Anna Wintour’s Former Assistants Reveal What The Devil Wears Prada Got Right (and Wrong)

25:08Okay. And the day before – the night before every internship, I would watch Devil Wears Prada. Oh, my God. Okay. Even though, like, none of the internships were that. But I never expected that I would be here, really. But I did not end up watching it before my interview with – at Vogue. I don't know why. It was a weird phone interview, that's why. Oh. You didn't go in person? To be in special events? Yeah, so I was in England when I got the phone interview. Yeah. Was that a beauty? No, it was with Kara Sanders, now Kara Brand. Oh, I love her. I still am indebted to her because she hired me off a phone call.

25:42Oh, that's interesting. But I met her over the phone, and then she was like, well, I'd love to meet you in person. And my dear mother got me a flight back to New York. And I met her two days later. I got the job that day, and I stayed for like three months. That's crazy. Sammy, did you read it? Right. No, and I still haven't. Oh, my God. I need to take a copy from your office. Well, I think you've missed your chance. Well, I need to ask someone else. I think there's like one left in the mini library in Chloe's office. So I will take that. But no, I had watched the movie only once, like a year before getting the interview.

26:15And then during the interview process, I watched, I think, half of it. What did you learn from watching it? Oh, gosh. I honestly learned more. The night before my interview, I watched Anna's master class that she has. Oh, yeah. And I feel like I took a lot from that. because there's a whole section in her masterclass that says how to prepare for an interview to be my assistant. So funny. But I think one of the things that stuck out to me from that is she just says she really wants someone to come into her office and be themselves. And so similarly to Marley, I have a background and interest in theater.

26:40And I knew that Anna did too. So that was a main focal point of our conversation was theater. What was your version of Sunday in the Park with George? What show had you just seen? Well, I was at CIA and we were repping a lot of clients who had shows that season that I knew Anna was seeing and interested in. I think we talked about Parade. That was the year of Parade. So Ben Platt, Michael Arden, people who are, you know, often around the Vogue world. And they were people who, you know, we were working on contracts for at CAA too. So, yeah. Interesting. People keep repeating to Andy in the film and in the book, a million women would kill for this job.

27:18How did people in your lives actually react when you got this job? So my friends from home, like, they didn't care because they're not in this world. I went to fashion school, so my friends from school were very excited. Did people ask you questions about the book or the movie? Yeah. The first question is, is it just like the book? Yeah. I mean, the movie. Is it just like the Devil Wears Pro? Yeah. Always. And I think the answer was kind of like, no. I mean, like— I say yes. I mean, I'm kind of like not— Yeah, like, there are shades, but, like, not like— Like, obviously, it's sort of a different thing.

27:53But, yeah, that is the question every time. But I think everyone gets that, whether you're in the office or not. Right? Yes, working at Vogue. Everyone gets that. Yes. Does she walk around with her sunglasses? Which also, like, not now. Yeah, not now, yeah. In the movie, there are two Emilies. There's almost always two assistants. There used to be three. When I started, Anna had three assistants. AW, one, two, three. When each of you started, usually someone starts as AW2 and then graduates into AW1. What are the difference between those two roles typically? In my day, it was personal and executive.

28:31And then first assistant was the executive. So you were really scheduling things, doing finances. Okay. What's the relationship between the two assistants? Is it mentor-mentee? Is it more peer-like? Does it depend? And when I was, it was very mentor-mentee. Okay. I felt like— It's not like Emily and Andy? I mean, I never had that experience. I was very much lucked out with both who was my first and then both who was my second. Who was your second? Carolina Gonzalez. She was great. And it was really nice to kind of, when you're going into a leadership role, have someone to kind of impart wisdom on, for lack of a better word.

29:06But I lucked out with both of my people. I think it was a really great experience all around. I obviously am very interested in events. And so I wanted to go to all the events with her and, like, manage all the events that she would go to. And also just, like, manage coordination with the events team as well. At a point, I really took whatever I wanted from the first. Because also, Jessie was very flexible. And she was like, if there's something that you want to work on, totally do it. And I would say for the most part, Anna funnels her communication through the first assistant. And as do most people in the office, too.

