Amanda Lepore

Amanda Lepore photographed by Emily Weiss

"I always felt like a girl. My parents in New Jersey weren’t exactly encouraging, but my grandmother was very open-minded. She had lots of costume jewelry and a big chest of purses and things, and she would let me play with all of it—even her makeup and perfume. She just didn’t care. Everything was okay until I started having gym class in school, and they separated the boys from the girls. I started to feel punished when I would be made to do stuff with the boys. When my parents cut my hair, when they wouldn’t let me take ballet classes, I felt like I was being tortured, and I felt ugly. I really envied the girls in my neighborhood.

Luckily I had very girly features—I was tiny and extremely feminine. Even when I dressed like a boy, substitute teachers would have to ask, ‘Is that a boy or a girl?’ They didn’t know. My brother started dating a girl who had a twin sister, and they would bring me along so the sister would have someone to hang out with. I became really close with them. They understood how I saw myself, so they would let me tweeze my eyebrows and taught me how to curl my lashes. They really encouraged it.

I found out about transsexuality in high school through a friend of mine who danced at a bar. We kind of knew about it from talk shows and stuff, but one of her coworkers was a transsexual. I went to talk to her, and told her I would trade her costumes I sewed for hormones! She just said, ‘You can’t tell your mother.’ I knew I wasn’t gay: I liked boys, but not as a boy. I had a woman’s mind. After starting the hormones at 15, my skin got really clear, and I slimmed out in some places and got curves in others. It happened quickly. I would always ask my mom for a sex change, but she refused. I had really nice girl's clothes and everything, started wearing push-up bras to kind of push up what I had, so there would be cleavage there. So, by my sophomore year, I just started to go as a girl to school. I thought, ‘What’s the worst that could happen?’ None of the students really bothered me, but the school actually told me I was too much of a distraction. My guidance counselor actually said to me, ‘Well, you can quit when you turn 16. Do you just want to quit?’ I told them I wanted to get my diploma, so they gave me a private tutor who would come to my house.

My grades actually went up, so my father let me go to beauty school part-time, and also sent me to a psychiatrist, who prescribed me hormones because he didn’t want me to self-medicate. I would go to the plastic surgeon every month to get hormone shots, blood work, and check ups. Eventually, I did get a sex change, and there's a whole story there. It didn’t hurt when I got it done at the hospital. But they give you a dilator as part of the healing process, which you have to keep in for extended periods of time to stretch the vaginal opening. It felt like a knife. It was the most painful thing I had ever experienced.

Rather than emulate the girls I grew up with who made fun of me, I decided I wanted to look like a movie star. It was like an escape. I did so much research, reading books and watching movies about Jean Harlow, Marilyn Monroe, and all of those Hollywood blondes with the boobs, the hips, and the heels. Everything was so exaggerated. Marilyn even had plastic surgery in the ‘40s—a nose job and had her hairline done, and it was a total transformation. Not so different than a transsexual, really. She made herself into what she wanted to be. She would do little things, like put cotton under her top lip to make it look fuller. I based my lips on Jessica Rabbit.

I’ve had my boobs done, and my lips done, my bottom lip reduced, and my bottom rib broken and pushed in—I think Raquel Welch and Cher did that, too. It’s illegal in the US, but I had it done in Mexico. They break the floating rib in the back and push it in, so there's no scar. Now, I get injections from Dr. Mark Warfel—he can soften your jawline and even your neck.

Anyway, once I moved to New York, I fell into the club scene. I worked as a go-go dancer for a week and Details magazine wrote a piece about me being an 'It Girl.' And when the press found out I was a transsexual, they liked me even more. I was in the Times, French Vogue... It was really validating. I became kind of the 'It' transsexual, especially after working with David LaChapelle, modeling in his photographs for years. He would always tell me that I was 'the number-one transsexual in the world with a fully functional vagina.' I became really proud of it. It wasn’t about trying to pass for a woman—I am anti that. I think it’s what set me apart from other transsexuals. It could have gone very wrong but instead it went right. Now, I host parties and perform in New York and around the world. I'm also taking voice lessons and recording music.

I am particular about my look. I always do my hair and makeup by myself. I will start with Ole Henriksen Perfect Truth CC Cream as foundation and I’ll use sponges to blend that in. Then I use an excellent concealer—Kevyn Aucoin Sensual Skin Enhancer. It’s really good to cover scars or under-eye bags because you can make it really, really thick, or you can make it really, really thin. But what’s really incredible is that it doesn’t photograph heavy or cakey at all—it will look dewy in a photo! For blush, lately I haven’t liked powders, so I use Kevyn Aucoin Creamy Glow in Liquifuchsia with a sponge. I really like cream blushes, because you can use a really bright color, like a red or different tones that you love, and you can fade it to nothing. After blush, I use Giorgio Armani Micro-fil Loose Powder—it’s a little more dewy and reflective than a white powder, so you look more flawless in pictures. Anything that is translucent-white either photographs dry or too white, and I’m really pale, so it’s good to have some kind of color on my skin. Then I highlight with MAC Lightscapade Mineralize Skinfinish in the same places that Marilyn Monroe did—the tip of my nose, the bridge of my nose, and my whole forehead to try to make my face more heart-shaped. I mattify that a bit with powder, and then I will dab more highlighter on my cheekbones, on my chin, and down my neck.  It’s like a heart.

