THE NEW YORK TIMES, SUNDAY, OCTOBER 25, 2020 ST 9siblings and her stay-at-home
mother moved for her father’s job
as a factory plant manager.
While still a student, Ms. Smith
got a retail job at the flagship
Hermès boutique on 57th Street,
which she parlayed into an intern-
ship with the brand in Paris. Smit-
ten with the French city and lan-
guage, she landed another intern-
ship at Louis Vuitton and then en-
rolled at ESMOD, the French
fashion school.
The next internship was at the
haute couture atelier of Christian
Dior on the Avenue Montaigne.
Ms. Smith worked on the second
floor, illustrating gowns in water-
color: one copy for the client, one
for the archives. “It was such a
dream,” she said.
Missing the energy of New
York, though, she decided to re-turn in 1996. She got an entry-level
job on the design team at Gallery,
an outerwear company. “I love
coats,” she said. “A coat is the first
impression you make.” She was
brought in by Mr. Oshrin, an exec-
utive on the company’s business
side who was impressed by her
portfolio.
By 1998, Ms. Smith moved to a
design role at Helen Wang, a con-
temporary brand. “It was a new
market sector that I was excited
about, with brands like DKNY,
Anna Sui and Rebecca Taylor. I
wanted to be able to create beauti-
ful fashionable clothing that I
could almost afford.”
She carefully tracked the
progress of her designs, sold in
the department stores that were
not yet seriously threatened by
e-commerce.
“The designs I worked on were
doing well and one even got on the
cover of a Neiman Marcus cata-
log,” she said. “It was building myconfidence.”
In 2000, Ms. Smith and Mr.
Oshrin, who had begun dating and
ideating, started Milly as a whole-
sale brand. “I handled the design
and creative aspects, and Andy
handled the financial side and pro-
duction,” she said. The business
plan called for Milly to do $1.2 mil-
lion in wholesale sales in the first
year. They hit the target in three
months.
“I think Michelle has always
done a great job at knowing how to
design in a way that is relevant
and shifting as things shift in
time,” said Tracy Margolies, the
chief merchant for Saks Fifth
Avenue.
Milly spread across the country,
to Neiman Marcus and Fred Segal
in Los Angeles. “We were coming
out of the minimalist ’90s with the
dark Prada and Calvin Klein
looks. What I was doing was super
colorful and printed with a little
ironic wink to vintage,” Ms. Smith
said. “It was totally different from
what was going on at the time.”
In 2011, Milly opened its store
on Madison Avenue and, a few
years later, another in East Hamp-
ton. Ms. Smith began to develop
close relationships with her
customers.
“I would go to the store on Madi-
son Avenue, and we would sit in
the dressing room and talk about
our bodies and our lives and ev-
erything women talk about,” said
Ms. Brzezinski, who hosts “Morn-
ing Joe” on MSNBC with her hus-
band, Joe Scarborough, whom she
married in a dress designed by
Ms. Smith. “Michelle can feel your
vibe and has an ability to help you
translate that into your own per-
sonal style that is just so spot on.”
But supplying the contempo-
rary market, which demanded
new product every month, could
be dizzying. “By the end, I was de-
signing 27 collections a year with
over 100 styles per collection,” Ms.
Smith said. “It was a crazy ca-
rousel, and it was going so fast.”
In 2013, the stressed-out de-
signer followed the advice of her
friends and started taking Soul-
Cycle classes. She especially en-
joyed those of Ms. Griffith, a favor-ite of Kelly Ripa and the former
trainer of Madonna who wrote a
book about going from alcohol and
drugs to fitness, “Two Turns From
Zero.”
“I couldn’t believe Stacey’s en-
ergy and personality and the way
she lit up the room,” Ms. Smith
said. The two became friends out-
side of class, collaborating in 2015
on a collection of T-shirts with Ms.
Griffith’s motivational catch-
phrases like “No One Remembers
Normal.”
