Hi everyone, I'm Rachel Zoe and you're listening to Climbing in Heels for your weekly dose of glamour, inspiration and of course fun. My styling career really really caught fire in the late nineties and early two thousands, and I at the time was working in the music industry. In fact, I was eating, sleeping, and breathing in the music industry. I worked with a lot of everyone's favorites. So it's
very exciting and lots to discuss. So here to help me dive into some of my more famous Y two K is my producer Mary Elizabeth, So let's get right into it. How exciting.
As Rachel mentioned, for some reason since January, you have been getting a lot of requests for quotes or stories or trending topics about your experience in your Y two K styling era. So, as you mentioned, you started in the music industry in the days when music videos were the biggest marketing tool for a label and a song. So the days of TRL which I was obsessed with, the butterfly hair clips, the capri pants, the layering of
the tank tops. The Y two K fashion is back, whether we like it or not, and I think before. So I put up in your story for our listeners to answer questions or ask you questions that you will answer about Y two K specifically, and it, by far and away got more responses than maybe any sticker I've put on your story like ever. So we're going to jump into listener questions that they have about Y two
K and your contributions to the era. But I thought it would be fun first to lay the scene for everybody.
Also, I want a sidebar. You said late nineties or I said late nineties, I wasn't. I mean I was like a kid then? Oh sure, for sure? Oh yeah, yeah, a kid she was to do anything in the night.
Definitely, not a full adult, definitely not. Yes, I must have been wrong on that. So I thought it would be fun to first lay the scene for listeners about the iconic music videos that you worked on, because all the millennials like me who know and love you from the Rachel Zoe Project grew up in that era of like I said, TRL and waited on baited breath for our favorite pop stars to drop their music videos, and you were a part of some truly truly iconic ones that I don't know if everybody.
Knows, well, I'll be honest with you, I don't know all of them, because I will be very honest with you my life from the minute I went freelance, I legitimately it's like I always say to you on the regular,
like it's a blur, actual blurb. Because the music industry was on such fire, and the amount of money being spent on every aspect of the artists their life and all that was so intense, and like the speed at which these pop stars were working, shooting, touring, performing I and I was like me myself, and I was like, yeah, one assistant with like fifty racks of clothes. So I like, when you say it, I'll be like, oh my god, of course they did that. But like if you asked me,
I could remember probably like a handful of them. And like when I hear a song now, like of Backstreet Enrique or Jessica Simpson or Brittany, I'll be like, oh I did that, You're like, oh, crap, I was on set. I was actually on so okay, I did that? Look right, I love it, Okay, so let's kick it off.
I mean, the Y two K Queen was definitely Miss Britney Spears yes, and you did work with Britney Spears. I did, And you did work on correct me if I'm wrong, hit me baby one more time.
I did. So that was actually one of my very first freelance jobs because there was a woman. There is a woman out in the world. I haven't spoken to her in forever, but Hailey Hill, who was my boss at YM magazine. And Haley was the senior fashion editor fashion director at the time, and she would get booked on these big commercials and stuff, and she was booked on Britney's video and stuff through Okay, her manager, Sonya
Muckel Okay, and Sonya who I remember, like yesterday. I think I ran into her in the last couple of years. It was wild and Haley needed help and she had two jobs booked at the same time. Its like one of those things. So I was still working at the magazine and I think it was being shot on a weekend, okay. And do you remember where it was being shot? No, Like I want to see Brooklyn Queens, Like I can't, you know, like at a stage or studio. I can't remember,
but that's for some reason feeling familiar. And she called me because she needed help and so I went in and started just working on it and like pulling the clothes and doing the prep and like being on set and whatever. And I think at the time, like I was so obsessed with being great at my job that I never looked at stars as stars, if that makes sense. Yeah. I don't think in the moment I knew or cared
that much that it was Brittany. I knew, but it was more like I was such a fashion girl that to me, like if you were, like you're going on set with Carlagerfeld and Kate Moss, that would have given me a cold sweat panic attack. Sure, you know what I mean. And so I think just.
It worked in your favor that you weren't a fact starship or just obsessed with exactly music it served it served you well.
