declined to comment on my outfit but maybe hugged me for a little too long.

      Boy Challenger #1: Phil
As soon as I put this on, I started to feel like an old tai chi master trying to adapt to life in the modern Western world. Someone told me I looked a little like Erykah Badu. I disagree, which is maybe why I ended up adopting a slight Asian accent and whispering that night when I was drunk and hitting on girls. I think at one point I might have even busted out some sweet tai chi moves when I was dancing with one of said girls. She was totally into it, I bet.

I must admit I really liked wearing the shoulder pads. I’m not really the beefiest of dudes, so it was nice to have that extra boost. Ironically enough, I felt more masculine than usual. At one point, I thought about cutting them out and putting them in all my shirts. But then I was talking to this girl, and she put her hand on my shoulder, being all affectionate, and was like, “Ohhh, what’s that? Are you wearing… shoulder pads?” Then she “went to the bathroom” and I never saw her again. Fuck Rocco.   Boy Challenger #2: Rocco
This was just embarrassing. I wasn’t wearing any pants (long johns aren’t pants) and I looked like a toddler who was dressed in his teenage brother’s hand-me-downs. And, I was freezing. When I got really cold at work, I would make like a turtle and tuck my hands and knees inside the shirt. My penis was hibernating all day. Five separate people at work thought they were being really creative with their zings and asked me if I forgot my pants in the morning.

I will say, though, after wearing this, I get why girls like wearing dresses. It’s definitely a lot more comfortable than pants, which can be so constricting sometimes. I felt like I was lounging all day. Also, when I went to the supermarket after work, I briefly considered the amazing possibilities of stuffing all my purchases into the dinosaur-size space under my shirt and running out, but I pussied out at the last minute.

      Girl Challenger #1: Liz
I now understand why people dress like nutcases and parade up and down the street. It’s fucking fun! When I went to get lunch, I was the wacky person on Bedford Avenue. People loved me. I got applause, I had my photo taken, people were smiling at me—simply by wearing hot-pink footie pajamas I was bringing joy into the hearts of strangers. Right after I got on the train, a stranger’s face lit up. “Ooh, you’re so cute,” she squealed. “I just want to squeeze you!” I told her to go ahead and squeeze me then, and she did. In a mere three stops she confessed to me that she’s a tango dancer who’s heavily into S&M and she thought I’d beat her up in a cute way. We exchanged numbers. I should’ve taken her home with me right then and shown her how my onesie unzips allllllll the way down to my ankle, but I was in a hurry. But now I know what to wear when I’m horny and want to pick up someone quick.   Girl Challenger #2: Jamie
As I walked up Union Avenue to the L train, the construction workers who usually shout gross things totally ignored me. I’d always believed catcalling was less about sex than closing a perceived power gap by asserting their ability to objectify you to your face, etc., etc. Maybe they do have standards after all.

En route to the store, I discussed the failing media with my recently laid-off friend. She stopped me midsentence with “I’m sorry, I’m trying to listen but I just can’t take you seriously looking like that.” Laugh it up, ho. Neither of us is ever getting a real job again.

Later, I went to retrieve my favorite bra from a one-night stand’s apartment. “What are you wearing that for?” he asked. Self-esteem flagging, I wanted to ask him if he still desired me sexually in what I had on, but didn’t for fear of attempted follow-through (or, conversely, of depressing answer).

Reported for a DJ gig at a nearby bar. The waitress tells me that the manager judges on appearance, and I should change. No dice. Grew increasingly hot, sweaty, drunk. Hardly anyone tried to hit on me. I could get used to the lack of sexual harassment.