29:34And then the first assistant can decide what they want to delegate to the second assistant. Obviously, a big plot arc of the book and the movie is the sort of unraveling of Andy's personal life when she's in this intense job, which I think is not unique to this position. But I want to know how your personal lives fared when you were in Anna's office. I think everyone in my life at that time was very supportive of me. And I think everyone was kind of a conversation I had to have with the people in my life at the time of like, OK, if I take this job, this is what it will mean for my friends, for my family and every relationship I had at that time.

30:15And I think people are very excited for you. And they also like to hear about Vogue and hear about the world that you're in. So while your friends might not get to see you as much, I was very lucky in that. I had supportive people in my life who were able just to come over on the weekends and sit with me at home while I just sat on my computer. And you make it work. Well, first of all, I don't think I appreciate this at the time, but I think the fact that I was living at home the whole time. I was in Anna's office was probably helpful and kind of grounding. Like there were people at home when I got home no matter what time it was.

30:44And like probably – I'm sure being around my parents was sort of helpful in some way. But I'll also say that like, and I don't think this is unique to Vogue and like as you're saying, I don't think it's quite unique to like being in Anna's office. But like when you're working in media and the job is sort of like responding to things that are happening in the world, it's very easy for the job just to become your life. And I don't think that's like necessarily a bad thing. Like for me, I'm like Vogue people are my community. I think that's all just a function of like starting here when I was 22 and now being 31.

31:11So like I'm like these people are like the people in my life. I don't think of that as being a bad thing. I can imagine other people not, like, wanting kind of more of a separation between work and life. But, like, for me, they're just kind of knitted together. Like, that's just fine. Like, that's just kind of what it is. And, like, my Vogue friends are, like, my friends. And I think that's okay. Yeah, I agree. I lived with my parents when I first started as well. And then, like, halfway through, I think I moved out. It was nice. I mean, it was long hours. And sometimes my mother would just be like, what are you doing for that long that you can't answer my text messages?

31:43Oh, yeah. Was there anything? I found it quite striking in the book that Andy's roommate is trying to sign for an apartment with her and she feels she can't even say yes or no on the phone on a personal call. Yeah. What's the vibe in real life? I mean, reading that, I was like, why are you taking a personal call in the middle of the day? She was looking at the apartment. But I'm like, you're busy. And I was finding Lily so annoying. I was like, Lily, this is not a good time cam this way. Or Lily just signed the thing and figured out later. You know what I mean? I mean, I was like so anti-Andy and like throughout the book because I'm like, she's not taking this job seriously enough.

32:19She's not prioritizing this position. She has a bad attitude. No wonder she gets fired. Anyway, I mean, I didn't have any experiences like that. I was just kind of like, I think everyone knew not to bother me. If my parents didn't hear from me, they were like, she's working, you know. Yeah. Yeah. Yeah. It's really something you have to be OK when you sign up for. You know, you're committing 120 percent to it for X amount of time. And, again, that's why one of you said in the beginning, Anna doesn't have career assistants in part because of that mentorship component, but because you do have to dedicate so much, I think, of your time just to do a good job.

32:50And if you're going to do this, you want to do a good job. Yeah. Yeah, and you can't do it for long, so. Yeah. Well, speaking of which, what is a typical day in the life of Anna's assistants? Well, something I did find that was quite nice was like there had been so many assistants in that position that like it was pretty it was very organized and like very prescribed. I found like I had like a 21 page like handbook. It was nice to know that like so many people have filled these roles. So there are very specific ways of doing things, which I found quite helpful. Who updates the handbook? Is it like the outgoing first assistant when they leave?

33:24That's a good question, probably. I'm not sure that many things get updated. Like what changes? I know. But, yeah, the days start really early. Like someone's getting Anna coffee in the morning kind of thing or getting breakfast and setting up the office. What does setting up the office include? I know in the book there's like laboriously detailed going down to the newsstand, getting all the new newspapers and things, blah, blah, blah. That doesn't happen anymore. Everything she's reading early in the morning online, right? Yeah. For me, I think it was just setting up her breakfast and like opening her office doors.

