Why more celebrities need to take beauty risks on the Oscars red carpet

Cher, 1986

Cher showed up at the 1986 Oscars wearing one of the most memorable looks of all time: arched brows, shimmery purple eye shadow, lip gloss. Oh, and a massive headpiece adorned with feathers and rhinestones that gave her a faux widow’s peak.

Juliette Lewis, 1992

Juliette Lewis wore cornrows on her head and Brad Pitt on her arm at the 1992 Oscars. Never forget.

Winona Ryder, 1996

One beauty risk that really paid off in the best way was Winona Ryder’s 1920s-style waves at the 1996 Oscars: an old-fashioned look, but one that looked romantic and flattering on Ryder.

Drew Barrymore, 1998

With brown lipstick and daisies in her hair, Drew Barrymore was the epitome of ‘90s beauty at the 1998 Oscars.

Angelina Jolie, 2000

Angelina Jolie always looks perfectly coiffed and made-up these days, but at the 2000 Oscars she embraced the dark side with a rather goth look involving dramatic eyeliner and long black hair reminiscent of Morticia Adams.

Kate Hudson, 2001

As cute as her curly hair and pastel makeup was at the 2001 Oscars, you have to admit that Kate Hudson has gotten much better at choosing more stylish beauty looks in recent years. Still, it was great to see her embracing her natural curls.

Jennifer Lopez, 2002

Speaking of curly hair… J. Lo stepped out on the red carpet at the 2002 Oscars with some of the biggest hair the world has ever seen.

Beyonce, 2005

At the 2005 Oscars, Beyonce deviated from the norm (and looked amazing doing it) with a double-winged cat-eye and a half-up, half-down hairstyle with plenty of height on top and tousled waves on the bottom.

Michelle Williams, 2006

Everyone remembers this yellow dress at the 2006 Oscars, but it wouldn’t have been half as memorable if Michelle Williams hadn’t paired it with striking red lipstick.

Tilda Swinton, 2008

The most striking part of Tilda Swinton’s beauty look at the 2008 Oscars was that she didn’t really have one, opting to keep her cropped hair swept back and her makeup so minimal that it’s hard to tell if she was wearing any at all.

Sarah Jessica Parker, 2009

While some might have paired a princess gown like hers with an elegant chignon, SJP embraced her hair’s natural volume and wowed with huge, bouncy curls at the 2009 Oscars.

Charlize Theron, 2010

Not many celebrities choose a bold lip color for the Oscars, especially when they’re already wearing a brightly hued dress, but Charlize Theron paired her lilac dress with a bold orange-red lipstick at the 2010 Oscars.

Sandra Bullock, 2010

2010 was apparently a big year for colorful lipstick, since Sandra Bullock also showed up to the Oscars that year with a punchy lip. She decided to use hot pink lipstick to liven up a neutral metallic dress.

Scarlett Johannson, 2011

If bold lipstick is rare on the red carpet, colourful eyeshadow is even more so. Scarlett Johansson somehow managed to pull of vivid orange eyeshadow paired with a magenta dress at the 2011 Oscars.

Reese Witherspoon, 2011

Not many women would choose to wear their hair in a ponytail to the Oscars, but in 2011 Reese Witherspoon did just that–and looked incredibly elegant and gorgeous doing so.

Viola Davis, 2012

Viola Davis wowed at the 2012 Oscars when she showcased her natural, short-cropped hair and matched her eyeliner to her green dress and earrings.

Rooney Mara, 2012

Rooney Mara always has a unique look, but at the 2012 Oscars she really stood out with blunt baby bangs, a high bun, bold brows, and bright red lipstick.

Kerry Washington, 2014

Noticeably pregnant at the 2014 Oscars, Kerry Washington could have gotten away with the bare minimum but instead she wore an attention-grabbing plum lipstick that went surprisingly well with her romantic waves.

Lupita Nyong’o, 2014

At the 2014 Oscars, Lupita Nyong’o showed off her short hair’s natural texture along with a shaved undercut and a delicate gold headband for a beauty look that was both classic and modern.

Zendaya, 2015

Many stars stood out on the red carpet at the 2015 Oscars for their bold hair (Lady Gaga, Scarlett Johansson, and Solange all had interesting hairstyles) but Zendaya garnered the most attention for her dreadlocks–both positive and negative attention (lest we forget Giuliana Ransic’s comments). In the end, this is already an iconic look not only for the controversy it caused but also because, quite simply, it looked amazing on her.