'I remember reading teen magazines growing up, and not feeling like anyone in them. I wasn’t blond—then; I didn’t have a boyfriend. That's when I had that idea to make Sassy, a magazine that would be for the kinds of girls that I felt like I was. I didn’t want other girls to go through what I was going through. I wanted them to feel cool with themselves the way that they were... It’s the one good idea I’ve had in my career, and I just keep doing it again and again in different mediums: creating a space where women can support each other in a judgment-free zone, and be themselves completely. That’s Sassy, that’s Jane, and now that’s xojane.com and our beauty site, xovain.com.

When I was the Editor in Chief of Sassy, I’d get flack from parents about stuff they felt was inappropriate to be saying to teenagers. The thing I would hear a lot was, 'If you were a parent, you would look at it differently.' I always had that in my head: ‘How will I feel about this if and when I’m a parent? Will I be saying the same kinds of things?’ My daughter, Charlotte, is ten now, and it’s amazing to finally have a tween. I want to tell her things exactly the way I would say them in Sassy. I like to expose her to everything. But, we’ll see how it turns out. She’s more into makeup than I am. She and a friend of hers got into wearing a full face of makeup when they were about seven—I would let her put it on and go around the neighborhood. I remember one day we were walking and someone said, 'Oh, you were at a face-painting party!' I was like, 'No… That’s just what she likes to look like.' I don’t believe in waiting for a certain age for anything: ear piercing, first date, whatever. I don’t get it, but that’s just me. I think kids know when they’re ready for things. What’s the harm in wearing makeup and playing around with it? People would say, 'Well, it’s not her, it’s how other people would perceive her or treat her.' I don’t know. I call myself the World’s Worst Mom, and Charlotte even jokes about it.

I didn’t get into makeup until my junior year of high school, when I went away to Phillips Academy Andover, a boarding school. I wasn’t like anyone at Andover. I was a scholarship kid. I might have arrived with a tiny bit of blush from the drugstore and maybe mascara, and I though that was 'wearing makeup.' That was the formative experience right there. Within the first couple of weeks, one of the girls in my dorm started to make a list of the pretty girls in the school. I was really dumbfounded. I had never heard anything like it. I was thinking, 'We’re all pretty.' I actually really believed at that time, because I had come from an upbringing where it was all very positive. My mom, an artist and a hippie, would talk a lot about beautiful women that we would see, but there wasn’t one beauty ideal. It was some inner-beauty or confidence she was responding to. I try to celebrate other women’s beauty in that way with Charlotte.

My first year at Andover, I felt like a loser. People didn’t know I existed and I was really depressed, so all I did was study. It was terrible. That summer I did a horrible—in retrospect—makeover on myself. I started wearing a ton of makeup and doing my hair, for hours, to look like Farrah Fawcett. When I went back to school, people thought I was a new student. I just went with it. I was like, ‘Why not? Why even remind them that I was that girl from the year before?’

Makeup was my crutch and addiction well through college. I wouldn’t go out without it. I even missed an exam one time because I didn’t have enough time to get ready. I went to Oberlin, and that was not the vibe there at all, but I was so stuck in that way of thinking. But it was taking away from other things I wanted to be doing, so I started toning it down. Just a little bit less, a little bit less, a little bit less. By my junior or senior year, I was little bit more easy-going about it, and now I’m very laid back.

I’m so not attached to what I look like now. Those years of obsession, checking myself in the mirror, like, twenty times a day, got it out of my system. Now, I’ll go out with my daughter, and she’ll be like, ‘You have toothpaste on your chin.’ I won’t have even looked in the mirror.

On a regular day, I won’t necessarily wash my face. If I didn't put any makeup on it the day before, then there’s nothing that needs to be washed off—that’s the way I think of it. [Laughs] I learned that from Genevieve Herr, the amazing makeup artist. She’s older than I am, and gorgeous, with amazing skin. She just doesn’t wash her face. If anything, she uses a little water. I was like, 'I can do that.' When I do wash my face, I love Tracie Martyn Amla Purifying Cleanser. It doesn’t fuck anything up and you don’t feel like you’re taking layers off of your skin or drying stuff out. I was given the Clarisonic, and I haven’t used it yet, but I will.

To moisturize, Murad Rapid Collagen Infusion makes my skin feel baby-smooth. I don’t know that it makes my skin look that much better, but I use that with Tracie Martyn’s Shakti Resculpting Body Cream on my face. One, it smells great, and two, it moisturizes without having any residual shininess or that oil-slick thing. I don’t know about the 'resculpting' part—I’m not really concerned about my body, but I am pretty concerned about my face. Clearly, I like Nu Skin NaPCA Moisture Mist because it’s almost gone. It’s an amazingly moisturizing spray that, again, leaves no shine or anything. I don’t like to feel like there’s something on my face, so mists are the kind of thing I can get behind. The Hydrating Antioxidant Mist from Kinerase is good, too. Courtney Cox, who’s an old friend of mine, was the spokeswoman for Kinerase for a while and she was giving me all of that.

If I’m getting my picture taken or have an event, I’ll use Tracie Martyn QuickFix Eye Pads. For someone who doesn’t take the time to do a lot of things, I actually take the time to do these because the collagen on them really works, and you can put them anywhere, not just under the eye. I cut them in half to get more out of them because they’re big.

