A Fashion Dirtbag Goes Undercover at Vanity Fair’s Best-Dressed Party

Jason Wu and Diane Kruger. Photo: Paul Bruinooge/Patrick McMullan via Getty Image

You know those dreams where you’re doing your normal everyday tasks but you’re also naked? That’s what it feels like to wear a dress with only one sleeve. I had never worn a dress with only one sleeve until Wednesday night — I had hardly worn a dress with two sleeves on a Wednesday night — but on the occasion of Vanity Fair’s International Best-Dressed List party on the newly renovated fourth floor of Saks Fifth Avenue, it seemed only polite to forgo an arm’s worth of Spandex-y material in order to appear like I hadn’t accidentally stumbled into the building like a rube. Two sleeves were for losers; one sleeve was for a woman who has certainly at least been near a fashion party before.

Almost instantly, I regretted this decision. When I boarded the elevator at Saks, next to me stood a gorgeous woman wearing a suit and sneakers. She complimented me on my dress, and in order to not appear ignorant — is there a word for a suit worn by women? a sloot? — I replied, “I looove this,” and pointed. What I meant was: You look comfortable. The suit and sneakers were a somewhat last-minute choice, she said. On the elevator only a floor away from the party, I wondered if I too could make a last-minute choice to change into a suit. Should I knock out this perfectly nice elevator operator and don his? Probably wasn’t my size but —

— there was no time. The doors opened to the newly renovated fourth floor of Saks Fifth Avenue, and there were celebrities waiting to talk to me literally everywhere. Just kidding — I barely recognized most of the people in the room, but they all looked like they could be celebrities. So many blowouts and so much lipstick and an entire infantry of men in suits with nude ankles. There was not a single sock in sight.

Earlier that day, I made sure to have someone check the tag of my dress to remind me “who” I was wearing. I hadn’t even gotten into an Uber before I promptly forgot this information, and perhaps as a reaction, I then forgot to ask these maybe-celebrities the same question when I approached them surreptitiously like a silent sniper from behind, which I know is standard protocol for addressing celebrities at a fashion party. Instead, we chatted about what was on the forefront of my mind: how to be comfortable when you are professionally obligated to wear something other than jeans and a T-shirt.

Leona Lewis, whose name I first remembered from a Kanye West song and then remembered from her starring role in Cats, told me if you want to dress comfortably, you must stay true to yourself. “Everyone’s unique. If you try to really follow fashion trends, you’re kind of chasing. I feel like when you’re comfortable, you’re more confident, and that makes you look stylish, anyway.” I responded by asking the obvious: What if you don’t feel like putting on nice clothes in the first place? “If you’re not in the mood, don’t go. Stay home and watch Netflix.”

I silently regretted not having met Leona Lewis four hours earlier.

One thing I definitely remember about the Vanity Fair International Best-Dressed List party is that it was well-lit, which I have to admit I wasn’t prepared for. A dirtbag dressed for an undercover assignment is better equipped to ballyhoo the rich and famous when the room is dark and no one can tell that you are not actually picking up your high-heeled feet, but simply shuffling them across the slick marble floors like a slug in the wild. Under the unforgiving lighting, I sneak-attacked Gayle King as she waited for her photos to print from the photo booth. “Gayle,” I said, “how do you dress up while also staying comfortable?”

“I love a gorgeous dress,” she said, which was not the answer I was looking for. “The Vagina Monologues says, ‘What does your vagina like to wear?’ and mine is always a beautiful gown,” which was the answer I was looking for. “If you can get something long, then you can start off with great shoes at the beginning of the evening, and then at night, you can put on comfy shoes. I like that.” This was monumentally useful advice from Gayle King. I thanked her and proceeded to pet a woman’s tiny fashion dog, which she had brought along to the party. “We charge five dollars!” her male companion said to me, jokingly. (I would have paid him five dollars if he were serious, so a pretty bad joke overall.)

Diane Kruger, Jason Wu, and Kit Harington-from-behind stood cheerfully gabbing in a cluster of very good-looking people while I accepted a mushroom-risotto pastry puff from a server who was as attractive as Leonardo DiCaprio in the ’90s. It didn’t taste good, but I barely noticed; I was too busy taking note of the fact that Kit Harington was as short as everyone says he is. When he turned around, though, I learned that this wasn’t Kit Harington, but someone else entirely. There is more than one surprisingly short man in the world: one of many lessons I learned that night.

Regardless, I felt it only reasonable, after staring for so long, to approach Diane Kruger, a woman who is so good at fashion that even I know she is good at fashion. I asked what she thought about comfort-dressing for fancy occasions. “Just go simple. A black column dress,” she told me. Does she ever feel uncomfortable on the red carpet? Surely, she must. “I don’t really care if I’m comfortable on the red carpet or not. It’s such an extraordinary situation. I can be comfortable my whole life, so I don’t care.” Kruger said that she had recently ordered a cashmere onesie online. I applauded her on this purchase.

The only face that put me at ease that evening belonged to Bruce Springsteen, who, thanks to being the cover star of the latest issue of Vanity Fair, was literally everywhere I looked. Put down a glass of Champagne on an end table: Bruce. Hide behind a rack of bandage dresses: Bruce. Consider collapsing onto a settee and demanding someone re-sew the arm back onto your dress: Bruce. For a moment I tried to imagine Bruce Springsteen attending the Vanity Fair International Best-Dressed party, but I couldn’t conjure an image of Bruce Springsteen wearing a suit in my head. The cover line on Bruce Springsteen’s issue of Vanity Fair is “BRUCE!”

“SUIT!” I whispered, thinking his image might come to life from the glossy page, arriving at the party fashionably late, dressed sharply in a suit. But Bruce just continued to smile blankly from his motorcycle. His expression never changed, but I could tell he thought I was a sucker.

As the night drew to a close and I waited to retrieve my tote bag from coat check, I spotted Monica Lewinsky out of the corner of my eye. Relieved to see someone I might be forbidden from asking about dresses, I politely asked if I could ask her a few unrelated questions. She smiled sweetly. She would not be doing media interviews that night.

Before long, my Uber had turned back into a subway car and my leather clutch into a tote bag, and my feet began to ache. When I transferred trains at the Jay Street–MetroTech station, I wondered, “Did I just have a dream that I met Monica Lewinsky in the lobby of Saks Fifth Avenue?”

But when I looked down at my left sleeve, it was still stylishly missing.