Whether she’s commanding the spotlight during Academy Awards weekend or embracing the playful energy of the Teen Choice Awards, Ashley Benson consistently uses statement heels to sharpen her red-carpet presence.
In this style recap, we revisit three standout moments across different years: a mirror-embellished Alevì Milano sandal paired with a high-shine Hervé Léger gown in 2022, metallic Manolo Blahnik strappy heels elevating couture mini glamour that same Oscar weekend, and a throwback Teen Choice Awards look where Michael Kors “Jacqueline” sandals replaced the fluffy flip-flops she wished she could wear.
Each outfit highlights a different chapter of Benson’s evolving aesthetic — from architectural shine to sleek metallic minimalism to youthful red-carpet polish — all anchored by carefully chosen footwear.
Architectural Shine: Alevì Milano “Penelope” Sandals at the 2022 Elton John Oscar Party
During the 30th Annual Academy Awards Viewing Party in West Hollywood on March 27, 2022, Benson opted for a high-shine aesthetic.
She paired a daring Hervé Léger Fall 2022 dress with Penelope 100mm sandals from Alevì Milano. The heels, featuring intricate mirror patch appliqués, offered a modern architectural contrast to the classic bandage-style slits of her gown.
Ashley Benson in a Hervé Léger Fall 2022 dress with Alevi Milano Penelope heels and Yeprem jewelry at the Elton John AIDS Foundation’s 30th Annual Academy Awards Viewing Party on March 27, 2022, in West Hollywood, California (Credit: Fayes Vision / Startraksphoto)
Metallic Glamour: Manolo Blahnik “Bayan” Sandals With Tony Ward Couture in Bel Air
The night prior, at a pre-Oscars event in Bel Air, she showcased her versatility in a gold Tony Ward Couture mini dress.
She elevated the metallic look with Manolo Blahnik sandals, specifically the Bayan metallic leather strappy heels, which elongated her frame and complemented the dress’s intricate beadwork.
Actress Ashley Benson in a sheer Tony Ward Couture Spring 2022 mini dress and Manolo Blahnik Bayan metallic leather strappy sandals at the Oscar Party hosted by Darren Dzienciol and Richie Akiva on March 26, 2022, in Bel Air, California (Credit: Xavier Collin / Image Press Agency)
While her 2022 Oscar-weekend appearances showcased a polished, high-shine sophistication, stepping back a few years reveals a slightly more playful chapter in Benson’s red-carpet evolution — one where youthful energy met sleek designer sandals.
Youthful Red-Carpet Edge: Michael Kors “Jacqueline” Sandals at the 2016 Teen Choice Awards
Ashley Benson frames her softly contoured makeup with understated Jennifer Meyer earrings that add a subtle, modern finish (Credit: WENN)
In July 2016, Ashley expressed her desire to stay in a pair of fluffy pink flip-flops on the morning of the 2016 Teen Choice Awards in Los Angeles.
Ashley Benson flaunts her legs in a metallic mini dress by Michael Kors at the 2016 Teen Choice Awards in Los Angeles on July 31, 2016 (Credit: Adriana M. Barraza / FayesVision / WENN)
Unfortunately for Ashley, comfort had to take a back seat to red-carpet glamour. Swapping her fluffy flip-flops for full-on shine, she stepped out in a head-to-toe Michael Kors ensemble anchored by a sleek silver dress that caught the light from every angle.
Ashley Benson highlights her crisp white pedicure in metallic silver Michael Kors “Jacqueline” sandals featuring a sleek toe strap and delicate ankle buckle (Credit: WENN)
Her metallic dress was held together by several rings, which reminded us of medieval mail chain armor. The American actress had to give up her fluffy footwear for a pair of Michael Kors “Jacqueline” sandals. Another celebrity fan of these shoes is Hailee Steinfeld, who wore them with a sequined dress at the new Gold Collection fragrance launch hosted by Michael Kors.
Ashley started her Teen Choice glam journey with a facial from Origins before she flew back to Los Angeles in a pair of comfortable sweats.
The aforementioned fluffy footwear made an appearance on her Snapchat with the caption, “wish I could wear these.”
Tyler Blackburn, Ashley Benson, Shay Mitchell, and Troian Bellisario pose with the award for Choice TV Show: Drama for ‘Pretty Little Liars’ in the press room during Teen Choice Awards 2016 at The Forum on July 31, 2016, in Inglewood, California
Ashley Benson’s Shoe Evolution: From Red-Carpet Stilettos to Off-Duty Cool
From architectural Oscar-weekend heels to metallic Teen Choice sandals, Ashley Benson’s style journey proves that footwear remains the foundation of her fashion identity.
Whether she’s embracing sleek designer minimalism, experimenting with playful textures, or leaning into laid-back street style, her shoe choices consistently sharpen the overall look.
For more of her standout heel moments, casual sneaker pairings, and brand-driven red-carpet highlights, explore the curated features below.
- 📏 Ashley Benson’s height & shoe size guide — a footwear-first roundup of the heel brands she repeats and how she uses stilettos, platforms, and sleek pumps to boost her 5’3½” frame.
- ✨ Her futuristic Teen Choice Awards moment in Michael Kors — a head-to-toe silver look finished with matching Michael Kors sandals.
- 🖤 Ashley Benson’s chic PaleyFest suit styled with Jimmy Choo “Minny” sandals — a menswear-leaning Stella McCartney ensemble grounded by minimalist velvet heels.
- 🐄 Her off-duty denim shorts look with Simon Miller cow-print thong sandals — a playful street-style pairing featuring the brand’s sculptural comma heel.
- 🧥 Rocker-chic street style in a Saint Laurent biker jacket — a casual-cool coffee run finished with Adidas Adilette slides.
- 👜 Salon-day casual featuring Dolce & Gabbana’s Miss Sicily satchel — an off-duty snapshot with leopard-print sneakers and laid-back Beverly Hills polish.
- ✂️ Ashley Benson’s blonde hair refresh + ripped-skinny-jeans outfit — a throwback street-style moment spotlighting her casual staples (and another Miss Sicily cameo).