Yeah, I was able to, I think, maintain professionalism without like freaking out because I was so young. Yeah you know what I mean. I was so young, but yeah, I felt so much older than these I mean kids, they were really some of them were, you know, like Kevin Richardson was not a kid, right, Okay.
So that leads me to the next group, which is the Backstreet Boy.
But the Brittany. I want to touch on one seck because after I did these few jobs working with Haley, that is when that was the impetus for me going freelance, really because I made so much money on those jobs that I was like, what the hell am I doing? This is creative, this is fun, Like I'm out in the world. I'm not sitting in a fluorescent lit office,
you know, I'm not locked in a fashion closet. And so this was sort of like I just felt alive, honestly, And that is when I made the movie to go freelance, like shortly after that, because then I got promoted and then I and then I went freelance probably later that year, left there as senior fashion editor. But it's important because as senior fashion editor, I was styling a lot of
shoots for the magazine and all the covers. Sure, and I met a lot of publicists and a lot of pop stars and actors, Like that's when I met Gwen Stefani, how she got on cover shoots Drew Barry. But that's really how you got your foot into this, like music, That's how I met the publicist love that later helped would hire you to hire me so I made a lot of connections there, and then after I was working with Brittany, I worked with Brittany on my own a bunch.
I flew to the World Music Awards to Monaco for twenty four hours. I thought I was never going to work again, because I got there. I flew with her and the bodyguards and like the team, and I just remember like I had like no notice. It was sort of like you're leaving tomorrow and she she has to be out World Music Awards and Monica and you're going.
And I was so again, I was so young, so it was like, okay, you know, I just never unpacked a suitcase and like blah blah blah, and I went and I remember getting there and I remember that the managing team going, okay, everybody break, take a nap, take a shower, whatever, And you know, me, Mary like, I don't nap, I don't sleep. But what did I do? I fucking blacked out. I blacked out. And the next thing I remember is security banging on my door telling me we had to leave. She was going on stage.
I had to get her ready. I'm by myself. I had no assistant, like I was literally that was like one of the most panicing for you in my life.
I can't even imagine it, but for you to fall asleep that hardcore because I know you sleep like because it lighted all night, worst sleeper maybe in the history of the world, you must have been like truly exhausted.
But that is that is really and it was terrifying. I was like, she's going to miss her performance or go on naked because I fell asleep, and I'll never work again. And by the way, that was truly the feeling and psychology that I had, probably for the rest of my career was the was the like, if you fuck this up, you're you're not working anymore.
Yeah, that's it, You're just so you're working with Brittany. How was Brittany then? Was she?
You know, she was great? This is the sort of the beginning of her mega success. She was great, and I think she was great. She was cute, she was bubbly, she was fun. Was she collaborative with you? Did she like getting dressed? Or was she stubborn? Uh? It was more. What I very clearly remember was that I was trying to I think make her a little uh, sort of
create a more what do I say fashion. I guess maybe less sort of ripped everything, yeah, whatever, And I was trying to do a little more fashion than I remember, a little more polish. And I remember she was per forming share song at the World Music Awards. You know what's it? An? A rhythm to oh lad daddity mmm mm hmm. Yeah, I remember the name of the song. When the beat goes on, Oh my god, thank you.
My brain hurts from thinking about that. And she was incredible, and she had like long hair, and I was like, Okay, I'm going to give her this like very share like kind of try to do this like Bob Mackie, like, you know, just a very like whatever. And I just remember it was this long, like I believe, if I remember correctly from five hundred years ago, Donna Karen like did this like custom like cature at that time, because we used to do all these awards show dressing looks together,
like we would do custom things for clients. But she was doing this very special. It was like this long beaded like almost like a mermaid fishtail long skirt, and and basically we put this top on her and I just remember like two minutes before, two minutes before she went on stage. She went in the bathroom and cut it. She cut the guitar, She cut the guitar, She cropped the top to just below her boobs. If I remember correctly, I cried yikes. Yeah, I mean as the stylist. I'm sure you cried.
Well.
I cried only because I was like, am I fired from Donna Karen?
Now?
For life? Have I ruined my reputation? Yeah? Did she hate what I styled? But she looked incredible, she performed great. We all went to this big dinner with Prince Albert, my god, and at that that was the beginning of my very surreal life. Yeah. Really, and that's twenty years. Jumped you to Backstreet Boys, which yes, same same management. It was with the Firm, a place called the Firm, which had Enrique Backstreet and Brittany and I want to say in sync, but maybe that's wrong.
