Best Timeless Beauty From Hollywood Legends at the Oscars

The 98th annual Academy Awards are scheduled to take place on Sunday at the Dolby Theatre in Los Angeles, where there will undoubtedly be a healthy serving of smoky eyes, red lips, no makeup-makeup and 1950s-inspired coiffed bobs on the carpet. As the 2026 ceremony nears, WWD is rounding up red carpet beauty that will withstand the test of time, from film legend Jane Fonda to Hollywood starlet Pamela Anderson.

Jane Fonda – 1982

Accepting the award for Best Actor on behalf of her father, Jane Fonda graced the 54th annual Oscars stage with a feathered shag. Her chocolate brown layers swallowed her head like a helmet; the ends just barely brushing her bare collarbone.

Diana Ross – 1985

For her performance at the 57th Academy Awards, Diana Ross donned her signature free-flowing, frizzy ringlets with bouts of coral-toned blush. Meanwhile, her eyes were painted in deep sunset hues, and her lips were dressed in a rose-colored shine.

Shirley MacLaine – 1987

A long-time fan of the square-cut pixie, Shirley MacLaine stayed true to her idiosyncratic style at the 59th annual Oscars, matching her hair, a fiery ginger shade, to the rich red hue of her lipstick.

Liza Minnelli – 1988

Long before Lisa Rinna became the poster girl for a flippy pixie, Liza Minnelli attended the 60th annual Academy Awards with short, finely cut layers framing her face. The “Cabaret” actress posed on the carpet before the ceremony; her wispy bangs tickling the tops of her brows over her long, spider-like lashes.

Helen Mirren – 1995

Helen Mirren attended the 67th annual Academy Awards, where she was nominated for her role as Queen Charlotte in “The Madness of King George.” To honor her first Oscar nomination, the actress opted for a minimal makeup look and a Louise Brooks-esque bob.

Barbra Streisand – 1997

At the 69th annual Academy Awards, Barbra Streisand styled her muddy blond hair in a straight, long-form bob with thin bangs. Her eyes were accentuated with her classic winged liner and charcoal shadow, while her lips were subtly dressed in a pink gloss.

Kathy Bates – 1998

Kathy Bates arrived at the 70th annual Oscars with a ’90s-inspired updo. Her silver layers were pinned and swept away from her face, where she donned ruby red lipstick and light shadow on her eyes.

Meryl Streep – 2006

Meryl Streep brushed her butter blond hair off her face and into a bun for the 78th annual Academy Awards. Dressed in a plum-colored gown, the “Devil Wears Prada” actress strolled across the red carpet with an even-toned complexion and a smile on her face.

Lisa Bonet – 2019

Working with makeup artist Jo Baker, Lisa Bonet matched her glam to her purple sequin mermaid gown, donning pink shimmer on her lids, cat-eye liner, and rose gloss on her lips. Her hair, a mix of braids and dreads, was pulled into an effortless updo.

Pamela Anderson – 2024

After the 2024 Academy Awards, Pamela Anderson arrived at the Vanity Fair Oscars After Party makeup-free. The bare-faced aesthetic wasn’t unusual for the “Baywatch” star, who announced her retirement from heavy glam in a bid to embrace her natural features.