33:56Yeah, it was like opening the doors, setting up the board, printing out the schedule. What's setting up the board? An iPad that we use on the desk where it shows her to-dos that day, reminders, and then who wants to speak with her. It's not printed. It's on an iPad. It's on an iPad because it changes so much. Yeah. So someone wants to see her. Because in the book, there's a whole thing about constantly reprinting. And it's who's fastest to reprint. Well, you have to reprint the schedule. And that changes often. Anna still prefers to see most documents printed. The board is probably the one thing that does live on a tech platform.

34:25But any emails that we help draft or send on her behalf, she has to review those printed. Even if it's a one-liner, she'll write and edit, and then it's printed. So any speeches, people are constantly giving things to her office to show Anna. And all these documents next to this iPad is something we call the inbox, and it's like a physical paper tray. And so throughout that day, we're constantly adding documents to this paper tray. and Anna will come back to her desk in between her many meetings. She's typically back to back all day. And when she has a few minutes, she'll just pick up whatever's in that physical inbox, write her edits, and then pass the documents back to her office to process them.

35:06And when she wasn't at the office, it was a lot of faxing things, learning how to fax things to her home. A lot of faxing. Yeah, so. I love that I felt so retro. Yeah, honestly. It was so interesting. In the film and in the book, there's a lot of when her driver calls up to say she's on her way up the security guard calls up she's coming gird your loins what's the real version of that? Honestly it's not as dramatic as that but it does happen you usually get a call from her driver saying that she dropped her off and it's usually two to three, five minutes depending on what time it is for her to get upstairs and you do want to be prepared But it's just like the people in her office like it's not the whole office It's just like her assistant.

35:49Well, by the time she comes in, there's no one usually there. Well, that's also true. She is the first one, aside from her assistants, in the office. But I do think that's not even just specific to Anna and Vogue. I think, you know, at a lot of companies where you do have a leader who has a lot of respect, and people feel that way when they come up to the office. But I mean, there's not this, like, mass panic of throwing off your flats and putting on your heels. I mean, I changed out of my clogs into more, like, appropriate shoes for sure. But that was like— What were your appropriate shoes, Marlene?

36:17I think I was wearing, like, smoking slippers or something. I was wearing, like, slippers. Okay. Because at first I was told that I needed to wear heels, and I was like, did for a bit. Who told you that? The first assistant, Corinne, she was kind of like everyone in Anna's office wears heels. And I was like, well, we're going to give that a go. And that really lasted for, like, two weeks. So hard. And then I was like, that is – because you're – you know, you have to – things are happening at a certain pace, and it sometimes involves a bit of running. Oh, yeah. And so I was finding it not practical to be in heels.

36:48Also, you're like running to print things. Explain why you're running. You just want to be timely. Yes. When she asks for someone, she wants that person very quickly. Yeah. You have to hurt people. Who are you hurting? Like any of the editors. Because people will slow down. And so if you walk like behind them, you can just. Oh, my God. But there is. But you don't want to. That's Shepard Taylor. I definitely did that a lot. Okay. So you would herd people to move them at a swift or pace. So basically, in my day, what you would do is the first assistant would call whoever it was, and then I would run to get them.

37:20Yes. And then sometimes the call would beat me or I would beat the call. And so then I would just hover until they were ready, which was if I hover, usually they are faster. And then I would let them walk in front of me and then I would walk behind them. Okay, yeah. I mean, I do remember a distinct when I started working here in 2011. It was like a flurry of fingers on the landline calling everyone's landline. So, like, you would get the second assistant, actually both assistants, and it would say, I want pre-release early and similar, or I want this run through early and similar to the book and the movie where it's like everyone's expecting it in an hour.

37:56Hands are flying to dial 14 four-digit extensions. And you get your, we all used to have landlines, RIP. You would answer. You didn't even have to hear anything. Like pre-release now. Pre-release now. Yeah. And then you'd have to run. And then after all those numbers were dialed, the stragglers would have to be gone and fetched and then herded into the room to keep things moving. Yes, exactly. But now there's no landline. So there's some cell phone calling. There's an email that will go out. But it's mostly running around. Yes. That's just tough. I mean, I think that's worse. I love the running around because you were so busy I could never exercise.

