Before landing breakout film roles in Superbad, Zombieland, and Easy A, Emma Stone made one of her earliest on-screen appearances in Malcolm in the Middle—playing Diane, a floral-top-wearing, backpack-toting mean girl whose mid-2000s style was as memorable as her attitude.
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At just 17, she guest-starred in “Lois Strikes Back,” the sixteenth episode of season 7, which aired on March 19, 2006—offering a rare glimpse into her pre-Hollywood fashion era long before she became an Oscar regular, a core part of the Spider-Man franchise, and a Louis Vuitton ambassador known for sleek gowns and impeccable heel choices.
Mid-2000s Teen Style: Floral Top, Corduroy Pants & Wedge Clogs
Emma Stone, as Diane, wears a floral blouse with lavender corduroy pants, a pink-trimmed backpack, and brown closed-toe wedge clogs—an unmistakably mid-2000s look that contrasts humorously with her character’s mean-girl antics in the episode (Credit: Fox)
The same year, she also appeared in The Suite Life of Zack & Cody and Lucky Louie.
In an interview with Interview Magazine, Emma explained that an experience on the set of Malcolm in the Middle convinced her to change her name from Emily Jean “Emma” Stone to Emma Stone.
Emma Stone appears as Diane in Malcolm in the Middle, a role she later credited with prompting her to change her professional name (Credit: Fox)
How a Confusing Moment on Set Led Emma Stone to Change Her Name
Emma revealed that her stage name came from a mix of practicality and panic. When Emily Stone was already taken at SAG, 16-year-old Emma briefly chose “Riley” — until a guest spot on Malcolm in the Middle left her confused whenever people called for “Riley” on set.
She ultimately switched to Emma, a nickname her mother always used. Years later, she joked on The Tonight Show that she originally wanted the name because of Baby Spice and avoided going by “Emily J. Stone,” despite loving Michael J. Fox, because she “couldn’t pull off the J.”
Early Hollywood Denim Era: Graphic Tank, Bootcut Jeans & Heeled Sandals
Emma Stone pairs a casual graphic tank and boot-cut jeans with black open-toe heeled sandals, a quintessential mid-2000s footwear choice that added a dressy touch to her youthful look (Credit: Michael Williams / Startraksphoto)
Back in 2006, long before her red-carpet era with Louis Vuitton, Emma Stone’s early Hollywood style leaned into the mid-2000s uniform of graphic tanks, low-rise denim, and minimalist heeled sandals—an effortless look she wore to Brandon Davis and Replay’s Los Angeles store opening.
17-year-old Emma Stone at the Brandon Davis and Replay celebrate store opening and the launch of The Brandon Davis Jean at Falcon on April 24, 2006, in Los Angeles (Credit: Nikki Nelson / WENN)
Spider-Man 2 Set Style: Purple Ensemble & Stuart Weitzman 5050 Boots
Several years after her 2006 Malcolm in the Middle episode, Emma Stone was back in front of the cameras in March 2013—this time drawing attention on the set of The Amazing Spider-Man 2, where she brightened the day with a chic purple-on-purple ensemble.
Emma Stone wears her blonde hair down on the set of “The Amazing Spider-Man 2” on March 11, 2013, in New York City (Credit: TNYF / WENN)
On the set of The Amazing Spider-Man 2, The House Bunny star wore a polka-dotted button-down top paired with a matching purple skirt with pleats at the hem.
And with those thigh-high boots and tights, she looked like she was modeling for a ready-to-wear collection instead of shooting a scene.
Emma Stone pairs her Cynthia Rowley “Shadow Dots” blouse in Berry and pleated purple skirt with patterned tights and the iconic Stuart Weitzman over-the-knee “5050” boots, creating a sleek, coordinated look on the Amazing Spider-Man 2 set (Credit: TNYF / WENN)
Emma sported a pair of Stuart Weitzman over-the-knee “5050” boots—an iconic flat OTK style known for its half-and-half leather-and-stretch construction that delivers a sleek, second-skin fit.
Another celebrity fan is Alessandra Ambrosio, who wore sleek Stuart Weitzman 5050 over-the-knee leather boots with an all-black ensemble at LAX.
Stuart Weitzman ‘5050’ Over the Knee Leather Boots, $286.07 – $655.00
From Teen Roles to Red Carpet: The Evolution of Emma Stone’s Heel Game
Although her appearance on Malcolm in the Middle shows her still in the early stages of her Hollywood journey—complete with mid-2000s clogs and teen-drama styling—Emma Stone’s fashion sensibility has evolved dramatically since then.
Today, she’s known for sleek Louis Vuitton gowns, refined silhouettes, and a curated rotation of designer heels that consistently highlight her effortless glamour.
✨ Explore Emma Stone’s Best Shoe & Fashion Moments:
- 📏 Standing at 5’6″ (167.6 cm) and wearing a US shoe size 8, the actress frequently chooses Louis Vuitton and Christian Louboutin to elongate her frame.
- 🎬 Her Bugonia Press Tour looks included vintage Donna Karan paired with sleek Manolo Blahnik “Susa” mules.
- 🌊 At the Venice Film Festival, she mastered red-carpet minimalism in a Louis Vuitton black halter dress and Manolo Blahnik “Leva” sandals.
- 🏆 A memorable 2024 Oscar moment saw her complementing her Vanity Fair Oscar Party silver gown with metallic strappy heels.
- 👠 For daytime chic, she styled a Khaite sweater and lace skirt with espresso-brown mesh Aquazzura “Love Affair” pumps.
A year after her mint-green LV moment at the 96th Oscars, Emma returned to the Academy Awards in 2025 with a completely different kind of glamour—sleeker, shimmering, and unmistakably modern.
Emma Stone glowed in a custom champagne sequined Louis Vuitton column gown paired with strappy ivory sandals as she took the stage at the 97th Oscars on March 2, 2025 (Credit: Phil McCarten / The Academy)