rst time, I am told, that a journalist has
seen where she lives. I arrive a few min-
utes before our appointment on a Friday
afternoon, and her doorman—make that
super doorman—waits until the precise
time to let me onto the elevator. Weiss
greets me with a hug, wearing an over-
sized blouse, a knee-length skirt, and
slippers. Her assistant, Stacy, is answer-
ing email at a long table festooned with
the same sculptural oral arrangements
found at the company headquarters.
There is no publicist.
From the windows of Weiss’s living
room, you can see the Glossier oce.
That doesn’t bode well for work-life
balance, but she swears the proximity
allows her to sleep in (she’s not a morn-
ing person) and walk to work. It’s a rental
apartment, heavy on natural light, with
the same white, pink, and red palette
as one of her thronged pop-ups. In the
bedroom, laundry is air-drying on a rack
in the corner. Over her low-slung bed,
there’s a Glossier photograph of lips that
looks like a Marilyn Minter; outside in
the living room, there’s a real Marilyn
Minter—a painting of a woman’s face
behind steamed-up glass. Weiss shows
me the tiny guest room where she has
painted the lower half of the walls a
shade of buttery yellow, in homage
to chef Frederik Bille Brahe’s Apollo
Bar in Copenhagen.
The long table is where Weiss likes
to have people over for brunch, mostly
bagels she picks up from the old-school
delicatessen Russ & Daughters. (“I did
try keto, but it made me feel kind of dead
inside.”) She tells me she has “basically
ve friends,” who met in Florence while
studying abroad. “Even when you’re a
student, it’s still such a rat race as soon
as you get to the city. Every single person
who comes here is like, ‘I’m a tiny adult.
I want to work and get an internship.’ ”
“Including me,” she acknowledges.
Weiss doesn’t cook a whole lot, but
today we are making a salmon and goat
cheese frittata from an Ina Garten recipe.
It’s for one of those ve friends, who just
had a baby. “And I’m freezing my eggs,”
she says with a self-deprecating laugh, as
she starts to heat the onions in butter. I
half wonder if she’s invested in an egg-
freezing start-up as the next millennial
frontier (the ads on my Instagram sug-
gest a booming industry), but her review
of the experience suggests not. “I was
super bloated and looked four monthspregnant. I gained 10 pounds during a
three-week period,” she says.
This is a very dierent bodily state of
affairs from the much-talked-about
beauty guide that she posted in 2016.
“The Little Wedding Black Book” revealed
the depths to which she had gone—colon-
ics, microcurrent sessions to lift her face,
“subtle” lash extensions—to look her
best for her destination wedding in the
Bahamas, attended by 37 guests. The
fallout of her short-lived marriage to
photographer Diego Dueñas is far less
talked about than the post itself, which
has been lampooned as an apotheosis
of extremes—which is both true and
unfair, considering that testing beauty
treatments is part of her job. “I actually
loved the dialogue,” she says. “That’s
exactly the conversation around beauty
that we should be having: Does this make
you frivolous? Does this mean you’re not
a caring person or a socially conscious
person?” She pours the frittata mixture
into a pan, deeming it a little smaller than
she’d like. “There’s no level of mainte-
nance that’s actually okay.”
Weiss doesn’t mention her ex-husband,
but she moved into the SoHo apartment
alone and started tagging Will Gaybrick,
her current boyfriend, on Instagram
this past January. Even though she posts
as frequently as you would expect of a
young CEO (another topic she won’t
discuss: how much of the company she
owns), her 500,000 followers glean
very little about her inner world from
her vacation sel es and broad support
of reproductive rights. She sees her
privacy as a kind of political stance. “If
you’re reading stories about male found-
ers, it’s rare to have as much intrigue
around what they’re wearing,” she says,
explaining that she sees herself between
two worlds. “People often ask, ‘Are youa tech company? Are you a beauty com-
pany?’ And I say, ‘Yes, we are.’ ” Still, she
adds, “Women are so hungry to have
more role models who have achieved
what they want in their careers.”
Her trajectory could have followed
a dierent course. In her Into the Gloss
days, she modeled in Derek Lam’s look
book and kept up her signature platinum
hair. Since then, she has mostly stopped
going to fashion events and no longer has a
dye job that requires laborious touch-ups.
We talk about the parallel universe where
Weiss is an inuencer instead of a CEO. “I
would be at the Valentino dinner right now
with [Danish stylist] Pernille Teisbaek and
all those girls, who I love.” She smiles a
little dreamily, or maybe in relief.
There’s a vulnerability to Weiss’s
transformation away from fashion dar-
ling to a woman in her mid-30s trying
to gure out her life, like so many of us.
Of course she doesn’t have it all. The
third part of the Glossier slogan (“Smile
Always”) is the hardest one to master,
especially when you’ve made it to the
top. Besides, is that mandate of perpetual
cheer setting the bar too gratingly high?
The brand’s sheen of optimism can occa-
sionally give o a saccharine aftertaste.
But, in the right light, “Smile Always”
isn’t a denial of real-life complexity (girls
who tag Glossier in their moody sel es
prove as much) but an upbeat allowance
to fake it till you make it. It’s the wellness
era’s version of dressing for the job you
want. Weiss is doing her own dabbling on
the self-care front. She disappears into
her bedroom to fetch a gratitude journal
she writes in for ve minutes each day. I
imagine super intern Emily would have
stied a laugh if the words gratitude jour-
nal had ever come up.
But Weiss knows where her young
audience is going. She has personally
invested in the Co-Star astrology app—
an addictive thrill in this second age
of Aquarius. She is also nurturing the
next generation of Emilys, investing in
Supersystem, a political-platform start-
up from her former assistant, Morgan
Von Steen. It seems inevitable that a
Glossier book—part self-help, part suc-
cess tale—could be on the way. Weiss
has plowed through the genre over the
years (they helped, she says, but no
book can tell you how to be a CEO), and
I scan the shelves of her color-coded
library. (In the white section: Small Fry,
Sensemaking, CONTINUED ON PAGE “People often ask,
‘Are you a
tech company? Are
you a beauty
company?’ And
I say, ‘Yes, we are.’ ”NOVEMBER 2019 VANITY FAIR 141HAIR BY KEVIN RYAN; MAKEUP BY YACINE DIALLO; TAILOR, MARIA DEL GRECO; FOR DETAILS, GO TO VF.COM/CREDITS