The makeup artist Yadim taught me to lightly contour in the corners where your jaw meets your neck and drag it along your jawline. I heard Madonna does it, too. It’s great for strong jawlines. I use MAC Omega Eyeshadow to contour; it's also good to contour eyes. I put warmer, lighter colors toward my eyebrows and get darker as I go out. It makes your eyes look wider-set. I like a really white shadow on my eyelids—Make Up For Ever Star Powder—like Marilyn, and, for liner, I’ve been very into starting in the inner-eye crease with white and fading to dark at the wing. One of my good friends at MAC taught me how to do that. I love Clinique Bottom Lash Mascara, because it never clumps—I’ve used it for months and it never makes a mistake. But I use three pairs of false lashes, Ardell Double Up lashes from Duane Reade I like them to be really heavy! They're rubberized, so they won’t go cock-eyed when someone kisses you. I sandwich a pair between a full lash set and a flared set on top. It gives an ultra glam look.

On my lips, I like a bright red—not orange, not burgundy. But first, I use a lip liner to line my lips. I’ve been using MAC Cherry Lip Liner, followed by Sephora Cream Lip Stain in Always Red—it doesn’t move. For a darker color, I like Christian Dior Rouge Dior in Celebrity Red. I’m wearing that right now. It’s a little bit more blue. Then I always top it with Dior Addict in Little Red Dress.

Once I put my makeup on, it really doesn’t move. If I’m traveling, sometimes I will sleep with it on so that I don’t have to do it again—I’ll get off a flight and do whatever I'm doing with it on. [Laughs] I think it’s all about taking care of your skin.  When I take my makeup off, I use Pond's Cold Cream Cleanser followed by Ole Henriksen Truth to Go Wipes.

I was in a car accident in a taxi a few months ago, and ended up with some scars on my face, so I did a crazy amount of research and found Ole Henriksen Pure Truth Youth Activating Oil. The scars are really going away. I also put Ole Henriksen Sheer Transformation Cream all over my neck, chest, and arms, and it’s amazing for the scars, too. I love that company. The Lemon Strip Flash Peel has tightened my skin so much. It’s incredible. I’m a skin freak. To cover my scar, I put on Kelo-Cote Keloid Treatment. It dries into an invisible film and visually flattens the scar. Then you can put makeup on over it. Other than that, I just use so much sunscreen all the time.

My hair has been bleach blond since I was fourteen. I would have my friends dye it, but since I moved to the city, I’ve been getting it done every four or five weeks by Harlequin at Dramatics on 5th avenue. I’m loyal to him—he knows my hair and what it can take. I use a lot of Shu Uemura Conditioner and Essence Absolue to keep it hydrated. Bleaching gives you high-maintenance hair. To style it, I like a very light hairspray—Nioxin Niospray, because it brushes out, so you can go a few days without washing. And I set it in rollers. I usually wear a synthetic wig, too, in addition to my hair. I've found that synthetic wigs photograph whiter and less yellow than other wigs. I use a Bumble and bumble Hair Powder in White before I do my makeup, and then baby powder in the wig. It mattifies the wig to make it look more human.

My style hasn’t changed too much since my teenage years, either. I still hate baggy clothes. I like to see a tiny waist, whether it’s through a belt, or a corset, or tight clothes. Even if I go to the gym I will wear tight leggings and a t-shirt. I think it’s important to keep a consistent look—it makes you iconic. Of course, I always want to improve myself. Maybe I’ll try a new kind of false lash, or play with my hair differently, but, I like to stay recognizable. Someone like Lady Gaga who has so many looks could be impersonated and you would never know it wasn’t her! [Laughs]"

—as told to ITG

Amanda Lepore photographed by Emily Weiss in New York on December 4, 2013.

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  • olga, the teacher

    Immensely inspiring!

  • olga, the teacher

    Immensely inspiring, it's really great to skim through this Top Shelf. I am all into natural make-up, but Amanda is natural in her own way... a truly remarkable inspiration. Great idea, ITG!

  • Natalie

    Another great Top Shelf - I love the diversity of the people chosen. All come from incredibly different backgrounds and some aren't obvious choices, but none have ever been boring. In fact, most have been unexpectedly highly interesting.

  • eastvillagesiren

    Forget about the fake controversies in other, "ahem," mags and blogs. ITG is the smartest, sharpest, most diverse and most fun beauty/fashion/style leader. I learned some awesome tips from Amanda Lepore. Keep staying fierce!

