Olivia Wilde’s High-Heel Evolution: From ‘House’ to the 2020 Critics’ Choice Awards

While Olivia Wilde’s directorial career reached a new peak with Don’t Worry Darling in 2022, her evolution from House breakout to filmmaker has long been charted through her footwear choices.

Standing 5’7″ (170.2 cm), Wilde has consistently leaned on high heels and platforms to sharpen her red-carpet proportions—often selecting leg-lengthening silhouettes that brought her closer in height to then-partner Jason Sudeikis, who stands 6 ft (182.9 cm). Rather than overpowering her look, these choices reinforced her preference for balance, structure, and confident scale.

For more than a decade, the red carpet has served as a testing ground for Wilde’s evolving aesthetic, where ethereal gowns are anchored by architectural heels and statement platforms. From punk-leaning Met Gala moments to polished award-season glamour, her shoes do more than finish an outfit—they quietly shape the visual language of her most defining career eras.

Olivia Wilde, wearing a custom Calvin Klein Collection ivory matte satin bandeau dress with black pleats, heels, and clutch with Fred Leighton jewelry, and Jason Sudeikis attend the Costume Institute Gala for the “PUNK: Chaos to Couture” exhibition at the Metropolitan Museum of Art on May 6, 2013, in New York City (Credit: Bill Davila / Startraksphoto)

Olivia Wilde stepped onto the 2015 Met Gala red carpet in a pink, crystal-embroidered Prada gown, finishing the look with sleek platform heels and Solange Azagury-Partridge earrings, alongside Jason Sudeikis in a sharp white Prada tuxedo on May 4, 2015, in New York City (Credit: Gerardo Somoza / Startraksphoto)

Olivia Wilde, wearing a fluid Alice + Olivia suit styled with classic black ballet flats, a Lidia May Pema top-handle bag, and Foundrae jewelry, arrives alongside Jason Sudeikis at the 9th Annual Veuve Clicquot Polo Classic Los Angeles at Will Rogers State Historic Park on October 6, 2018, in Pacific Palisades, California (Credit: Sara De Boer / Startraksphoto)

One of the most pivotal moments in her fashion evolution occurred in January 2020, when Olivia Wilde joined her longtime partner, Jason Sudeikis, at the 2020 Critics’ Choice Awards.

While the event marked a high point in their public life together, it also served as a definitive showcase of Wilde’s ability to anchor a bold, monochromatic look with high-impact footwear.

Olivia Wilde and then-fiancé Jason Sudeikis attend the 25th Annual Critics’ Choice Awards at Barker Hangar on January 12, 2020, in Santa Monica, California (Credit: Adriana M. Barraza / WENN)

Known for her role as Remy “Thirteen” Hadley on the medical drama series House, the New York City native arrived as a burgeoning director.

Her American coming-of-age comedy film, Booksmart, was nominated for Best Comedy, and her wardrobe reflected that “leading lady” confidence.

She donned a plunging orange Valentino Spring 2020 dress and accessorized with Messika “Mono Boucle Solena Maya” earrings.

Olivia Wilde rocked a plunging orange Valentino dress and Messika jewelry (Credit: Adriana M. Barraza / WENN)

However, the focal point for footwear enthusiasts was her choice of sandals. She showed off her feet in Jimmy Choo “Thyra” sandals, featuring a knotted crystal-encrusted embellishment that provided a sharp, sparkling contrast to the vibrant orange fabric.

Olivia Wilde’s feet in Jimmy Choo’s Thyra sandals with knotted crystal-encrusted embellishment (Credit: Adriana M. Barraza / WENN)

It’s a silhouette that has quickly earned red-carpet status, with its jewel-like finish and leg-lengthening profile making it a favorite among celebrities seeking understated glamour with maximum impact.

Among its high-profile admirers, Kate Beckinsale stepped out in Jimmy Choo’s crystal-embellished Thyra sandals, letting the sparkling heels elevate her bold orange gown and anchor her look with unmistakable evening polish.

Similarly, Kerry Washington embraced the rhinestone-adorned Jimmy Choo Thyra heels at the NAACP Image Awards, proving the design’s versatility as both a statement piece and a refined finishing touch.

Black suede ankle-strap sandals are elevated with a sculptural knotted toe detail encrusted in shimmering crystals for a sleek evening finish

A bold red suede iteration brings drama to the silhouette, pairing slender ankle straps with a sparkling crystal-knot accent across the toes

The metallic version offers a high-glam take, featuring a rhinestone-covered heel and matching crystal embellishment for maximum light-catching impact

Stepping Through Olivia Wilde’s Most Defining Shoe Moments

While headlines have often followed Olivia Wilde off the red carpet, it’s her footwear choices that quietly anchor her most memorable fashion eras.

From early-career appearances to recent directorial-era looks, these curated moments highlight how shoes have remained central to her evolving style story.