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 an editor 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 different from me at that age.” (High praise from Chen, herself an early bloomer who was tapped to edit Lucky at 33.)
By the summer of 2010, Weiss—then a fashion assistant at Vogue—was relaxing on a Connecticut beach with her family when she dreamed up a beauty blog called Into the Gloss. Back at the office, in search of a sounding board, she asked Chen if she could have a word. “She closed the door, and I was like, ‘Oh, this is serious,’ ” Chen recalls. Weiss wanted to start a website that would show the real-world beauty routines of fashion insiders and celebrities—stuff that she learned on shoots, like Karlie Kloss’s devotion to Bag Balm ointment on her lips. Weiss bought a $750 used camera and the domain for intothegloss.com, and by September the first post went live, with publicist Nicky Deam sharing her Fashion Week survival items.
The site’s Top Shelf column gained an immediate following. In it, a famous or at least cool person chronicles their grooming routine in sprawling detail, striking a tone that feels voyeuristic, useful, and democratic. Jenna Lyons may have had a makeup–artist friend bring her back Canmake Cream Cheek from Japan, but she also praised Blistex Medicated Lip Balm. (This summer, before her best-selling essay collection debuted, Jia Tolentino mock-cursed Tatcha’s cleansing oil in her Top Shelf: “It’s so nice, and it’s so expensive. Kill me.”) By early 2012, the site had more than 200,000 unique visitors per month. By May 2016, that number had swelled to 1.3 million.
“I got a master’s in the state of beauty through Into the Gloss,” Weiss says, describing “all the weird hang-ups people have about beauty, and the double standards.” She has spent a lot of time reflecting on its broader role: “how beauty can start conversations, how beauty can break down walls, and how beauty is something that every single person everywhere in the world deals with. It’s really foundational to who you are and how you relate.” In 2012, she tapped former Elle staffer Nick Axelrod to be the site’s editorial director, anchoring its place in the crowded new-media landscape. (Axelrod split with the company shortly before Glossier launched. He demurred when asked to comment—but, then again, he’s busy with his own Insta-bait body-care line, Nécessaire.)
Weiss had plenty of fashion types on board, but she soon learned that Into the Gloss was an all-access pass to powerful people. “I could not only meet Arianna Huffington, but go into her bathroom, spend two hours with her, and, in turn, make her feel really seen and heard—because she reads the article that I painstakingly edited from 4 a.m. to 8 a.m.”
More than that, as Into the Gloss drew an avid readership, it also amassed potential customers: beauty obsessives who were all too willing to discuss what kind of products they longed for. In other words: prime market research. Weiss noticed that the beauty conglomerates had a top-down way of communicating—via celebrity ads or department store placements. She knew, from the flood of comments on social media, that her largely millennial fans preferred a more conversational approach. Before the phrase “direct-to-consumer” rolled off the tongue, that’s exactly what Weiss had in mind.