Anna Weyant has come a long way in a short time.
She was 24 when that first show opened, full of blond innocence and extremely shy.
There was a healthy dose of mischief and humor in Weyants paintings.

ROOM WITH A VIEWWeyant, next to her painting of Kaia Gerber, wears a Versace cardigan and top. Levi’s jeans.Kaia,2024, oil on canvas. Photographed by Jason Schmidt. Sittings Editor: Edward Bowleg III.Vogue, December 2024, Special Issue, Guest Edited by Marc Jacobs.
Weyant has conquered the art world instead of being swallowed by it.
She shows with theGagosian gallery(the youngest to do so), which is also Currins gallery.
John was the reason I started painting figures, Weyant tells me.

FULL FLOWERIt’s a Heartache, 2023. Oil on canvas. Photo: Rob McKeever. Courtesy Gagosian.
I saw one of his paintings in my second year at art school, and it changed my life.
And then there is the careful way she has navigated her relationship with her gallerys founder and owner.
Weyant and Sprout, her King Charles spaniel, left Gagosians house while he was vacationing inSt.

FRAME OF REFERENCEGirl in Windowby Anna Weyant, 2024. Oil on canvas. Photo: Maris Hutchinson. Courtesy Gagosian.
It was really stressful, she tells me.
I wasnt sure if we were going to be able to work together.
But their professional relationship remains intact.

DOUBLE TAKEWeyant often paints her friend, the podcaster Eileen Kelly.Two Eileens,2022, oil on canvas. Photo: Rob McKeever. Courtesy Gagosian.
Our friendship is very strong, Gagosian tells me.
Shes a great girl.
I love her as a human being.

FIRST TASTEBite,2020, oil on linen. Photo: Rob McKeever. Courtesy Gagosian.
The aging Sprout lounges comfortably in her arms.
She is startlingly pretty, with big dark eyes, perfect skin, and lots of blond hair.
Sometimes it works, and sometimes it doesnt.

TABLE FOR TWOIt Must Have Been Love, 2022, Oil on canvas. Photo: Rob McKeever. Courtesy Gagosian.
FULL FLOWERIts a Heartache, 2023.
Photo: Rob McKeever.
Shes more marble than flesh, more sculpture than painting.
Shes a still life.
The show is a little bit sad, she tells me.
Ive been feeling pretty low and a little bit pissy about painting.
Its maybe not as sexy or silly as some of my past shows.
Its the hardest show for me to do.
She begins to tell me about her past.
She was born in Calgary, Canada.
I say that with so much love.
Im probably more like my dad, a softy.
Im pretty soft, until I have to be hard.
She is the second of three children and the only girl.
Even Bear, the familys beloved cairn terrier, was a boyhis name is discreetly tattooed on her hip.
Just the three of us.
The professor wrote my mom a letter saying that I was good, she says.
I hadnt ever been told I was good at anything, and it meant so much to me.
Back in Calgary, she took an after-school class.
Her paintings at the time were really gunky, thick, and figurative.
She had seenLucian Freuds obituaryin the local newspaper, and she started trying to imitate his work.
My paintings were just so awful, Weyant says.
They lacked form and light and shadow, because I didnt really know how to paint.
She wanted to go to college in America, close to New York.
The Rhode Island School of Design (RISD) wait-listed her.
I didnt have good SAT scores.
I knew I wasnt such a strong candidate, and I respected them for wait-listing me.
FRAME OF REFERENCEGirl in Windowby Anna Weyant, 2024.
Photo: Maris Hutchinson.
At that same time, theNew Yorkmagazine art critic Jerry Saltz posted nine of her works on his Instagram.
All this set the stage for her debut at Riness gallery a few months later.
Their faces spring out from dark backgrounds, taking us by surprise, and often making us laugh.
The girls are all Weyant, sort of, discovering herself.
I reset a lot of things in my life, Weyant says.
I felt pressure, but never rushed, which was really special.
(Two years later it was up at auction, where it sold for $1.5 million.)
DOUBLE TAKEWeyant often paints her friend, the podcaster Eileen Kelly.Two Eileens,2022, oil on canvas.
Photo: Rob McKeever.
In the summer of 2020, Larry Gagosian bought two paintings that Weyant had held back for herself.
Gagosian, whom she had not met yet, invited her to his Los Angeles house for dinner.
He said he wanted to show her work in New York.
I was hesitant to leave, she tells me of the decision to switch galleries.
But its tough to say no to Larry.
I was so mesmerized by him.
The weekend also marked the start of a romantic relationship.
Weyant ended up leaving Blum & Poe.
That same month her 2020 paintingLoose Screwsoldfor $1.5 million at Christies.
(The dimensions of her canvases mimic the ratio of aVoguecover.)
Kaia was almost like butter in front of the camera, Weyant later tells me.
It was just so smooth.
And her energy was very soft.
The experience was nothing like what I expected.
I was just a little nervous because I tend to gravitate toward fuller faces.
FIRST TASTEBite,2020, oil on linen.
Photo: Rob McKeever.
HerVoguecover is due on the same day as the London show.
A few drops of blood well up from a cut on her left calf.
Because her studio is so small and so tidy, she moves finished paintings to the bathtub.
She shows me a seventh painting, which she has decided not to include and has since destroyed.
The image of Gerber is still in a very early state.
Weyant works quite slowlyeach painting takes her at least a month.
She collects shoes and purses.
She loves watching rock climbing videos of Jimmy Chin and Alex Honnold free-soloing.
On September 25, one day before her Gerber cover is due, she texts me, Finished!!
Yay and attaches the image.
Its aVoguecover, if Ive ever seen one, but its also vintage Weyant.
Gerber is looking sideways, not at the viewer, and shes clearly thinking about something fairly complicated.
I wanted her to look calm and wise and knowing, Weyant tells me.
It was really tough to get her likeness!
Its not usually something I have to even consider when painting a figure.
But it was a welcome challenge.
TABLE FOR TWOIt Must Have Been Love, 2022, Oil on canvas.
Photo: Rob McKeever.
Underneath the word lies a bouquet of three white flowers wrapped in brown paper.
It looks like its been thrown down on a stage.
Curtains-down, throw-the-flowers kind of thing.
Everyone can move on.
The cover is done.
The paintings are on their way to London.
(Once again, all of them sold before the show opened.)
Painting helped me heal, probably a lot more than I even realize now, she texts me.
I want to try one with a lot of blue and purple.
In this story: tailor, Jacqui Bennett at Carol Ai Studio.