That wrong. For millennial girls like me, you were either Backsheater and sink and there was no Well, it's.
Like are you Edward or are you Jacob? Of course yeah yeah. And now with summary term pretty, it's are you Conrad or are you Jeremy.
I mean, it's just it goes on forever. Doesn't it Backstreet Boys equal to basically Beatlemania beyond in terms of like beyond the logistics of them traveling touring being right, it must have been so insane to not only have one very famous client, but five very famous I.
Can't really explain what was happening.
Now. You didn't do correct me if I'm wrong. You didn't do the Backstreets back music video, right, the one where they're like Phantom of the Opera and it's like the dance like the Thriller vibes where they're That.
Might be right when I started, because you started with the Millennium album. Was that my first? Or was that my last? Into Millennial that I literally cannot remember? You can't remember. I have to watch that video, okay, but I very very remember.
Very like Michael Jackson Thriller inspired, they're like dancing, it's like sort of a haunted mansion vibe.
What do I feel like? What were they wearing? I could tell by what they were wearing, Like, did they look like I styled them?
No? Because it was so theatrical, right, so like AJ has like the Phantom of the Opera mask on it, right point, like Brian, I think it was Brian is like a werewolf man. Like.
It was very, very theatrical. I did so many music videos with them, and we did think, like there's nothing we didn't do, so it's possible. But I remember Millennium because that's the all white else. Oh well, yeah, I remember that like it was because I remember walking into my hotel room. I had been prepping for so long. And what you have to remember and I need people to try and like visualize what my life was with Backstreet. Imagine five kids different like anyone who has five kids.
You could have ten kids and not one of them would be like sure, not one of them would dress the same, not one, right, And that's what it was like. And it was like five guys that I loved honestly deeply. I was so close with them. They were like brothers. And Kevin was like a friend because I think we were the same age. Kevin was the light, the other one yeah group Yeah, and Kevin kind of felt like, honestly like the dad of the group, you know, and
he and I hung out. I loved his girlfriend wife, Kristen, and you know, I went through so much with all of them. I would say Nick was the baby and really felt like the baby, you know, and I genuinely think I just remember white ray black, but like Millennium obviously was all white. But I remember ideating with that, and I remember saying like, it's a new century, it's a new like everything should be clean, everything should be new.
And I remember like creating that and saying like, they need to look modern, they need to look cool, they need to clean, they need to like look cohesive. And that was the biggest thing that I focused on with them, was cohesion, because I felt everyone needed to have their own style and their own take on the concept, which they did, sure, and that was the challenge, right, But like we would have if it was five guys. I swear to god, I had a minimum of five racks
per guy. Yeah, so I would stand there with, you know, fifty racks of clothes and white, overwhelmed white, white, Doulce white, Gucci white, yeah, you name it, white, Zara white, everything white, everything right, Calvin white. You know that's insane. Yeah, it was. It was overwhelming, that's insane. My wardrobe budgets were And remember in those days, it was not like computer based. We didn't have like the cell phone world like it
wasn't like that. So there was like Star tax phone, so we were not I was not doing expenses on a phone. I wasn't taking notes. Everything was paper, everything was taxis, everything was food, paper, receipts, everything. So if I had like one hundred thousand dollars wardrobe budget, two hundred thousand dollars wards budget, I had to account for every penny of that. And the worst part is a stylist, as any stylist will tell you, is you have to lay out that money and then you wait and you
wait to get reimbursed. Oh, it's a terrible model. That's terrible. It's a terrible business model. Literally, it's a terrible business model. So every bit of my free time that I didn't have was spent taping or glu sticking, TAXI receipts, food receipts, tailoring alterations, shipping, purchasing. You know, I had to purchase a lot of stuff. I had a lot of stuff
custom made. I would be like down on a street getting random like things for a j like feather things, or like I would I would get like embroidered or studded, Like I would buy a leather vest and have someone in a street, just like add studs to it, or grammets on the shoes or denim rip it up. I would tie things to like a car and drive so they would get beaten down. I would wash them. I would just try and.