      Boy Challenger #1: Phil
This was probably the worst day of all. Rocco was really into the texture combination, he kept saying some weird shit about the velvet and the felt blending together, which was worrisome. Anyway, I had a class that day where we go around to different galleries in Chelsea. Again, I got some stares and mini sideways glances, but no one outright said anything, until a girl in my class looked at me a little horrified and pointed at her chest anxiously. At first I thought she was asking for the Heimlich or something. When I finally realized she was trying to communicate that I was the one with the problem, I looked down, and there was a nice bright-pink rash blossoming right in the middle of my chest. I ran home and ripped the piece-of-shit velvet off and slathered on the Benadryl cream. I didn’t leave the house for the rest of the day. Fuck dirty old-lady clothes.   Boy Challenger #2: Rocco
This outfit was more Jazzy-Jeff-inspired, and the shirt was real Tommy Hilfiger too! I always get loopy at work on Fridays, and this was no exception. I caught myself slipping into the Jazzy character when I was strutting down the hall a couple of times. The pants brought out more of my grandma side. I imagined that these belonged to someone’s grandma, that she wore them right when she got out of the hospital and was feeling all cozied up. I was really feeling it when I had to change into my slippers at work because my shoes were all slushy and wet. Yes, I have work slippers. So, I was sitting there in my grandma pants and my slippers, all cuddly with my hot coffee mug, when my boss walked by and gave me a nice long evil eye. Whoops.

Another thing about the big shirts: Every time I was walking down a windy street, those shits caught like a sail and forced me back. This one in particular. I was walking down Broadway or another one of those streets that’s like a wind tunnel, and I had to really exert some force to move forward. I probably looked like an asshole too.

      Girl Challenger #1: Liz
It would’ve been real nice to end this experiment on a positive note but alas the helmet clunked around my noggin and slipped over my eyes and the train on the dress dragged a good foot behind me. The two times I left my apartment to walk my dog I felt like a superhero as the excess polyester fabric whipped around me in the wind, but I kept tripping on it inside, where I stayed all day to rearrange furniture and hide. I was invited to some crazy party inside an inflatable castle, but I knew if I went dressed like this I wouldn’t have a date again for the next two years. So I stayed in, waiting to be reborn again in the new tomorrow.   Girl Challenger #2: Jamie
Went to MoMA in shiny jumpsuit to look at art. My friends cracked up each time they looked at me. I realized this whole experiment was a bit S&M-y. I kept getting little emails from Liz telling me how to wear my hair, makeup, etc. Pretty soon we’ll be reenacting scenes from Secretary.

At a friend’s party later, people kept giving me compliments. One guy liked my futuristic vibe, another thought I looked like Grace Slick. My hairstylist friend was overjoyed when I told her she could have the thing once I was done with it.

Struck by a sudden death flu, I passed out in a friend’s bed after one drink. Woke up and rode my bike home, kept thinking I’d have to pull over and puke. Wondered if I could build a career as an ugliness consultant. Whenever a movie needed to make a cute girl really ugly, like Charlize Theron in Monster, they’d call me. OK, time to barf.

      Boy Challenger #1: Phil
Even though I didn’t leave the house for most of the day (still a little sore about my velvet-induced chest rash), I wore this outfit the whole time. I mean, it’s a lady’s pajama shirt and glorified sweatpants. I looked like an asshole, but it was pretty comfortable. In fact, these pants are the only thing I’m keeping. They’re good warm pajama pants for the winter even if they’re the color of baby diarrhea and the texture of an old dishrag you’ve been using to clean mold out of the sink.

The problem came when we decided to go out that night. My silky muscle shirt and Rocco’s pink-chiffon-and-mustache combo were like catnip to the eight guys who hit on us. Eventually we started telling them that we were together and they left us alone. It even started to become true, as the night wore on and the drinks got drunk. By the end of the night, there may or may not have been some dry humping on the dance floor. I’m blaming the clothes.   Boy Challenger #2: Rocco
Yesterday’s grandma feelings were nothing compared to today’s. If yesterday was comforting, warm-cookies-and-milk grandma, today was washed-up Mexican-telenovela grandma. The billowing flamingo-pink shirt on its own would have been enough, but when Phil paired it with the same fucking pants again I almost lost it. I got lucky when he let me wear a black tank top under it, which is saying a lot about how skewed my perspective on luck is this week.

I did my laundry and I got some looks. But no one said anything! I bet people thought I had run out of normal clean clothes.

Me and Phil went out that night, and of course we kept getting hit on by dudes. Whatever, I got a couple of free drinks out of it. One guy was more cautious, and asked if Phil and I were together before making a move. We realized they’d leave us alone if we told them we in fact were, so we did. At that point, I really started missing the red pants and all the girls that had come with them.
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