Jessica Alba’s Style Evolution: From Never Been Kissed Teen Star to Effortlessly Chic CEO

In Never Been Kissed (1999), Jessica Alba starred as Kirsten Liosis, a member of the popular high school clique. While Alba’s role was secondary to Drew Barrymore’s lead character, Josie, her fashion moments in the film still stand out, marking her early Hollywood style.

Alba’s character, Kirsten, often wears stylish, high-school-appropriate outfits that highlight her popular, “cool girl” persona. Her footwear choices are classic for the late ’90s, with trendy heels and platforms that reflect her character’s confident, social status.

Jessica Alba, Marley Shelton, Jordan Ladd, and Drew Barrymore share a carefree moment in Never Been Kissed (1999), capturing their iconic, laid-back summer style as they relax together in casual outfits perfect for the era

Though Alba’s role wasn’t the film’s focus, her character’s fashion choices, including the shoes, subtly contribute to the movie’s themes of confidence, popularity, and the high school experience, adding a stylish layer to the overall fashion narrative.

Jessica Alba, who turned 17 during the filming of Never Been Kissed (1999), attended the Los Angeles premiere in a standout look that perfectly captured the early ’90s vibe.

Jessica Alba stunned at the Never Been Kissed premiere on March 30, 1999, in a chic light blue halter-top ensemble paired with matching wide-leg pants, complemented by strappy sandals—an effortless yet elegant look that showcased her blossoming Hollywood style (Credit: WENN / Marcus Hoffman)

Reflecting on her experience filming the romantic comedy, she shared, “It felt like camp, but you also really took so many people under your wing and guided them. A lot of us were just starting out and you set the stage… and gave us a platform to be successful.”

Alba’s heartfelt gratitude to Drew Barrymore for her mentorship on set highlights the camaraderie they shared, with both actresses at pivotal stages in their careers.

This still from the 1999 movie Never Been Kissed shows Jessica Alba, Jordan Ladd, and Marley Shelton in their vibrant Barbie-themed prom costumes, with Alba in a floral-inspired outfit and strappy sandals, while Ladd and Shelton complete their looks with playful footwear matching their costumes

While Jessica Alba’s Never Been Kissed days showcased her early Hollywood charm and laid-back ’90s style, her fashion evolution continued as she navigated both her acting career and entrepreneurial ventures.

Fast forward to 2016, and Alba’s sense of style had matured, reflecting her status as a business mogul and a mother, all while maintaining a chic, off-duty aesthetic. One such moment that encapsulated her effortless yet stylish approach was her casual airport look in January 2016.

Jessica Alba’s Effortless Airport Style: A Chic 2016 Look

Jessica Alba wears her hair down as she arrives at Los Angeles International Airport on January 2, 2016

On January 2, 2016, Jessica Alba was photographed arriving at Los Angeles International Airport with her daughters and husband, who limped his way on crutches to a waiting car.

Jessica Alba, with her daughters at the airport in 2016, was wearing a casual yet stylish look with white sneakers, relaxed denim, and a cozy cardigan while guiding her children through the arrivals area

Jessica Alba exuded effortless chic at the airport, pairing a Z Supply Pocket Tee in White with The Great. Slouch Armies in True Blue.

She accessorized the look with a sophisticated Chanel Paris-Salzburg Cashmere Flap Bag. Her outfit was completed with Vans Leather Old Skool Zip Sneakers in True White/Gold, showcasing her signature casual yet stylish flair.

Close-up of Jessica Alba’s sneakers, featuring a sleek, white design with a zipper detail, adding a modern touch to her laid-back airport outfit

As the CEO of The Honest Company, Jessica Alba swiftly ushered her daughters into the car, eager to avoid the paparazzi, leaving her injured husband behind.

Despite the setback, Cash Warren remained unfazed, casually revealing that he had torn his Achilles tendon while making his way through the airport on crutches.

Cash Warren at the airport in 2016, navigating through the terminal on crutches after injuring his Achilles tendon, paired with a playful, colorful sweatshirt and stylish sneakers

Wrapping Up Jessica Alba’s Footwear Evolution

As we’ve explored Jessica Alba’s diverse shoe styles—from high heels to casual sneakers—it’s clear that her fashion choices have played a significant role in shaping her public persona.

Whether walking the red carpet or strolling through the airport, Alba’s footwear reflects her effortless style and fashion-forward mindset.