Like wear things down T shirts. I would teasting. Remember the Hi die.
You name it? Oh my god, I need the job. It's too great. Yeah, Okay.
One of my personal favorite music videos that I'm obsessed with you working on is mister Enrique Glecia's Hero.
Oh my God, that song, that video.
I would wait for TRL because I thought he was so gorgeous, and I also like the drama of the song in that music video with like Jennifer Love Hewitt and Mickey.
Rourke with no idea.
I was obsessed with that that.
Is video and that song. That experience was perhaps one of the craziest experiences of my styling career of my life. Yeah, I will remember that video forever for many reasons. That and another Enrique video where he met Anna wife that is so funny. And another Enrique video where I styled him with Whitney Houston. Oh and that was unforgettable.
I want.
And her daughter came to set. But Hero was a stressful job. So hero was crazy because it was this director, Joseph Kahn, who at the time was the yes, the guy. I worked mainly with Joseph Kahan. I worked with Francis Lawrence a lot. He did a lot of the video so now directs like very major emotions. Yeah. That video was in Palm Springs at the MERV Griffin Estate. Okay, if I remember correctly, we stayed at you know, one of those great hotels. I remember getting there like two
in the morning. We had to be on set at four thirty. A prop stylist actually died on their way to set. It was the absolute saddest thing because she drove off the ledge. There was no railing on the location we were going to we were shooting, if I remember correctly, like August twenty seventh or August twenty something like that desert in the middle of the desert. It was just one hundred and four by seven am. Oh
my god, Alia died. Alia died. You got the news that we got the news that she died while we were on set in the desert, because she was also shooting a music video in the Caribbean. Rage yep, yeah, pay cash and so it was all these weird, weird energy. Yeah, Mickey work was there. I was in a hotel hotel with Mickey York and that was wild wild he by the way, he couldn't have been sweeter to me. For
the rocker and Jennifer love Hewittt. I had known because we had done a bunch of shoots together, because I think she had done like Party of Five. I had met her through like y Am and then I and then I became her stylist for a bunch of things, and so I was doing her and Enrique, and you know, Enrique is one of the most professional people you've ever known. He he just is and he would show up. He is by far and away the most handsome and charming.
Love that person. Everything you want Enrique to be. He and Moore and me styling. Loves to hear that me styling Enrique as much as I would try and make him a little fancier at times jeans yep, vintage Levi's like vintage jeans hoodie type. I got him to go sometimes from a baseball hat to a beanie, which ended up being like a signature. So that was a moment
I loved him. I still love him. I always love him, and I styled him for the video where he met his wife Anna Kornakova, and I styled her as well. And I remember so clearly standing behind the monitor because I was obsessive about obviously everything and like I looks close everything. But I had the thing with me beyond styling. I would always I really did everything in terms of like I watched the lighting, I watched the angles. I would suggest to the directors how it might work better. Yeah,
I would sit in all the time. I would try, you know, like I was so in it. You were very present every part of it. But I remember standing behind the monitor and I remember looking at the director and looking at Enrique's team, this guy Fernando at the time, and I was like, I was just pretty real in this one. This may go passing video.
Everyone might be going on and they've been married for a long time and together ever since that. Oh I love that so much. Okay, rounding out your iconic music video moments, we have to talk about Jessica Simpson. Okay, we have to talk about these boots were made for walking. I mean, you fully dressed her like Daisy Duke, right, she had because that the song was for promotional for the movie.
That was amazing.
I just had it with long extensions in Yeah, Ken Pavis is the tiniest denim shorts you've ever seen ever, ever and like a midriff tank.
Top she looks, and a big belt belt right, that belt needs to understand, because I think it's so important. If you don't know what stylists do, what I need to explain to you is that when you look at that video of Jessica Simpson and you look at okay, she's wearing these cowboy boots, a big belt, these little denim shorts and this crop top. Okay, great, and I think we did cool earrings if I remember correctly. She's
so good in that video, honestly. Yeah. But what nobody knows is that to get to that look, there was literally fifty belts laid out with different buckles and different straps. There was maybe thirty pairs of cutoff denim shorts, maybe more. To make sure they were the right fit. We would have tailors on set that would make them shorter. To make them shorter, then free them so they look vintage cowboy boots. I mean one hundred pairs, oh my god,
and like the t shirts. I mean, you know, I would run up and down Melrose and Librea and go all the thrift stores. And you know, it's not what it looks like. That's all I'm saying. Well, the simplicity of.
