Ever since Shailene Woodley wore those creepy “five fingers” shoes to the Golden Globes after party, I’ve been somewhat obsessed with them. What do they feel like? Is everyone as grossed out by them as me? Are they really comfortable enough to make someone reject the plethora of better options for workout wear and/or flats? I decided to try them out for myself.

First, a bit of background. Creepy toe shoes, or “barefoot running shoes,” as they prefer to be called, are designed to simulate the experience of running barefoot, like our physically superior caveman ancestors did. They also make your feet look like robot monkey feet. When I was shopping for mine at Paragon Sports, the helpful salesman asked me all kinds of questions about what activity I’d be wearing them for, to which I replied, “an article for a fashion website. Just bring me the ugliest ones, please.” Then I realized he was wearing the shoes himself, and felt bad. (Not that bad.)

I thought it would be fun to wear them to a fancy shoe party, and Michelle Smith was celebrating the launch of her collaboration with Sperry Topsider last night, so to tony Upper East Side boutique Milly I went. On my way there, I noticed two things: first, my feet were really cold. Vibram Five Fingers are not meant to be worn in inclement weather! On the upside, I guess they’re really well-ventilated. Second, I was very much aware of the ground, and the things on it. While I realize the shoes are supposed to make you feel connected with the Earth, the slimy streets of New York City are not really something I feel the need to connect with. I tread carefully, avoiding those nubby parts on the sidewalk that are meant to help wheelchairs keep their grip. Also, the ball of my left foot began to hurt almost immediately. Maybe I had the wrong size.

When I arrived, I got a glass of champagne and milled around. Nobody was talking to me! Was it the shoes, or the fact that I didn’t know anyone? Alienation set in.

Undeterred, I decided to try on some of the Milly for Sperry shoes for contrast. I asked a woman working at the party how I might do so, making sure to gesture down towards my feet. “Did you just come from a run?” she asked. “No, I just think they’re really comfortable,” I replied with a straight face, and part of me died inside. “These have a platform, so they’re really comfortable, too,” she said, pointing at her Sperrys. “We have them in navy, if you like that.” “Sure!” I said.

A saleswoman came over to ask me what size I was. “Nine,” I said, pointing down at my feet once again. Upon glancing at them, her eyes opened wide, but she didn’t say anything. A consummate professional.

I tried on the shoes she brought me and studied them in the mirror, carefully weighing these new “real shoes” against my barefoot Earth shoes.

“What do you think? Would you like to try on the other one?” she asked. I replied that they were too narrow for my wide feet (true) and I’d rather stick with something more comfortable.

I occasionally caught people looking at my shoes, but everyone was too polite to say anything. One fashionista in particular was giving me serious side eye:

Before I left, a friendly woman came up to me and said that she loved my shoes. “Do you like them?” she asked. I said yes. “I totally need some, I’m always running after my daughter.” I wanted badly to counsel her against them, but did not.

After that, I went to Ladies Night, a Thursday tradition some friends of mine have. “What the hell are you wearing,” asked my friend Jessica, and I explained my mission to her. I asked her to hold the face she was making for long enough to take a picture, and she obliged.

When we got on the subway back to Williamsburg, my friends asked me if I was going to take the opportunity to go home and change. “Why would I do that?” I asked. “I’m in this to win it. What’s the matter, don’t you want to be seen with me?” Of course they did. (No they didn’t.)

When we got on the L train, I tried to converse normally but my so-called friends kept breaking into small fits of laughter. “I’m sorry, I just can’t take you seriously with those shoes on,” my friend Amy said. “I like how you know it’s a joke, but you still can’t help being mean to me,” I observed. I wiggled my toes, agitating them further.

UPDATE: My friends wanted me to add that they were not laughing about my shoes in this picture, but a dream Jessica had in which it was literally raining men. Whatever, guys.

Eventually my friends forgot about my feet, and we had a nice time at local bar Daddy’s. More than anything we’ve been through in the past, these shoes tested our bonds of friendship and found them relatively strong, so that’s something. I’d like to say the road test is concluded, but I still need to try them out at the gym and on my boyfriend. I predict that the gym will suck and my boyfriend will still want to have sex with me (I will insist on keeping the shoes on), but who knows? Stay tuned for updates.