38:34You're also a runner. So I would just like run in the office. Wow, that was your exercise. Yeah. Like running down the corridors. Yes, I ran a marathon my two months. This November, I started working for Anna. That's crazy. A hard thing. One of the biggest moments in the book is about handling the book and in the movie. Can you guys break down what that process is actually like and what is the book? How is it used? When and where is it going? So I think back to what Anna's assistant's doing today, Her whole office is centered around something called the take-home bag. Take-home as in you take it home.

39:12And describe the take-home bag because it looms large. So it looms large. It's an LLB extra, extra large open boat tote. And this is Anna's homework bag. You know, she never wants anyone waiting on her for feedback. So throughout the day, it's Anna's assistant's job to think about what she needs to review that night in order to be caught up. So they're printing out different documents, whether it's speeches or event guest lists. A copy from the magazine. Yes, that she needs to include. That's a big one and something I'm really impressed by is that Anna reads every single thing that goes into the magazine and that all goes into her take home.

39:45And she will read if three 4 ,000-word pieces come in in one night, she is giving feedback, very detailed feedback on all of them by the next morning. Exactly. And the bag is that process that allows her to do that. And so the book is just another one of those items that goes in the bag. And this is a dummy book of that magazine issue that's coming out usually three months later. We start these, you know, I'd say three, four months in advance. Well, for example, right now we have the book of the summer issue. And that will come out in early June. And it's a printing, eight and a half by 11 printouts of every page in the magazine in a three ring book.

40:25And she's going through and a lot of post-its are going on that book. So how long do you have to wait to get the book to take it home? Sometimes it was late. Yeah, it really depends. I would like to say Anna has a doctor's handwriting. I was going to say, are we allowed to talk about that? She's talked about it. She's talked about that. The village it takes to decode. It's so sensitive. They're better. I used to send them photos all the time. When Marley cracks something, I am in awe. I still, there was one time when I couldn't, it was something that Taylor Antrim had and I could not figure it out.

40:57and I got it at like 10 p.m. that night because I could not stop thinking about it. Oh, I don't remember now. It's the best feeling when you got something. When you resolve it, it's amazing. Sometimes I find you have to take a picture of it and really sit with it for a while. Yeah. You would like flip it upside down. Yeah. There's a lot of context. And like hover over things. Literally. Yeah. All this to avoid asking her. Well, I would allow myself to ask her once a week. Oh, I was asking her like, I was like, there's no time for this. I was like, and sometimes, and I'll be like, oh, I don't know.

41:27Like, she would sometimes say, well, how would you just have to, like, take an educated guess and just see if it's right? Yeah, exactly. For remarks, I would always be just like, well, this works. Yeah, you just have to give it a go, and then she'll tell you if it's wrong. Oh, exactly. She'll always tell you if it's wrong. Yes. Okay, in the book and the movie, run-throughs loom large because it's quite—I feel like people are so fascinated by those because they're so physical. It's like moving racks quickly down a hall into her office. Are the assistants involved in the run-throughs at all? What does that look like?

41:57We're involved in scheduling them. Okay. And then sometimes we help with a rack, but mostly not. Yeah, moving the racks around, I guess. It was fun to listen, though, because that's one of the things that really is true to the movie. Yeah. And I remember that was a cool moment where I was like, wow. I'm on Vogue, and it's, you know, because you get some of the things. Like, give an example. Like, what are some things discussed? They discuss, it's really that whole cerulean moment. You know, they roll a whole fashion rack or two racks into Anna's office. Trades of accessories. And it's the sittings editor and our global head of fashion, Virginia Smith.

42:29And they run Anna through all the clothes that they have picked out for whatever upcoming shoot we have. And Anna gives her feedback. And the feedback might be, this looks great. It might be like, it mostly looks great except for this one thing. Or it might be like, we need to totally start over. And they were talking about the casting sometimes. Yeah, so talent is usually there. Raul is always there. I remember when I was first, it was always trying to figure out where Raul was. Because he's so busy, you know, he's always running around. Do you do run-throughs? Yes, I do run-throughs. Anna also now often will come down to the closet now that it's on 20.

