The only thing that’s more intimidating than a meeting with Anna Wintour is a job interview with her. Even among staff members whom she likes working with, the editor-in-chief of Vogue is notorious for giving employees’ outfits a knowing once-over. So what happens when you not only need to dress up, but also must choose a look that convinces her you’re Vogue material? That’s what New York Magazine, The Cut, asked dozens of people who’ve been through the ringer in the past few decades. Here are some of our favorites:
1. The Woman Who Spent More Than $5,000.
They surprised me with scheduling my interview the very next day. Not having worked in fashion, I didn’t have anything nicer than J.Crew. So, after work, I went to Barneys because it was the only store open until eight and I could bang it out. I also found a nail salon nearby open until nine, and got a blowout the next morning. I bought a silk Proenza tank dress, Prada heels, and a Celine belt. It was like a supermarket sweep, and I spent about $2,000. I didn’t have a new bag, but then the receptionist held my (now downmarket) Marc by Marc bag anyway. They made me come in for another interview, which threw me. I started to really get into it and money stopped becoming a problem. I got a shift dress at Prada from the spring collection and then they sold me the blue patent shoes, and it all looked so good. The dress needed tailoring, but it was going to take a week and I needed it in a couple of days, so I name-dropped and they did it fast. The dress actually was on sale but still more than I ever paid for everything. I think that purchase must have been $3,500.
Got the job.
2. The Woman Who Was Told Not to Cry
I didn’t spend much money at all, as I have a stash of vintage finds. I wore a vintage, linen apricot dress with gold buttons and gold peep-toe heels. I borrowed my friend’s Prada clutch to match, and wore some jewelry from David Yurman, where my friend is a designer. Before the interview, the managing editor asked if I’d ever cried on a job (I hadn’t), because she and Anna “hated going into bathroom and fashion closets and hearing girls sniffle and cry over the ‘little things’ that go on throughout the day.”
When Anna opened my portfolio and saw my address, she said, “Ah, okay. So you live in BROOK-lyn, huh?” She seemed put off by that, and also asked what my parents did for a living. When I said that they used to be teachers, she was not impressed.
3. The Woman Who Bought $1,000 Shoes
I got a call about my interview in the evening around 5 p.m. on a Monday night. “Can you meet with Anna tomorrow at two?” I agreed, hung up the phone, and ran to my closet. Nothing. I called a stylist friend, freaking out, who said, “Calm down, she is a professional, she interviews people all the time. Stop making such a big deal about it,” before adding, “but whatever you do, don’t wear last season’s anything.” I had time to go to Soho for a pair of shoes and was waiting outside when Kirna Zabete opened. Somehow I decided that my best option was a pair of Proenza open-toed, stacked heels, despite the rain. I justified the $1K price tag and ran back home to get dressed. I paired them with 3.1 Philip Lim high-waisted, silk pants and a black Celine tote I borrowed from my stylist friend, with a belted coat by Apiece Apart. Everything else I kept super simple: little to no makeup, straight brushed hair, and a wedding ring. By God, no fragrance.
Got the job.
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