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Home • News

Hairstyle File: Oprah's Best 'Dos

Hairstyle File: Oprah's Best 'Dos
By Essence · Updated October 29, 2020
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01
1986: Cool Crop

At the 43rd Annual Golden Globe Awards, Oprah rocked a cool short cut with fluffy bangs.

Hairstyle File: Oprah's Best 'Dos
02
1988: Eighties Elegance

At the Emmy Awards, Oprah sported a teased-and-sprayed ’do with loads of bouncy layers and shine.

Hairstyle File: Oprah's Best 'Dos
03
1995: Casual Chic

At the ‘Get Movin’ With Oprah’ Spring Training Mother’s Day Walk, Oprah looked casually cool in this breezy short style.

Hairstyle File: Oprah's Best 'Dos
04
1998: Sultry Upsweep

Oprah sported an elegant bouffant upsweep at the 25th Annual Daytime Emmy Awards.

Hairstyle File: Oprah's Best 'Dos
05
2002: Face-Framing Layers

Oprah was all smiles in soft, face-framing layers and a chic, eyebrow-grazing bang.  A bold red lip adds extra wow-factor to this look.

Hairstyle File: Oprah's Best 'Dos
06
2004: Messy Curls

Oprah attended a charity event in soft spiral curls and peek-a-boo face-framing ringlets.

Hairstyle File: Oprah's Best 'Dos
07
2004: Short & Sweet

Oprah stepped out at the Academy Awards in a short layered shag, which became one of her most memorable haircuts during her career.

Hairstyle File: Oprah's Best 'Dos
08
2005: Glossy Finish

Oprah turns on the shine and rocks dramatic makeup at the Broadway opening of The Color Purple.

Hairstyle File: Oprah's Best 'Dos
09
2005: Golden Goddess

Oprah was a bronze beauty in these sassy short curls and glowing skin at the Academy Awards.

Hairstyle File: Oprah's Best 'Dos
10
2006: Curly Updo

Oprah wore her curls pulled back in a classy updo at the inauguration of the Hearst Tower.

Hairstyle File: Oprah's Best 'Dos
11
2006: Stylish Flip

The media mogul wore her hair with the ends flipped and lots of volume when she arrived at her much-talked-about Legend’s Ball.

Hairstyle File: Oprah's Best 'Dos
12
2007: Va-Va-Volume

Oprah added golden, honey blonde highlights to her lush tresses when she attended the CDFA Fashion Awards.

Hairstyle File: Oprah's Best 'Dos
13
2007: Sweet Curls

For the premiere of The Great Debaters, Oprah opted for her signature chunky spirals.

Hairstyle File: Oprah's Best 'Dos
14
2008: Full Spirals

At a charity fundraiser, all eyes were on Oprah as she walked the red carpet in a halo of cascading curls.

Hairstyle File: Oprah's Best 'Dos
15
2011: Pretty Pony

At an OWN cocktail party, Oprah turned heads in this sophisticated and sleek ponytail with a hint of volume in the crown.

Hairstyle File: Oprah's Best 'Dos