Hailee Steinfeld’s Dreamy Oscars Style Through the Years — From Teen Ingénue to Red-Carpet Royalty

From her tea-length Marchesa debut at 14 to a shimmering Elie Saab fairytale in 2024, Hailee Steinfeld has quietly built one of the Oscars’ most romantic red-carpet style stories. Below, we’re revisiting the gowns, jewels, and heels that chart her evolution from ingénue to certified Hollywood fashion fixture.

To see just how far she’s come, it helps to start at the very beginning—with the fairytale-worthy Oscars debut that introduced Hailee’s dreamy, ultra-feminine red-carpet aesthetic to the world.

A Fairytale Beginning: Hailee Steinfeld’s 2011 Oscars Debut

Looking back at Hailee Steinfeld’s ethereal debut seasons on the Oscars red carpet, it’s remarkable how quickly she evolved from a teenage ingénue into a confident Hollywood style fixture.

Hailee Steinfeld, then 14, exuded youthful elegance in a pale pink custom Marchesa tea-length gown, Ferragamo heels, and vintage Fred Leighton diamonds at the 83rd Annual Academy Awards in 2011 (Credit: Ivan Vejar / ©A.M.P.A.S.)

Six years after her first Academy Awards appearance, the then-20-year-old actress and singer returned to the spotlight for the 89th annual Oscars, exuding the poise of a seasoned pro.

Blooming Elegance: Ralph & Russo Couture at the 2017 Oscars

Joined by fellow fashion standouts Ginnifer Goodwin and Jessica Biel, Hailee floated down the red carpet in a light, dreamy gown that captured the romantic, couture-driven mood of the night. The look signaled her transition from rising star to red-carpet veteran — a defining Oscars moment that still feels timeless years later.

Hailee Steinfeld stuns with a chic updo and smoky eye makeup

Hailee wore a floral gown from Ralph & Russo’s spring 2017 couture collection. The floor-sweeping dress featured a halter neckline, a thin waistband, and ruffled details.

Her gown had a sheer overlay and gorgeous floral appliqués, and was seriously dramatic, with a trail of ruffled flowers running down her back.

Hailee Steinfeld radiates elegance in a sheer Ralph & Russo gown with cascading floral details and a dramatic train at the 2017 Oscars

Minimal Styling for Maximum Impact

Since a lot was going on with her dress, Hailee kept her styling minimal. She swept her hair in a chic updo to highlight her ruffled neckline. Hailee accessorized with diamond studs, a cocktail ring, and a diamond bracelet from Neil Lane.

Finally, she finished her look with smoky eyes, soft pink lips, and heels from Charlotte Olympia. She wore shoes by the same designer at the 2016 Met Gala and the 2015 MTV Video Music Awards.

To replicate Hailee Steinfeld’s Oscars look, opt for a sheer halter gown with floral appliqués, delicate ruffles, and soft, minimal accessories for a timeless red carpet vibe

Charlotte Olympia Footwear: Hailee Steinfeld’s Shoe Designer of Choice

While Hailee Steinfeld’s ethereal Ralph & Russo gown gracefully concealed her footwear at the 2017 Oscars, it’s noteworthy that she has previously showcased Charlotte Olympia’s exquisite designs. For instance, at the 2015 MTV Video Music Awards, Hailee adorned her feet with gold-tone calf leather Octavia sandals, exemplifying her penchant for the brand’s sophisticated aesthetics.

Charlotte Olympia, renowned for its unique and whimsical creations, has been a favorite among celebrities. Lily Aldridge, for example, embraced a playful yet chic look by pairing leopard-print Charlotte Olympia cat-face flats with an all-white ensemble, demonstrating the brand’s versatility.

Hailee’s understated diamond studs, bracelet, and cocktail ring added just the right touch of sparkle to complement her ethereal gown

For readers interested in exploring more about Charlotte Olympia’s iconic designs and their influence in the fashion world, Your Next Shoes offers several insightful articles:

• Discover how Jennifer Lopez styled the blush suede ‘Dolly’ pumps with a form-fitting Houghton dress during a SAG-AFTRA Foundation event.
• Learn about Coco Austin’s bold choice of rainbow-feathered ‘Dolly’ pumps at the ‘Think Like a Man Too’ premiere, showcasing the shoe’s versatility.
• See how Julia Roberts complemented her purple Proenza Schouler dress with matching satin ‘Dolly’ pumps at the ‘August: Osage County’ premiere.

These articles on Your Next Shoes offer a comprehensive look at Charlotte Olympia’s contributions to the fashion industry, providing readers with a deeper appreciation of the brand’s unique style and legacy.

Hailee Steinfeld at the 89th Annual Academy Awards held at the Dolby Theatre at the Hollywood and Highland Center in Los Angeles, California, on February 26, 2017 (Credit: Adriana M. Barraza / WENN / Dave Bedrosian / Future Image / Apega)

Behind the Gown: Hailee’s Oscars Experience & Red Carpet Interview

The “Edge of Seventeen” star also stopped by for an interview with Entertainment Weekly on the red carpet.

She talked about her Ralph & Russo number, the only dress she tried on for the event. In addition, she recalled her first Oscars experience and compared it to her most recent one.

Hailee also shared photos of her getting ready and having a princess moment on the red carpet. Likewise, Ralph & Russo showed Hailee’s “exquisite” look at this year’s Academy Awards.

Revisiting 2017’s Most Iconic Oscars Fashion Moments

The 2017 Oscars showcased a myriad of unforgettable fashion moments. Emma Stone, for instance, embodied old Hollywood glamour in a custom Givenchy Haute Couture gown, a look that contributed to her Best Actress win for “La La Land.”

Similarly, Nicole Kidman turned heads in a nude Armani Privè gown adorned with intricate beading, perfectly complementing her porcelain complexion.

For a deeper dive into the standout styles of the evening, explore our comprehensive coverage of the 2017 Oscars fashion highlights.

Modern-Day Fairytale: Hailee Steinfeld’s 2024 Oscars Return

Thirteen years after her first Academy Awards appearance, Hailee Steinfeld returned to the Oscars red carpet on March 10, 2024, radiating poise and confidence in a look that felt like the natural evolution of her Hollywood story.

Hailee Steinfeld radiated ethereal beauty at the 2024 Oscars in a pastel blue Elie Saab Haute Couture gown adorned with gilded leaf appliqués, styled with Chopard jewels and a sleek updo (Credit: Warrick Page ©A.M.P.A.S.)

The actress and singer embodied modern fairytale glamour in a pastel blue Elie Saab Haute Couture Spring/Summer 2024 gown — a diaphanous creation with pleated chiffon, butterfly sleeves, and gilded leaf appliqués that moved like liquid air as she walked.

Hailee Steinfeld brought fairytale glamour to the 2024 Oscars in a pastel blue Elie Saab Haute Couture gown paired with Jimmy Choo Max sandals and Chopard jewels (Credit: Nick Agro / ©A.M.P.A.S.)

Styled by Rob Zangardi and Mariel Haenn, Hailee completed the ethereal ensemble with shimmering Chopard and Wempe jewels and sky-high Jimmy Choo “Max” platform sandals, balancing delicate femininity with star-level confidence. The look was a testament to her fashion maturity — elegant, effortless, and perfectly timed for her Oscars homecoming.