You know, denim shorts and a tanked up and whatever, I think to an outsider goes, oh, that's so easy.
Anyone could do that now.
But the amount of a approvals it takes to get to the final outfit and.
Getting the final outfit and then keeping it.
You know, you're shooting these music videos for more than one day, most likely keeping them looking good, having multiples to put on if she rips it or drops whatever on it or whatever. It's it's more than just a pair of shorts and a tank top.
Oh yeah, it's it always is always, it's always. Oh key dokey.
I'm gonna go rapid fire right into our listener Y two K questions. Okay, this covers a lot of different sort of like Y two K E topics, but let's do it.
Let's do a rapid fire. Okay, okay, Question one, who is the nicest star from that era that you dressed? I gotta tell you, I mean, you know, the Backstreet Boys, like I said, were literally it was like it was like almost like I was their sister. Yeah, slash mom, you know that always was with them. Enrique, he's an angel. He's an angel. You we're so close, Like I love that.
You're too nice to know it's true. I would honestly tell you because anyone that was a nightmare, like I didn't have time for honestly, yeah, you know to do it. It was nice. And Jessica and I were like related literally yeah, like I was part of the Simpson family at one point. Oh my god, I love that.
Okay, who do you wish you could have styled from that era? But never got to? I think you could do like music or otherwise. I mean maybe j Lo Jalen right, because.
That was like her Jenny from the block. Yeah, you know you know who else I feel like.
And I don't even know if you have worked with her, but like talking about like more nineties whatever, But Alicia Silverstone, I did share horoit.
I work with her.
I styled for different shoes, Harrow Smith's music, right, those music videos. Yeah, but I feel like she and I feel like she could have been like a client of yours.
Like no brainer, just with her like aesthetic.
Okay, what accessories from Y two K stand out to you the most? Like when you think about just accessories and having to like have a thousand options of blank, what is it?
God, I'll be honest with you, Like I should remember coats, coats, like jackets and like and like accessories, I mean hats. Yeah, there was a lot of hats.
I feel also with jackets. Y two K had an interesting big fabric.
Yeah, it was that techie. It was the that's why I keep going like scuba gears. It was neoprene. Yes, it was a lot of neoprene, a lot. But the thing with me, though, truthfully, I think I'd never succumbed to the oversized cargo pant and the like the sneakers with the big socks and stuff. And I think that's why in its resurgence, I'm like, no, see, I didn't. I didn't like it. The I was trying to go
against the crop top, you know what I mean. So I think for me, I was shifting into like the nineties, like this sort of minimalism and the chic and then the sort of like over the top, and I you know, I was just about pretty. Yeah, but for guys, to be honest, my vibe was like just look hot, yeah, Like and to me hot was Brad Pitt and thelm
and Luise Like yeah. To me, it was always trying to make the guys, especially with like Enrique, it was that like, no, like look like Johnny Depp with Kate Moss, like beat up jeans, cool belt, beat up like Chelsea boots. Yeah, and and like a cool like leathers or swede jacket with a vintage tea Like to me, that was cool. Yeah. And that's where I was trying to take the guys because that's where all of like young Hollywood, that was the young Hollywood vibe. Yeah, And so I was I
was able to do that with Enrique. Yeah, you know.
Okay, we got this question a couple of times. Oh my god, why did thongs become popular?
And hy two k oh my god. It was like a thong. It was like a thong craze.
I mean, there was even the song Paris Hilton.
You know, I don't think we've talked about Paris Hilton here, yeah, like Nicole and everything, because we're talking about music, But I mean I think Paris was like Juicy Sweats, which was the biggest y two K fashion. That's a thing,
like I can't we can't forget that. That was Jalo Madonna and like the whole velvet track suit of like my friend Pam Levy and Gila that created the Juicy track suit and that was like rhinestone like bedazzled track suits, be dazzled jackets, kits in you know, the bedazzled everything. So I think we can't like not mention that because I think you're a part of Christina Aguile like all of them. And Christina was opening for Backstreet Boys at the time.
