Born to an executive father
and a stay-at-home mom,
Weiss grew up mostly in a
small enclave of Connecticut,
a precocious fashion obsessive in a land
of lacrosse players and manicured lawns.
The rst step toward her future life was,
ittingly, a glossy: Condé Nast’s Teen
Vogue, where she super-interned during
college. (When I bring up The Hills, Weiss
groans, and I don’t blame her. I too would
cringe at being associated with a reality
show best known for mascara
tears and an alleged object of
desire named Justin Bobby.)
Out of the gate, Weiss proved
to be indefatigable, balancing a
full course load at New York
University and part-time work
at Chanel with her magazine
duties—behind the scenes and, often, in
the pages. To Teen Vogue readers, she was
the pretty brunette who wore a vintage
dress to prom. To Eva Chen—at the time aneditor in the beauty department
and now Instagram’s director
of fashion partnerships—Weiss
“had that X factor. She was a
college student who clearly had
a plan, so pulled together and
focused, which was so differ-
ent from me at that age.” (High
praise from Chen, herself an early bloom-
er who was tapped to edit Lucky at 33.)
By the summer of 2010, Weiss—then a
fashion assistant at Vogue—was relaxingGENERATION G
Weiss with
the store’s “offline
editors”: Ernest
Brockenberry,
Allie Walsh, Sean
Fitzgibbons,
Maggie Dunleavy,
Jaitra Raju,
and Anjie Pitre.
Weiss’s clothing
by Isabel Marant;
shoes by
Jacquemus; earrings,
bracelet, and ring
by Sophie Bille Brahe.NOVEMBER 2019 VANITY FAIR 139