  • Clever Girl Reviews

    Love this Top Shelf! Any chance we get a makeup application video out of it?

    • Elizabeth Licata

      I would love to see that contouring trick for strong jaws.

    • Vivdarkbloom

      That's exactly what I was thinking. Can we start a petition?

  • s

    i really, really love her. What a beautiful, strong person. And totally gorgeous.

  • Cat

    I'm always fascinated to read the Top Shelf's background story before their beauty routine, because sometimes the most interesting aspect is not so much the 'what' as the 'why'. Great profile to start out the week.

  • Kat

    I've taken yoga class with her a few times and 1) she smells like a miracle and 2) her skin is bananas. Amanda is incredibly successful at presenting a look that is so exaggerated it defies gender. Love her.

    • Sarah Diedrich

      I need to know how to smell like a miracle. Of this, I am most jealous.

  • Katy


    Okay, I'm gonna go back and actually read this now.

  • Masha

    Great Top Shelf! Really speaks to how make-up is a way for us to visually present our identity and how intimate our relationship with it is.

    Fun to read the part about maintaining a signature look…I see Amanda at my yoga studio sometimes and can attest that she is always beautifully coiffed and done up, even in downward dog!

  • Shawna

    So beautiful. Her skin is GLOWING. And I wonder if that ointment she used for scars would work for older scars.

  • Emma Hager

    I love this top shelf. Just goes to show that ITG realizes beauty is not just skin-deep. There are emotional and intellectual factors that a Top Shelf like this really proves. Keep up the good work, guys!

    Also, keep doing your thing, Amanda! You've such a fine-tuned eye! I especially love what you say about keeping a singular look and how that can make you iconic. Now there's a ringing endorsement for a personal uniform if I ever heard one.

  • Designer Binary

    OMG this is seriously the best article on here to date! I'm loving the diversity and think its refreshing, inspiring and forward thinking to see such an amazing array of all types of fascinating and interesting people on here. Your a breath of fresh air as a beauty blog and everything I've ever wanted to discover for myself being an avid makeup, skincare, health & beauty fanatic lol. So thanks :)

  • Rosie

    thank you god haven't even read this yet but love amanda

  • luxleesg

    loved this one so much. she's so inspiring!

  • PMD

    Hear, hear! Impressed that ITG isn't doing another article polling a supermodel. Please keep up a variety of interview subjects: ethnic diversity, gender diversity, sexual diversity, aesthetic diversity…maybe we can hear from some South Asians and people with disabilities, too! Great article, interesting subject, impressive incorporation of people outside the mainstream fashion loop.

  • CristalMeth

    I passed Amanda on the street once in the East Village. She did not look real, almost like she had been transposed on the scene from another time/place/dimension. It was truly fantastic, she does an amazing job of presenting herself, there is a great deal of power there. Nice to see her on this blog.

  • Folami Small

    Into The Gloss, THANK YOU!!! I first met Ms. Lepore as a wee club baby in my native NYC! She's one of the sweetest, kindest, and most unique people that I've ever had the pleasure of being acquainted with! Once again, I laud your blog for embracing the true notion of beauty... Beauty is much like the prisms reflected from a diamond- everyone might see something different, but it's undeniably there!!!

  • Kasia

    Incredible story, amazing read, great inspiration to become who you really want to be

  • murt

    Great top shelf!

  • lyz143

    Swooooooooooon I love her

  • kneelbeforetigers

    Amanda Lepore is truly a NYC legend... thank you for profiling this lady-on-the-scene!

  • Summer

    Omg I LOVE her! She is beyond stunning. Another win for ITG!


Ole Henriksen
Ole Henriksen Perfect Truth CC Eye Creme Broad Spectrum SPF 15
Kevyn Aucoin Beauty
Kevyn Aucoin Beauty 'Creamy Glow' Liquifuchsia
Giorgio Armani Micro-fil Loose Powder
MAC ‘Mineralize’ Skinfinish
MAC Eyeshadow
MAKE UP FOR EVER Star Powder White
Clinique Bottom Lash Mascara
Ardell Double Up Lash #206
SEPHORA COLLECTION Cream Lip Stain 01 Always Red
Ole Henriksen
Ole Henriksen The Clean Truth Cleansing Cloths
Ole Henriksen
Ole Henriksen Pure Truth Vitamin C Youth Activating Oil
Ole Henriksen
Ole Henriksen – Sheer Transformation Oil-Free Perfecting Creme
Ole Henriksen
Ole Henriksen Lemon Strip Flash Peel
Kelo-cote Advanced Formula Scar Gel
Shu Uemura
Shu Uemura Moisture Velvet Conditioner
shu uemura art of hair
Shu Uemura Art Of Hair Essence Absolue
Nioxin Niospray Hairspray with Lightplex, Regular Hold
Bumble and bumble
Bumble and bumble White Hair Powder
Johnson's Baby
Johnson's Baby Powder Original