Oh my gosh, that's so crazy because she obviously went on to be her own.
Massive success story.
Yep.
So yeah, the thongs like coming out of the pants with black hairs, and then we did the the low sung jeans.
It's almost like the thong craze happened because the jeans were just too low.
Yes, it was god awfully low. And just to be clear, I want to be clear, I was not an advocate for that, sure, sure, you know, I mean I think Paris, like I have such a clear visual of when I met her with like the cropped bleached white platinum hair in like a pink velvet sweatsuit with like so low but she looked so hot, you know. Yeah, and she was so sweet and friendly. Honestly, yeah, but kits In. I just keep thinking about kits In. Oh yeah, it was the craze. Okay, next up then eyebrows. Just why
just why is this? I tell you why? Because that started because of like Calvin Klein, John Galliano, all the nineties, Supers, Kate Moss, they all did it. It would tweet their eyebrows off. It was part of the minimal the you know, the minimalism movement, and it was all the nineties with Matt Brown makeup, you know, very neutral palette, Matt Matt lips, thin thin eyebrows, very wafy movement, yep, and very minimal no bells and whistles, no jewels, very clean. It was
the Kate Moss Calvin movement. Honestly. Yeah. And Kate Moss, like I mean she was like sixteen, I know, I mean she she changed the whole.
I mean, some of us millennial girls are paying for the overtweezing to that.
I would like to proudly say that my mother. I have to thank my mom for not letting me do that. That's good because I still to this day have eyebrows. Blessed you made it out, you made it out of white to k with Listen. I don't have my nineties two thousand eyebrows, but I still have eyebrows. Fair okay, Doki.
Last question, who was your most stubborn client from Y two K? Doesn't mean mean or difficult, but who was the most stubborn when it came to like getting dressed or wearing what you recommended or you know.
When I think about it, it's like this sort of like the Lindsay Miss Nicole. We had so much fun, so they weren't. I'm thinking about my music world, Like I mean, Brittany, I would say definitely was the one who would sort of like change from whatever my well after you told me that cutting the couture story. Yeah, I mean I think Brittany was definitely probably the one that you know did that. And I think I'm thinking about some of the Backstreet boys, like we really collaborated.
I mean, AJ and I had so much fun because he was the most like out there, you know, yeah, would he was the most costume me.
He was like a he was like the well, like the bad boy of the back show for sure.
So he was like the Risks taker, Yeah right, the most incredible voice. And Kevin was like dressing like my brother. It was fun. It was like chasing him to put clothes on him. Oh my god, that's I mean, because he's just like running around enjoying. And Brian was like a gentleman, you know, and Howie was a doll.
Okay, this is your final question. What was your go to look in the Y two k era when you were on set, when you were traveling, when you.
Were black and jeans, Like I would wear dark jeans, I'd wear light flare obviously. Yeah, always dark and some kind of like black, probably ankle boot, you know, some kind of boot and like a like a like a black like leather jacket. I had like a hundred black leather jackets and that was like my jam, your go to. Yeah, stylists always need pockets. Yeah, I think of it so funny. Pocket it was so fast. I'd like think about what
I was even wearing. I can't even like, yeah, I never thought about me right, well, because you said you like I kept a suitcase pack, so you're just like bringing the same things over and over. I'm sure, so weird. I flew a lot of private planes. I remember. Oh that's fun though. I was on private planes very young.
Did you witness anyone have a total meltdown on a private plane?
Of course I did spill it. Nope, who ever, honey, I witnessed more meltdowns between ninety eight or ninety seven and two thousand and eight. Seven, twelve, my wheels are turning, and thirteen my styling wave was filled with melt.
We're at our time for today that you have just said, you have just cued us up for Part two Meltdowns.
Yeah, Part two of this podcast, the Meltdown, The Meltdowns. Thanks for listening everyone, all right, everybody, thank you so much for listening to Climbing and Heels. If you haven't already, please subscribe to the show on Apple Podcasts, Spotify, the iHeart app, or wherever you get your podcasts. You don't miss a single episode this season, and be sure to follow me on Instagram at Rachel Zoe and of course the show at Climbing in Hills pod for the latest
episodes and updates. I will talk to you so soon and have a great week month