I love products, but generally, I believe that how good you look is directly related to what you’re putting into your body. I drink apple cider vinegar on a regular basis. One of my beauty writers has amazing skin, and she told me that’s what she does, so I started drinking it, too. I also noticed that I look better when I mix this powder called ProGreens into juice and drink. I can see a really clear difference right away.

Makeup-wise, I wouldn’t say I’m really good at doing my own. I wish I felt more confident about it, and maybe it’s because I wore terrible makeup during high school, but I have other people do it now. I’ll even let anybody else on staff do it. At the beginning of Sassy, I would wet the makeup sponge and then I apply a little foundation with it. That was my 'thing.' Moving into Jane in my thirties, I started having Genevieve do my makeup. She would go do Anna Wintour’s face every morning at six. I slept late at that time, so she would come over to my place after—not every day, but as many as I could justify. She has an amazing trick that I call ‘butterfly fingers’ because she applies makeup with these really light, small taps of her fingers. I want to say that I learned that stuff from her, but I just knew I could get her to do it if I needed it. I do nothing to myself. It’s a preference and priority thing, because I consider working a more valuable use of my time.

For someone who doesn’t use many products, I use about ten on my eyebrows alone. I feel that full and thick brows make a huge difference now that I’m older. Anastasia Soare came and did my eyebrows at one point. But when I do my own, I always use the little stencil in the Anastasia Brow Express and fill it in. It totally works. The Anastasia Brow Wiz in Ash Blonde is perfect. I mix it with a Vincent Longo pencil, and then I’ll put the wax on after.

On my eyes, I apply MAC Shadowy Lady with a sharp-edged brush if I’m going to do any kind of liner, because it’s not too harsh and it’s not black. And I’ll put Vincent Longo Medium Number 2 Camouflage Cream under my eyes or wherever there’s redness. I’ll also wear a little MAC blush.

Before getting my picture taken or going on TV, I stretch out the sides of my mouth as hard as I can with my hands. It gives me a nice, wide, Julia Roberts kind of smile—you know, the smile when there’s a gap between the sides of your mouth and teeth? That’s my favorite look. I especially try to stretch the top lip because it gets a little fuller. On my lips, I wear Edward Bess Deep Shine Lip Gloss—his products are amazing. And I always carry a few different lip balms with me, like Laura Mercier’s.

I’m not good about accepting an invitation to an event that’s coming up in an hour. I like to have enough advance notice to schedule an appointment with the hair and makeup person I most want, and time to use my Far Infrared Sauna. My sauna has moved with me three times. I first tried it in the L.A. office of my amazing holistic doctor, Dr. Charny. You have to be careful to get exactly the right kind—the ones that Scientologists use when they’re detoxing. Tom Cruise donated a bunch of them to the rescue workers after 9/11 to get all of the toxins out of their body. It works with or without heat, but it gets up to 170 degrees. Your skin gets an incredible glow, and it makes you feel like you’ve been sitting out in the sun. The way that I understand it, it cleans you from the inside out, heating you like a microwave. I haven’t done it in a couple of days, but you can really see a difference.

When I have something really major coming up, I’ll go see Tracie Martyn. If I had the time, I would see her once a month, but I usually end up seeing her two days before a big event to get the Red Carpet Facial. She also has an LED bed that I try to take advantage of. That’s so right up my alley. It helps with mood and dry patches. What else...I’ll go get laser treatments for the bags under my eyes, which have come up pretty recently; it’s an aging thing. I don’t believe that anti-aging products do that much, but I’ve gotten every possible kind of laser treatment, because I can really see the difference.

When it comes to my hair, I’m particular about products. I won’t even use hotel shampoos and conditioners when I’m traveling. I always bring whatever brand I’m using at the time. I like these Oscar Blandi shampoo and conditioners because they really hold the color. Depending on how healthy my hair is, I can usually let it air dry, but I travel with my own blow dryer. Last year, I was going to England a lot for work, and, of course, I was bringing my blow dryer with me. I didn’t realize that the wattage is different there, so it actually fried my hair. I was like, 'It’s working so fast here. This is amazing!' Then I came back and my colorist, Kyle White at Oscar Blandi, said, 'What did you do to your hair?' It took a while to figure out the culprit. After I dry my hair, I put in Sheer Gloss or Hair Serum.

For fragrance, I have a bunch of Kilian perfumes, and sometimes I’ll steal my daughter Charlotte’s Love’s Baby Soft. Otherwise, I use a locally made fragrance that I bought at my yoga studio. It’s a hippie-dippy scent by Givescent.

The thing that changes me the most is exercise. I do Pilates three days a week and I do yoga as often as possible, because it calms me down and helps me put things in perspective. If I had time to do yoga every morning, I’d be more chilled out, feeling better, and not taking things too seriously. Plus, it has this Botox effect, making little lines disappear. I couldn’t believe it. For a quick aerobic workout, I also spin. I can get it done in 45 minutes, but then my mind is spinning after. It’s just about what works for you, everyone is different.”

—as told to ITG

Jane Pratt photographed by Emily Weiss in New York on April 9, 2013.