"Nighttime dressing is not very different from daytime dressing for me. I feel like night clothes don't get a chance to live the way day clothes do, so I prefer to think of night clothes as day clothes. I used to get totally dressed to go out. I can think of one particular outfit and I don’t know why... I was at dinner at The Cupping Room, which is the last place you'd want to be wearing a pair of patent leather wooden heel platforms and a velvet bubble mini skirt. And yet I was, with this vintage Chanel gold chain belt that I stole from my mom. [Laughs] That’s a night look—you've got the velvet and the patent leather and the gold chain. And I had a cat-eye on! It was a whole look.

Now most of my socializing happens after work, so I have to think about what I'm wearing from 9am to 9pm, and the makeup follows. If I’m wearing something quite simple, like a plain gown or whatever, I'll go all out with my makeup—like a cat-eye and mascara and a red lip. I’ll wear red lipstick and I feel really cool when I do that, it feels like a look. One of my favorites is this Nars Audacious one called Carmen, and then Gucci actually just sent me a couple lipsticks and I’ve been wearing the red one a ton. I like it to be really bright—I feel like it suits my face better. I used to apply it on just one lip and smudge, or use a tissue to make it look like it was half rubbed off to get that French girl effect. But otherwise, when it's warm, I normally don't wear [face] makeup. I don’t like looking airbrushed—so no foundation or anything like that, just a moisturizer. I do like Nars' Casino Bronzer. Or something liquid, like Giorgio Armani Fluid Sheer. All about that sparkle.

You know what was so lovely—before the CFDA awards I had a makeup artist and a hair stylist from Glamsquad come and do me. With makeup artists, I’m very clear about what spots I don’t want them to touch—no undereye liner, no mascara, just leave it as bare as possible. It accentuates the bags. They’re hereditary and I’m fine with them, I'm relaxed. My features are really big. I’ve got big eyes and big lips, and a perfect nose—just kidding. [Laughs] But when I do anything, it just feels like a statement or very loud. It’s probably the way that a lot of women feel, like how women with bigger chests feel about wearing halter-tops or revealing tanks. When I do wear eye makeup, I like this eyeliner by Eyeko. I also use a Dior one, from time to time, because the felt tip allows room for error. And Boy Brow in Brown. I wear that every day.

One of the things that signifies that I’m going out is that I dab on more perfume on to smell nice. I wear Le Labo’s Thé Noir 29 and Byredo’s Rose of No Man’s Land. Those are my two scents. I like Thé Noir because it’s a little bit musky but not in a overtly masculine way. The Byredo is really refreshing, like this lovely floral, but with a surprising kick. It’s a little gummy-ish, it’s sweet. But not annoyingly so...it's like a wet gummy.

My anticipation going out is always hair down, but within five minutes of not being confronted by a mirror, it’s up. It’s just so much easier to throw it up into a little Cinnabon, I don’t even use a hair tie. That’s one of the great things about having long hair again. It’s also pretty thick and really curly, and I’ve been wearing it natural much more. But I have to do something to the ends, so I'll straighten them with a CHI Iron. I have a GHD one but I don’t know how to use it! I don’t know how to turn it on. The funny thing about my hair now is that I haven’t washed it since yesterday, before I swam in a pool, so it’s got some chlorine in it, too. I've been using AG Coconut and Argan Oil Shampoo and Conditioner a lot lately to wash it. And then I use Bumble and bumble Defrizz all the time because I have really frizzy hair.

There's nothing on my nails right now, but sometimes I use Dior Nail Glow. I think that having color on my nails is complicated because I wear a lot of rings and it just feels like too much. I don’t really differentiate, but I’m all about the accessories. My rings tonight are David Yurman and Shebee, and my necklace is from Aracano. This is a daytime wrist, an Aurélie Bidermann bracelet plus this friendship bracelet I got last week. It feels really fun with a black sheer dress—the one I'm wearing tonight is Dolce and Gabbana. I also feel like it would look really cute with a knit sweater in the winter because it’s like, 'I’ll never forget you summer.' Never let go." [Laughs]

—as told to ITG

Leandra Medine photographed by Tom Newton at her home in New York on August 15, 2016.