The Best Over-40 Looks on the Grammys Red Carpet

Classic glamour, modern confidence.

Tatiana Bido
Tatiana Bido
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Published: Feb 1, 2026

over 40 grammys — Brianna Bryson/WireImage)/ Getty Images

The Grammys may be known for launching the next wave of breakout artists, but the most compelling beauty moments at the 68th Annual Grammy Awards came from the over-40 crowd. From fearless fashion to classic beauty moments, these stars reminded us that confidence only sharpens with time.

1 / 9

Heidi Klum

The model-TV host-presenter let her plastic sculptural statement dress speak for itself with clean, unfussy beauty. The star wore her long blond hair loose and minimal makeup to keep the focus on her glowing skin.

2 / 9

Ali Wong

Wong went full glam with a 1960s-inspired half-up hairstyle created by celebrity hairstylist Clayton Hawkins. Big volume, height at the crown and a glossy finish delivered old-school glamour, while her makeup stayed classic and polished to balance the bold hair moment.

3 / 9

Gayle King

The TV personality and journalist looked statuesque in her golden gown, pairing it with soft makeup, great skin and a smooth, soft layered bob.

4 / 9

Sharon Osbourne

Taking to the red carpet in her signature red bob, Osbourne kept her makeup refined, pairing soft definition with a black gown and Ozzy-inspired sunglasses.

5 / 9

Queen Latifah

Queen Latifah marked a major beauty moment with a sleek, blunt bob and deep side part. The sharp cut framed her face, drawing attention to radiant skin, sculpted makeup and bold gold accessories paired with her tuxedo-inspired gown.

6 / 9

Nikki Glaser

Skin-first glam took center stage, with a softly sculpted jawline achieved through pre–red carpet prep by facialist Lord Gavin McLeod-Valentine using Augustinus Bader products. An illuminated complexion and strong cat-eye completed the look.

7 / 9

Jennifer Hudson

Jennifer Hudson balanced edge and elegance with a slicked-back bun and smoky eye. Her pulled-back hair emphasized her features, while the makeup delivered depth and drama.

8 / 9

Chaka Khan

The Lifetime Achievement Award winner brought iconic glamour with voluminous hair and confident makeup to the red carpet. The legendary singer delivered a bold, unmistakable Chaka beauty moment.