43:03She still likes to be involved in a run-through. I think she really enjoys it. We've been doing them together, or I'll just do it alone with Virginia and Naomi and the sittings editor. I also think it's nice to have the photographer involved sometimes. I think that they that will yield some feedback that you maybe didn't expect. But I find run throughs are really helpful. And I think before I was in this current role, I didn't appreciate what a difference they make for really grasping this sittings editor's vision for the shoot. And that can really make a difference. All right. We'll be right back with Anna's Angels.

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44:44So obviously in the movie, Andy undergoes a major makeover, but can you guys debunk that a bit? Did any of you go through a makeover? Do you get dressed from the closet? Can you discuss what an assistant's dress code typically looks like? Are you wearing heels like Marley Marys? I wore heels every day. Really? I wore Joseph boots with long black trousers and then just a different sweater every day. Interesting. How high a heel? Three inches. Okay. Good for you. Oh, yeah, but they were the most comfortable. I mean, I wore them to my first met. It was, they were the best. I've retired them, though.

45:20But you did, like, kind of have a uniform. Yes, definitely. Wore black trousers and a shirt, sweater every day. You still sort of wear that. Yeah. Because I was, like, since I was, like, such a sort of Vogue fangirl, I, like, really— Glad you said it. I know. But I really, like, admired Tawny Goodman in particular. And I was, like, okay, it's cool to have a uniform. Like if you like look, you know, you can kind of wear the same thing every day if it's like very neat. And so I would wear like a white linen shirt, like collarless linen shirt and like black pants and then like smoking slippers or whatever and like maybe a sweater.

45:54And I did that every day because I was like I don't want you don't have to you don't want to have to wake up and like think about what you're wearing every day when you have to wake up so early. There were so many assistants like Jesse would have a full outfit every day. But so did Jasmine. I just didn't understand how they did that. I know. I mean, because I was also like, I'm not a fashion girl in that way. Like, I liked fashion a lot and I appreciated it. But, like, I wasn't, like, getting, you know, being dressed up wasn't quite my thing. There was a woman I, and I was getting interviewed by someone in the office and I had to greet them.

46:24And they wrote about me in the interview saying, and the assistant was wearing all black. Anna must have hated that. Oh, stop. I was like, she doesn't care. Sammy, what's your uniform? I'd say I'm usually in some sort of a heeled shoe. My first two weeks, I did wear like a full like pump and I had crazy blisters. Like couldn't, it was so bad. So I retired that after two weeks after seeing how much we had to run. But now I'll just wear a booty usually. I prefer some height. If we come in on a Friday, that's when I would use a ballet flat if my feet were getting tired. But yeah, I'll just wear like black pants and usually a blazer.

46:58I feel like you do a big suiting look. Yes. Yes, I feel like dress for I like the phrase like dress for your day. But I also think when you're in Anna's office or any role at Vogue, you never know what's going to happen. And so, you know, you have these like important meetings with important people pop up. And, you know, last week, you know, it was a Friday and I typically dress down for a Friday. And then, you know, Anna has people meeting her and she'll pull you into meetings. So it's always, I think, nice to have at least a little blazer. Dress for the day you want. Dress for the day you want.

47:26I like that. Yeah, but that is what I try to do. when the, like, what's the worst Anna's ever seen you in? I want to debunk the closet. Yeah, you don't. Because there's no borrowing from the closet. No. Like, I remember when I started Vogue and I was covering a lot of events when I was in my 20s. I, there was a certain rack of the closet where you could borrow shoes. But, like, the Manolos were kept in a cupboard locked by key. And only Mimosa had the key. Mimosa is the keeper of the Manolos. The keeper of the Manolos and everything else in the closet. But there's not clothes to be borrowed in the closet because the closet is really clothes that are called in for specific shoots.

48:07There are, say, undergarments that are kept, tights, hats, things that you might need to accessorize or help a shoot. But clothes themselves, it's very rare that that's happening. I will say, though, like for the Met, you can, I mean, I have borrowed shoes for the Met, I think. Yeah. I mean, I feel like on very special occasions, if you're really in a pinch, you can probably borrow something. But you're not – clothes aren't being thrown at you for, like, events. But you can call them in, which is lovely. Sure. Some people can borrow clothes, but that's a favor that fashion PRs do for Vogue. It has to be meted out with a care.

