In 'I Love LA' Fashion, Next-Gen Striving Is in Style

Maia Simsbury, the aspiring talent manager played and written by Rachel Sennott on HBO's I Love LA, is a familiar working-girl archetype on paper. She's 27 but she still has an entry-level title (and salary). She's put in the hours for a promotion, but her boss, Alyssa, (played by Leighton Meester) shuts down her ask to finally graduate from her assistant role. It's all very 9 to 5 in theory. But set against a backdrop of influencers, ad campaigns, and raucous late-night parties, it's not so corporate in practice.

Maia spends I Love LA's eight-episode first season chasing success in a version of LA you won't recognize from reality TV. And, while wearing the opposite of heels and a cinched blazer dress. "It's not Kim Kardashian's LA," as costume designer Christina Flannery explains to Marie Claire. Rather, it's an LA populated by a new generation of strivers (at best) and clout-chasers (at worse), dressing the part in a range of It bags and vintage grails you'd more likely find on Depop than at a department store.

Flannery pulled inspiration for her leading lady from pop culture tentpoles of the 1990s and early 2000s: Cruel Intentions, Sabrina the Teenage Witch, and yes, some Sex and the City. The blend of baby tees and tiny skirts—plus a vintage Dior bag or Chloé dress—reminded the costume designer of the elevated-yet-offbeat style she's observed in LA neighborhoods like Highland Park and Silver Lake.

Maia is the character with the biggest arc by the season finale, in the script and in her wardrobe. On a journey where she's "blowing up everything"—her relationship, her professional connections, her friendships—her closet couldn't stay the same from episode 1 to episode 8.

"Maia to me kind of represents this like Saturn return," Flannery says. She's referring to the astrological phenomenon when Saturn reaches the place it was at someone's birth, marking a period of transition and rebirth. For Maia, that means a gradual evolution from "aspirational" florals and sweet kitten heels, in the image of her boss, to edgier, more confident clothing.

At the series' start, "Maia still has that cute, feminine feel to her and a vibe where she's trying to become the next boss at her job, and she's trying to pivot herself to align with Alyssa180 [the marketing agency] and Alyssa's character, specifically." In early episodes, vintage Betsey Johnson and dainty wallpaper prints are the cornerstones of her closet. She and Alyssa even style different versions of the same Laura Ashley-esque top at the same time.

Still, the Gen Z inclination to bend boundaries was present. "In the office scenes, I still wanted her to have a little touch of fashion," Flannery adds. "So she's wearing a cute Marc Jacobs vintage cherry top, but underneath it she's wearing a vintage bullet bra that we sourced."

The more time Maia spends trying to promote her foil and star client, Tallulah (Odessa A'zion), the more her wardrobe shifts. Tallulah is a "take-no-shit anarchist" with a ripped up wardrobe to match. "She's stumbled into this social media thing, but she doesn't really give a shit about it, so we wanted to play with that within clothing," Flannery explains. "It's a cool, edgy, punk New York feel with a DIY twist on it." When Tallulah does wear something designer—like her Balenciaga City bag in episodes one and two—it's stolen.

By the series finale, Maia has temporarily traded Los Angeles for New York City—and some major (if risky) career prospects. Flannery calls Maia's touchdown on the east coast her "Carrie Bradshaw moment."

As Maia coordinates a high-stakes dinner appearance for Tallulah with a prestigious fashion brand and walks away from a manipulative offer from a toxic former boss, "You see a full transition for her in episode 8. Her color palette changes. Her hair changes," Flannery explains. Gone are the Betsey Johnson florals; instead, she's wearing a black feather-trimmed top with capris. In one scene, she even swaps outfits with her influencer frenemy-turned-client.

"I feel like that's a really pivotal moment for her," Flannery says. All season long, Maia's put everything on the line to level up her work life. In this episode, she dresses like it, too.

Viewers will have to wait until a planned second season to see how much business Maia and Tallulah manage to handle on their NYC business trip. Know that behind the scenes, Flannery and Sennott are applying the series' same hustle-at-all-costs energy to bring the series' distinctly LA style to life.

"I was reaching out and begging people, 'please send us stuff,'" Flannery laughs. She remembers the formula she'd follow to stretch the series' limited first-season budget as far as it could go: "Okay, this Chloé dress is so expensive and so amazing but it's such a statement piece, so then this outfit can be patched together from a thrift store or the rental house." Like the characters she dresses throughout I Love LA, she always hustled until she figured it out.