But Milly’s expenses and debt
were growing as the brand tried to
expand its e-commerce footprint
while continuing to meet its de-
partment store obligations. Its
founders quietly decided to sepa-
rate while still living and working
together, but the situation was un-
tenable. “It just became a dys-
functional environment,” Ms.
Smith said of the company. “I don’t
think the right decisions were get-
ting made, because you had one
person who said ‘black’ and one
person who said ‘white.’ ”
Mr. Oshrin is currently working
as a apparel industry consultant.
“It’s a tough time to start any busi-
ness,” he said, “but Michelle is atalented designer and has tremen-
dous creative instincts.”
Ms. Griffith declined to be inter-
viewed for this article, saying that
she wanted the spotlight on her
girlfriend.The Two Michelles
At the end of 2016, Ms. Smith
heard from Meredith Koop, the
stylist for Michelle Obama. Ms.
Koop had been selecting pieces
from Milly for the first lady for
years, first buying things off the
rack and then working directly
with Ms. Smith on pieces like an
off-the-shoulder dress Mrs.
Obama wore on the cover of
Essence in 2016, and a prom dress
for Malia Obama. Ms. Smith “is a
woman who designs for women,”
Ms. Koop said in an interview. “It’s
a cliché thing to say, but it’s true in
her case.”
The white dress Ms. Koop
wanted for the official portrait
“was very authentic to what Mrs.
Obama would actually wear in her
personal life,” the stylist said.
Ms. Smith worked on sketches,
adjustments and pulled the dress
from her collection to keep it spe-
cial, but still wasn’t sure it would
be selected. “I had made coats for
the second inauguration that
weren’t chosen, so I didn’t think it
was a slam dunk,” she said. Its be-
ing chosen “was the most exciting
moment in my entire design ca-
reer.” (The dress will be on display
in the Smithsonian’s National Por-
trait Gallery exhibition “Every
Eye Is Upon Me: First Ladies of
the United States,” which opens
on Nov. 13.)
It is the only piece of her past
professional life that Ms. Smith
hangs on to, and she finds it irri-
tating when Milly’s new owner
seems to claim credit for the
dress, as it has on Instagram on
occasions like Mrs. Obama’s birth-
day. “It’s cheesy,” Ms. Smith said.
(“We bought all the assets of Milly,
and that dress is an asset of Milly,”
said Mark Friedman, the presi-
dent and chief executive of S.
Rothschild. “I feel bad that she’s
irritated, but she shouldn’t be.”)
In August 2018, Ms. Smith wasinvited to a barbecue in Montauk.
Ms. Griffith was there. “We both
felt really happy to be in each oth-
er’s presence, and we started
spending more time together,” Ms.
Smith said.
When the relationship became
serious enough to tell her chil-
dren, Ms. Smith said she over-
heard her son tell a friend, “Wait
till you hear this one: My dad has
a new girlfriend, and so does my
mom.”
Last year, the couple made it In-
stagram official, posting photos of
themselves in an embrace at the
New York City Ballet. Ms. Smith
captioned hers “#lovewins.”
Department stores are falling.
Fashion is flailing. Winter is com-
ing. But Ms. Smith’s wheels are
turning, and she finally feels com-
fortable in her own skin.
“Going through everything I’ve
been through, going from a young
woman to an adult in my late 40s, I
have found my own voice and my
confidence to freely express my-
self in my personal life and my cre-
ativity,” she said. “For the first
time, everything has aligned, and
it feels amazing and true.”Top: Ms. Smith, on the left, with Stacey Griffith at a party last year. Above,
from left: a look from Ms. Smith’s new line, which she is selling directly to
her customers online; and the Milly fall collection show in 2004.Michelle Smith in her Manhattan
penthouse, which also serves as her
studio and office.SIMBARASHE CHA FOR THE NEW YORK TIMES
DAVID BENTHAL/BFAVIA MICHELLE SMITH ÁNGEL FRANCO/THE NEW YORK TIMES.