48:47Yeah, totally. But, yeah, it's not the way it's described at all in the book. I will say people dress very differently now than when I started, where it really was the opening montage of the film of, you know, women having five almonds and pulling their stockings up in the perfect shoe that's four inches high. And no one was wearing those shoes on the subway was kind of the vibe people wanted to give off. And now I feel like everyone's walking around in Adidas by Wales Bonner and Roll Neck J.Crew. Yeah. I'd say there's like the one unspoken rule. I think it was never explicitly said, but in Anna's office, is that there's no jeans or no sneakers.

49:28So you have definitely no jeans. Yeah. But other people in the office will wear those things. Yeah. So when I graduated out of Anna's office, it's the first thing I did. I started wearing jeans to the office. It was amazing. Wow. Marley, I've never seen you in jeans. I don't really like jeans. I don't really like a jean. God knows I dress casually in other ways. But, yeah, not really a blue jeans kind of gal. Did anyone ever give you a makeover of sorts or take you under their wing? No, no. No, but I do remember, like, again, the one event that I went to in Anna's office. Like, I do remember, like, Tawny kind of, like, helping me with, like, I was wearing, like, this, like, long red dress from The Row.

50:10And I feel like there might be some kind of— I know, but I feel like there was some kind of, like— I don't know whether she added this ribbon or, like, it was, like, closed by a ribbon. And I do remember her kind of like doing something. And I was like, oh, my God. I was like, this is crazy. So that was the – and then also, you know, people are helping with Met stuff. That's kind of the example. The Met, I would say, Willa Lindley has always been the person that helped me. Annie Choi also would help with like staff. Like not – yeah. I want to know what it was like working your first Met. I mean – Any fun stories?

50:40Long day. Did you have to memorize a face sheet and whisper to Anna when the ambassador and his new mistress arrived? No, that's my job now. That's Sasha's job. She does a great job at it. Thank you. I unfortunately know everybody. But they don't know me.

50:56I didn't have to memorize things. I think my biggest, the weirdest thing was running up the stairs. Like running up the red carpet stairs. That was unnerving because there was just like so many cameras and so many people. And you think that like eyes are going to be on you when you're running up those stairs. But no one cares, which is fantastic. but I got caught on the live stream and woke up to many, many texts being like, I saw you. Oh, that's funny. When Anna arrives to the Met, she does all of her press interviews and then her assistants arrive with her but they're obviously not doing the interviews with her so we kind of just make a beeline behind her up the stairs and then wait for her at the top.

51:30All right, anything else from the film or book that you would like to debunk or the biggest misconception about being Anna's assistant? Well, I mean, an important point that's made early on and then you sort of see it at the end is really how supportive Anna is when you are moving on. And I mean, all three of us are good examples of this where, I mean, certainly most of the moves that I've made through Vogue, Anna was directly responsible for. Like, she moved me out of her office into working with Mark Colgate and Hamish Bowles. And then in 2020, She got on a Zoom with me and she was like, your assisting days are over and now you're working on the culture team.

52:13I think she was the one who suggested that I write the Zendaya cover story. Like when she feels that you've done a good job or when she feels like you've been in a certain role long enough, in my personal experience, she's very supportive about helping you make your next step. I think she wants people at Vogue to sort of feel fulfilled and do jobs that are appropriate to them and, you know, not sort of feel stagnant. and she, I think, believes in people before maybe they necessarily know what they can do. And that, yeah, I mean, I'm sort of very grateful for her for that reason and for lots of reasons, but certainly for that reason.

52:47I mean, Sasha's planning the Met Gala now. Literally. To go from Finch at the airport. Honestly. Honestly, the glow up. Feels just like yesterday. Yeah, I know. Finch up. Okay. Thank you, ladies. Very exciting. Thank you. Surreal Emily's.

53:08All right, that's it for the show. See you next week.

53:14The Run Through with Vogue is produced by Chelsea Daniel, Alex DePalma, and Alex John Burns with help from Emily Elias. The show is engineered by Bran Bandi and mixed by Mike Kutchman. Bye.

53:35From PRX.