Home • News Hairstyle File: Oprah's Best 'Dos Hairstyle File: Oprah's Best 'Dos By Essence · Updated October 29, 2020 01 1986: Cool Crop At the 43rd Annual Golden Globe Awards, Oprah rocked a cool short cut with fluffy bangs. 02 1988: Eighties Elegance At the Emmy Awards, Oprah sported a teased-and-sprayed ’do with loads of bouncy layers and shine. 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. 04 1998: Sultry Upsweep Oprah sported an elegant bouffant upsweep at the 25th Annual Daytime Emmy Awards. 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. 06 2004: Messy Curls Oprah attended a charity event in soft spiral curls and peek-a-boo face-framing ringlets. 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. 08 2005: Glossy Finish Oprah turns on the shine and rocks dramatic makeup at the Broadway opening of The Color Purple. 09 2005: Golden Goddess Oprah was a bronze beauty in these sassy short curls and glowing skin at the Academy Awards. Article continues after video. 10 2006: Curly Updo Oprah wore her curls pulled back in a classy updo at the inauguration of the Hearst Tower. 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. 12 2007: Va-Va-Volume Oprah added golden, honey blonde highlights to her lush tresses when she attended the CDFA Fashion Awards. Shopbop JW Anderson Rectangle Sunglasses SHOP NOW Top Product. Net-A-Porter Miu Miu Tortoiseshell Acetate Sunglasses SHOP NOW Nordstrom Gucci Oval Sunglasses SHOP NOW Bohten Bohten Manyara Chalbi Sun SHOP NOW Coco & Breezy Coco & Breezy Flower SHOP NOW Chimi Chimi The Colton SHOP NOW Akila Akila Polaris SHOP NOW Jimmy Fairly Jimmy Fairly The Emmy SHOP NOW 13 2007: Sweet Curls For the premiere of The Great Debaters, Oprah opted for her signature chunky spirals. 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. 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. Read More Culture Shelly-Ann Fraser-Pryce Brings Her Champion Mindset To Beaut... Fashion Seasoned Black Models Share Their Journeys To Success Lifestyle The Black Girl's Guide To Travel: The Ultimate Women-Only Es... Videos WATCH | Susan L. Taylor’s Annual Gala is Changing Live... Shop These Black-Owned Body Care Brands Will Transform Your Self-...