In March 2019, at the South by Southwest Film Festival in Austin, Texas, Olivia Wilde introduced Booksmart to the world—marking a confident directorial debut that quickly became one of the most talked-about films of its year.
The coming-of-age comedy, centered on two overachieving best friends determined to reclaim lost time on the eve of graduation, struck a rare balance between sharp humor and emotional honesty.
Katie Silberman, Olivia Wilde, Beanie Feldstein, Kaitlyn Dever, and Billie Lourd showcase their distinct styles at the 2019 SXSW Film Festival, pairing elegant dresses with chic footwear—from heeled sandals to statement boots—on March 9, 2019 (Credit: Nicky Nelson / Lu Chau / WENN)
As Booksmart moved from festival buzz to awards-season conversations, its success also created a series of fashion moments that extended well beyond the screen.
From red-carpet premieres to post-release appearances, Wilde and the film’s cast leaned into thoughtful, expressive styling—where polished silhouettes and carefully chosen footwear played a quiet but defining role in shaping each look.
Critical Acclaim and Award Recognition
The film received widespread critical acclaim, with Rotten Tomatoes ranking Booksmart as the number one comedy of the decade—an achievement that underscored both its sharp writing and standout performances.
At the center of that success was Beanie Feldstein’s portrayal of Molly Davidson, a role that earned her a Golden Globe nomination for Best Actress in a Comedy.
Standing 5ft 1 (154.9 cm) and typically wearing a US shoe size 8, Feldstein brought outsized presence and confidence to the screen, proving that commanding performances have nothing to do with stature. She ultimately lost the award to Awkwafina for The Farewell, but the nomination firmly established her as one of the most compelling comedic actors of her generation.
Beanie Feldstein shines in a sequined floor-length gown cinched with a satin belt at the Los Angeles special screening of Annapurna Pictures’ Booksmart at the Ace Hotel on May 13, 2019
Olivia Wilde’s Fashion Moment at Palm Springs
In January 2020, actress-turned-director Olivia Wilde attended the Palm Springs International Film Festival to discuss her movie.
She showcased her sartorial flair in a summery red dress from Russian fashion designer Ulyana Sergeenko’s Spring/Summer 2019 collection. The vintage-looking summer-ready frock features tiny white flower prints, trendy puff sleeves, a sweetheart neckline, and a belted waist.
Olivia Wilde radiates effortless elegance at the Booksmart Q&A during the 31st Annual Palm Springs International Film Festival, pairing a floral Ulyana Sergeenko dress with striking red Chloe Gosselin slingback pumps on January 3, 2020
Breaking Down Olivia Wilde’s Stunning Look
Thanks to hair and makeup artist Blondie, Olivia looked even more radiant with a dusty rose blush, matching lip gloss, eyeliner, and mascara. She wore her blonde locks in beautiful curls, framing her perfectly made-up face.
Olivia Wilde radiates effortless charm with soft curls, layered gold necklaces, and minimal makeup featuring a dusty rose lip shade and blush, perfectly complementing her floral red dress
Stylist Karla Welch accessorized Olivia’s look with gold jewelry and red slingback Alaide pumps by Chloe Gosselin. Her suede shoes feature pointed toes, thick slingback straps, bamboo buckles, and about 4-inch block heels.
For more footwear inspiration, see how Olivia Wilde styled red Paul Andrew heels with a red-and-white Rosie Assoulin dress.
Olivia Wilde completes her look with bold red Chloe Gosselin ‘Alaide’ slingback pumps featuring pointed toes, bamboo buckle details, and chic suede texture
Olivia Wilde’s striking red Chloe Gosselin ‘Alaide’ slingback pumps perfectly complemented her floral dress, proving that bold footwear can elevate even the most effortless looks.
As a longtime fan of elegant yet modern shoe designs, Wilde joins a growing list of stylish celebrities who have stepped out in Chloe Gosselin’s coveted heels.
Stepping Out in Style: Celebrities Who Love Chloe Gosselin
From Keira Knightley’s ethereal ‘Narcissus’ sandals to Reese Witherspoon’s sophisticated ‘Helix’ pumps, Hollywood’s most fashionable women continue to embrace the brand’s timeless appeal. Let’s take a closer look at some of the most memorable Chloe Gosselin celebrity moments.:
Keira Knightley in ‘Narcissus’ Sandals at the ‘Colette’ Premiere
- Event: ‘Colette’ Premiere at the Samuel Goldwyn Theater
- Outfit: Keira Knightley looked effortlessly glamorous in a light pink silk strapless dress from Chanel’s Haute Couture collection, adorned with feathers and sequins.
- Footwear: She complemented her ensemble with Chloe Gosselin’s ‘Narcissus’ sandals, showcasing her impeccable style.
- More Details: Keira Knightley’s perfect feet in ‘Narcissus’ sandals at ‘Colette’ premiere
Emma Roberts and Reese Witherspoon in ‘Helix’ Pumps
- Events: Toronto International Film Festival and Producers Guild Awards
- Outfits: Emma Roberts stunned in a white shift dress at TIFF, while Reese Witherspoon donned a nude Dolce & Gabbana dress at the PGA.
- Footwear: Both actresses chose Chloe Gosselin’s ‘Helix’ pumps—Emma in black and Reese in rust velvet—highlighting the design’s versatility.
- More Details: Emma Roberts & Reese Witherspoon rock Chloe Gosselin’s ‘Helix’ pumps
Olivia Munn in ‘Enchysia’ Pumps at the CFDA/Vogue Fashion Fund Awards
- Event: 13th Annual CFDA/Vogue Fashion Fund Awards
- Outfit: Olivia Munn turned heads in a black Tanya Taylor slit dress adorned with floral embellishments.
- Footwear: She paired her ensemble with pink suede Chloe Gosselin ‘Enchysia’ pumps, praising their comfort and style.
- More Details: Olivia Munn’s feet in ‘painless’ Chloe Gosselin ‘Enchysia’ pumps
Catherine Zeta-Jones in ‘Tori’ Swarovski Sandals at Wales’ National Day Gala
- Event: 2019 Wales’ National Day Gala
- Outfit: Catherine Zeta-Jones dazzled in an appliquéd velvet gown by Marchesa.
- Footwear: She showcased Chloe Gosselin’s ‘Tori’ Swarovski sandals, adding a touch of sparkle to her ensemble.
- More Details: Catherine Zeta-Jones’ tortured feet in ‘Tori’ Swarovski sandals
Krysten Ritter in ‘Nicole’ Pumps at ‘El Camino’ Premiere
- Event: ‘El Camino: A Breaking Bad Movie’ Premiere
- Outfit: Krysten Ritter made a daring comeback in a Georges Chakra beaded tulle dress.
- Footwear: She completed her look with Chloe Gosselin’s ‘Nicole’ pumps, featuring delicate gold chain-link T-straps.
- More Details: Krysten Ritter looks bewitching in Chloe Gosselin ‘Nicole’ pumps
These moments highlight Chloe Gosselin’s appeal among celebrities, offering designs that range from bold statements to elegant classics.