"Glamour has always been something that’s instinctual to me. I was always attracted to it in some way. I started working pretty early—at 14, I got a job at Contempo Casuals, which was this store where I thought all the pretty girls worked. They sold really flashy clothes, and for someone like me that loved glamour but lived in an area that wasn’t so glamorous, it was a joy getting on the bus and going to work. By the time I was 16, I was the assistant manager. You learn a lot working in retail, but by the time I was done with college, I wanted to move to the other side of fashion.

When I finally got an internship at a brand, I was super excited because I thought I was just going to walk into women’s design, find my calling, all that. But they put me in the mailroom! I was frustrated at first, but I learned where you can overnight packages, which FedExes are open late, and operational stuff that’s really helpful. By the time I got into marketing and design, I was really good at noticing company needs. It’s that sort of skill that makes you invaluable at work because I started making people’s lives easier. And so I like to emphasize to my girls—and I wrote about it in my book—figure out what it is you love, find where there’s a need, and fill it. That's how you become needed, and there’s nothing better than becoming needed in an arena that you love.

MAKEUP
Growing up, my mom was my version of Grace Kelly. When she was getting dressed up for different events, she had one thing that I thought was amazing. It was a trench coat that she wore as a dress with a snakeskin belt—probably faux. She didn’t wear a lot of makeup, but she wore a bright red lipstick. And Chanel No. 5 perfume. She was quite demure and quiet and I thought she just looked so elegant. And I also thought she commanded respect.

I have a face that can take a lot of makeup—I have so much fun with it. But if I’m not doing a photoshoot or if I’m not in front of someone, my makeup look will just be mascara. I love Estée Lauder Turbolash. There’s a little motor in it that makes it vibrate to make the lashes look quite long. And I fill in my eyebrows with a Charlotte Tilbury Brow Lift. Super easy. She actually personally taught me how to brush them out so it kind of looks more natural. The goal is to have the Brooke Shields eyebrows, so that product is important to me. Charlotte also makes a good nude lipstick for me called Penelope Pink. For contour, I cut my face in half for sure. I use the Charlotte Tilbury Bronze and Glow Powder. It’s actually a pretty universal shade.

SKINCARE
For a long time, I was someone who would sleep with my makeup on. It’s what happens when you’re just exhausted, working so late. But I recently started cleansing at night with wipes—it feels really good and it’s easy. I just pick up a pack from the drugstore. And always something gentle… Ones that promise too much tend to sting and I don’t like any of that. My skin is really sensitive.

My morning starts with Natura Bissé. The C+C Vitamin Cream in the orange jar is amazing. It’s easy to have something be too greasy under makeup, but this works really well before my routine. Since I started using it, my skin looks better. And I’ve been using masks also—that’s something I love to do. I like the Guerlain Super Aqua Eye Patches. They're kind of pricey, but they honestly make a huge difference.

HAIR
I only colored my hair once, and I regretted it. You really have to make a commitment to maintain it. At that point, I just wanted to know what I would look like as a light brunette, but it wasn’t a good look for me. Now I go to Tracey Cunningham for a gloss, to brighten it, and then someone at her salon Mèche cuts it. On occasion, I do get oil treatments where they put oil on your scalp row by row and then massage you for 30 minutes. It’s amazing because my scalp gets dry. That’s why I only wash my hair about once a week. I’m a dry shampoo girl because of that. I can get a blowout to last me a whole week. If I get it styled, I like braids or a ponytail. I like it done really high and tight because it gives your face a little lift.

HEALTH
Apa is my dentist, and he’s very chic. He does veneers and re-created mine when I fell after having Tallulah, my eight-year-old… He’s an artist, because he looked at pictures, created what I had, even gave me the nuance in my teeth. And so when he came up with all this stuff called Apa Beauty, I was really proud of him. I keep the lipgloss in my purse and then there’s a whitening kit that works on teeth that I appreciate, obviously.

I used to take Emergen-C every day while traveling, but they’re filled with lots of things that don’t actually help your health. 8 Greens kind of does the same thing but it’s all-natural and filled with greens. I’m not sure how they get that all into a little pill, but you feel the same as you do with Emergen-C, but I think it’s a little bit better for you overall. And then I do yoga twice a week and I workout with a trainer less than that, whenever it’s conducive to my schedule. I do put my work schedule first, which I shouldn’t. Sometimes I schedule in yoga like it’s a meeting on my calendar actually. It’s too good for your mental health to skip."

—as told to ITG

Rachel Roy photographed by Tom Newton in New York on February 16, 2016.