"I moved [to New York] when I was 18 to go to The New School. I studied Literature at Lang, but I was doing so many other things—I worked in retail, did some modeling, I was the office manager for a PR agency...a lot of jobs. Somewhere in the middle of this I met Jen Steele, and we started Girls I Know. The concept was to talk to all the amazing women we know in our lives ask them what they think about where they are and how they got there, and what happiness is and what success is. I loved doing those interviews. If you email someone and say, 'Hey, I think you’re awesome, can I ask you about your career?' very rarely are people like, no. Unless they're really famous. We emailed Beyoncé and didn't get a response.

While we did Girls I Know, I worked as an assistant at the Paley Center for Media—it's a media nonprofit in New York. I think being an assistant is extremely good foundational education for keeping your life organized, getting shit done, and knowing how to allocate time. You see how the system works and how it can apply to your own practices, which is extremely helpful. I brought some of that to Girls I Know and the other creative things I've done. Now I’ve been freelance writing and modeling and it’s going pretty well. I’m paying my rent! I just like being able to say yes to a lot of stuff. In this day and age, there are no one-trick ponies anymore.

SKINCARE
Recently I started doing this newsletter, "Things I Would Buy If I Didn't Have To Pay Rent." Vacations that I want to take, weird housewares I want to buy, but I have to pay rent. Like, I used to go get facials at Mario Badescu, which I really enjoyed, but then I started to feel like there is other stuff I would rather spend $70 on. Instead, I take care of my skin at home. In the morning I wash my face with Glossier Milky Jelly Cleanser. I don’t wet my face that much and it feels like I’m rubbing moisturizer into my skin which is really pleasant. I dry my face with a towel and put on CeraVe’s Facial Moisturizing Lotion AM with SPF which is really great under makeup.

Then I put on Clarins Beauty Flash Balm, it’s my favorite product. It’s really expensive, though. It’s one of the things I splurge on. If I don’t use it for two days, I notice a difference. The first time I got it I was at an Every Mother Counts event and it was in the gift bag. Christy Turlington probably wears it. Now I order it on Amazon for like, $5 cheaper. Or when I’m traveling abroad I’m like, “Yes! Duty-Free!” That's my secret, I think. After I put on the CeraVe and the Clarins, I brush my teeth and put on makeup. At night, I just use Mario Badescu Cucumber Lotion Toner and Glossier Priming Moisturizer.

MAKEUP
Half the reason I put on makeup is to feel like I’m making an effort and doing something, rather than because I feel naked without it. Depending on what my skin looks like in the morning, I either just do concealer, or I'll use Glossier Perfecting Skin Tint in Medium. I like it because it just blends in and I don’t really feel like I’m wearing makeup. Then I catch myself in the mirror and think I look really attractive.

My brows are really wild, I don't tweeze them or anything. When I’m on photo shoots they always ask if they can tweeze a little bit and I’m like, 'Nope.' It’s part of my look. I use this Milk Makeup Gel Brow Pencil in Brown to fill in and then Boy Brow in Black, but only on the edges to hold the longer hairs that go in all sorts of directions. Then, I have my Shiseido Eyelash Curler—my trusty tool. I didn’t figure out how to use this until maybe a year and a half ago. [Laughs] The whole concept of starting at the base and then going out, and also tilting my head back...that took a lot of practice. One time though, I did have my eyelashes curled by this amazing Japanese makeup artist on some shoot and she used a tiny hot spoon. I was like, 'Are you curling my eyelashes with a spoon?' And she was like, 'Uh huh.' Mind blown.

I have this mascara called Elf Volume Plumping Mascara which I think was like $3, but it works. It looks very natural, which is what I want to look like during the day. At nighttime though, fuck it... I have this Milk Makeup Weekend Lash Stain and it’s really intense. It doesn’t come off. I put it on the other weekend and I had it on for like three days! And then, if I want to do eyeliner, I have this one that I bought at Urban Outfitters last year because I needed it for Halloween, called Limecrime, which I had never heard of and didn’t know anything about it, but I like that it is a little paintbrush. So tiny. I'll also use Milk Makeup's Highlighter—it's really big, and you can't mess it up.

HAIR
I have really bad genetic dandruff. I try not to wash my hair that much, maybe once a week. I want to use Klorane Dry Shampoo because I like the smell and how it works, but it makes everything worse. Right now I'm using Aesop Calming Shampoo, it doesn’t really work but I feel obligated to use it because it’s really expensive. I bought it once and I was like, 'Well, now I have to use the rest.' It’s fine. I like it because it kind of makes my hair feel texture-y in a good way, instead of too smooth. You know what the best hair products are? The ones at the Chateau Marmont. Their shampoo and conditioner and lotion is all really great. I like using hair oils, Rodin Recine Oil is really good for me. I haven't gotten a real haircut in awhile—five years? My hair guru is this woman named Sera Sloane who has a salon called Lost Hills in LA. I trim my own hair until I can go see her.

NAILS
In college, I was obsessed with the old adage about lipstick matching nails and had Revlon's Hot Coral in polish and lip format. It was pretty cool, but I was the only one who noticed. Then I spent a really long time only painting my nails white, because I thought retaliating against nail trends was cool or something. I wore OPI Alpine Snow and Essie Blanc. It was a look, but I got tired of it. Now I'm wearing a lot of nude and pale pink colors lately, and I love a matte topcoat—Côte has a great one. My roommate taught me to keep my nail polish in the fridge. Evidently it keeps them from getting gross and goopy after a few months, so I do that. How long do you think people keep their nail polish for?"

—as told to ITG

Anna Gray photographed by Tom Newton at her home in New York on March 28, 2016.

Sang Bleu editor Reba Maybury explains her penchant for unconventional beauty, photographer Paola Kudacki appreciates good packaging (and, you know, good product, too), and stylist Ilona Hamer emphasizes the importance of an edited makeup collection in the Top Shelf.