Hanne Gaby Odiele wears a Fendi jacket. Beauty note: Chanel Rouge Coco Baume lip balm; Glossier Play Glitter Gelée in Glass Bonsai.

Photograph by Richard Burbridge; Makeup by James Kaliardos; Hair by Ward.

Hanne Gaby Odiele

Since being discovered at a music festival 15 years ago, the Belgian model Hanne Gaby Odiele has walked pretty much every designer catwalk there is. More recently, she’s become a tireless advocate for interACT, a nonprofit organization that promotes human rights for children who, like her, were born with intersex traits. “For me, it was very important to share my story,” she says. “Being intersex hasn’t stopped me from doing anything at all.” Compared to her celebrated bold street style, the model’s off-duty beauty routine is pared down. “Maybe if I come home from work with a great statement makeup look, I will keep it on for the night,” she says. The best part about the giant glittery eyes that Odiele rocks here? “They’re actually stickers, so they’re super easy to take off!”

Oslo Grace wears a Marni sweater; Wolf Circus necklace. Beauty note: Charlotte Tilbury Charlotte’s Magic Cream moisturizer (for all models, throughout); Tom Ford Traceless Perfecting Foundation (throughout); Kett Airbrush Hydro Makeup (on brows); Louis Vuitton Les Colognes in Afternoon Swim.

Photograph by Richard Burbridge; Makeup by James Kaliardos; Hair by Ward.

Oslo Grace

“I wanted to be everything I wasn’t allowed to be,” says the San Francisco Bay Area native Oslo Grace, who is transgender nonbinary and prefers the pronoun “they.” Grace isn’t into beauty culture, per se, “but I can pull off pink lipstick, even if I don’t like to.” For them, every photo shoot is something of a period piece. “I’m documenting the versatility that I possess now, because in five or 10 years I won’t look the same. An important part of my transition is allowing myself to change my mind in regard to identity and presentation.” Though they dream of shooting a Calvin Klein or Prada men’s-wear campaign, their most pressing goal is more personal: “To have a wife and lots of kids. I’m very excited by the prospect.”

Anna Herrera wears a Prada sweater; Alighieri necklace. Beauty note: Estée Lauder Advanced Night Repair Eye Concentrate Matrix; MAC Glitter in Pink and Lavender.

Photograph by Richard Burbridge; Makeup by James Kaliardos; Hair by Ward.

Anna Herrera

“I’m a kid from Brasilia, a futuristic, modern city designed to be the new capital of Brazil in the 1960s,” says the model Anna Herrera. “It sounds exciting, but really it’s just a boring town surrounded by some beautiful waterfalls.” Now based in New York, Herrera can more easily indulge in her two favorite things—film (she wants to study cinematography) and fashion. “Whenever I need inspiration, I watch Wes Anderson’s movies,” she says. “Or I study people on the subway. I like building narratives and characters just by looking at the way they dress and move.” Ambivalent about conventional makeup, Herrera relies more on her hair to make a statement. Thanks to a stylist friend’s encouragement over (numerous) cocktails, Herrera recently shed her long, dark locks in favor of a boyish crop. It was a career gamble that paid off in spades. “The short hair gives me way more confidence and presence,” she says. “It completely changed my life.”

Dilone wears a Bottega Veneta trench; her own necklace. Beauty note: Nars Blush in Gaiety; Chanel Baume Essentiel in Sculpting (on lips).

Photograph by Richard Burbridge; Makeup by James Kaliardos; Hair by Ward.

Dilone

“Transform, Dissolve, Repeat” reads Dilone’s Instagram bio, a credo she lives by. The Long Island native has been known to spontaneously buzz and bleach her brunette curls, and go from tomboy to glam in the blink of an eye. As she puts it, “We can create new versions of ourselves every day, shed the old skin, embrace the new, and do it all over again.” Dilone uses vision boards to help realize her constantly evolving desires. “I was visiting my mother recently and found my board from 2010,” she says. “Everything I had put on there became reality, including signing with an agency, walking for Victoria’s Secret, having a fab shoe closet, going to more family gatherings, and traveling the world. I went home that day and made another one!”

Hunter Schafer wears a 3.1 Phillip Lim blazer. Beauty note: MAC Paintstick in Landscape Green and True Chartreuse; Nars Dual-Intensity Blush in Adoration.

Photograph by Richard Burbridge; Makeup by James Kaliardos; Hair by Ward.

Hunter Schafer

Growing up in North Carolina, the transgender model turned actor Hunter Schafer never dreamed she’d be cast in a television show, let alone in HBO’s drama Euphoria, airing later this year. “I’ve been a visual artist my whole life,” she says. “If I wanted to see a character that didn’t exist in the world, I would draw it and make a paper doll.” A quick study, Schafer has already figured out that she’s more comfortable on set than on the runway. “In the entertainment world you can have a personality and be more provocative, as opposed to just looking like some standard of beauty.” She describes her dress code as “futch” (Shayne Oliver and Rick Owens are favorite femme-butch designers), and believes that less is more. “Earlier in my transition, I used to wear much more makeup, and I worked really hard to like my body and face. But now I’m at a point where I don’t need it to feel good about myself.”

Afra Cuéllar wears a Calvin Klein 205W39NYC T-shirt; Stella and Bow earrings. Beauty note: Makeup Forever Flash Color Palette in Artistic; Dr. Macrene 37 Extreme Actives High Performance Anti-Aging Cream.

Photograph by Richard Burbridge; Makeup by James Kaliardos; Hair by Ward. Producer: Jessica Daly at Art + Commerce; Production Coordinator: John Rodriguez at Art + Commerce; Photography Assistants: Peter Siskos, Scott Barraza; Digital Technician: Nick Barr; Fashion Assistants: Nicholas Centofanti, Katherine Nehra. Styled by Zara Zachrisson. Manicures by Maki Sakamoto for Chanel at the Wall Group. Models: Hanne Gaby Odiele at Women Model Management; Oslo Grace at BMG Models; Anna Herrera at Supreme Management; Dilone at DNA Model Management; Hunter Schafer at Elite Model Management; Afra Cuéllar at Silent Models NY. Casting: Edward Kim at the Talent Group.

Afra Cuéllar

The New York–based model Afra Cuéllar’s career path has been more circuitous than most. Crowned Miss Yucatán at age 18, Cuéllar then worked as an engineer for a telecom company. One sweltering day, as she was driving a company van to a job, she momentarily blacked out, and the van flipped over 10 times. She was lucky to survive, but was bedridden for two months with back and head injuries, and in constant pain. By chance, during her convalescence, she switched on the TV to a Victoria’s Secret show. “I know it sounds cheesy, but in that instant I knew I wanted to be a model,” she says. At castings in Mexico City, however, “people said I was too gay, too lesbian, too edgy, my walk was too ugly.” So Cuéllar grabbed a backpack and headed to New York, where she shaved her head and signed with an agency almost immediately. “If there’s anything I learned from the accident, it’s that you have to focus on your goals and be in the present, because you never know what can happen tomorrow.”