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What to Wear on a Job Interview With Anna Wintour


Dressing for job interviews is its own special kind of hell. In the olden days, you just wore a suit and were done with it, but now there are all sorts of different interview uniforms and expectations. And that’s if you’re just interviewing at a regular job. Pity the poor folks who apply for jobs at Vogue and interview with the Devil in Prada herself, Miss Anna Wintour.

New York Magazine rounded up 13 of these brave souls, and asked them what they wore to meet with Nuclear Wintour, and whether or not they got the job. Haute couture seemed to impress almost always, but interestingly, there were a few folks who got gigs dressed in decidedly non-Vogue outfits. (Having parents who were teachers and living in Brooklyn seemed like a bigger problem, if you go by one applicant’s story.)

The whole list is fascinating, but here are a few of our favorites:

1. The Woman Who Spent $5000

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I have literally had cars that did not cost as much as this women’s interview outfits, which contained much Proenza, Prada, and Celine, and not a single bargain basement sticker.

2. The Woman Who Was Told Not to Cry

This is the lady who lived in Brooklyn and had the offensively employed parents. She wore vintage and borrowed a friend’s designer clutch, but to no avail. The hideous crime of living in an outer borough tanked her chances quicker than an Old Navy label.

3. The Woman Who Wore Doc Martens

“I didn’t know I was going to be interviewing with Anna that day, but even if I had known, I don’t think I would have chosen my outfit any differently … I just wore my favorite outfit from my post-college wardrobe: a dark gray Anna Sui pleated skirt, black cardigan, black tights, and Doc Martens. This was 1993, what can I say?”

You can say you’ll be friends with us and that it’s OK to bite your style for our next interview. Please, HR directors, make this the expected uniform for all interviews henceforth. High heels are so pinchy.


(Photo Credit: G.6sou/Flickr)

Jen Hubley Luckwaldt
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