Compared to other awards shows like the Grammys and the VMAs, the Oscars red carpet is a relatively conservative, straight-laced affair. If you were to google “Oscars beauty looks,” you’d see a screen full of pretty much the same thing repeated over and over: gently smoked-out eyeshadow, nude lipstick (with a few classic reds thrown in), and elegant, loose waves. As lovely and timeless as that sort of beauty look is, it does tend to get rather boring after a while. That’s why we’re grateful for the few adventurous souls who decide to bring something unexpected to the Oscars when it comes to their hair and makeup. It’s easy to wear a bold, colourful dress; it’s not that easy to be willing to take a risk with your face or hair.
Still, a few stars took memorable beauty risks over the decades. Some paid off while others tanked, but they all succeeded in the sense that we’re still talking about them today. Perhaps some of these looks will inspire you to start taking more risks with your hair and makeup this year. And as for the trends that haven’t stood the test of time very well (or weren’t particularly flattering even in the year that they were debuted), try to keep in mind all of your own beauty faux-pas before you judge too harshly.
Most of all, let’s have a round of applause for every woman on this list for daring to have some fun with beauty. After all, whether you’re on the red carpet or walking down the street, it’s just makeup and it’s supposed to be fun. It’s a great time to be a beauty lover because it has become more and more acceptable for women to experiment with bold makeup looks and make a statement with one’s hairstyle–just look at Lady Gaga and Zendaya. It’s women like that who will be remembered years later for the beauty risk that they took, instead of all the other attendees who looked the same with their hair and makeup in the usual tasteful but dull Hollywood glam mode.
Here’s hoping that we get to see even more beauty risk-taking at the 2016 Oscars on Sunday night–and in the meantime, enjoy these looks from the past.
Photography by Hulton Archive/Getty Images
Photography by Kypros/Getty Images
Photography by Barry King/WireImage
Photography by S. Granitz/WireImage
Photography by David McNew/Getty Images
Photography by Kevin Winter/Getty Images
Photography by Frank Micelotta/ImageDirect
Photography by Vince Bucci/Getty Images
Photography by Frazer Harrison/Getty Images
Photography by Jeff Vespa/WireImage
Photography by Frazer Harrison/Getty Images
Photography by Steve Granitz/WireImage
Photography by Jason Merritt/Getty Images
Photography by Steve Granitz/WireImage
Photography by Lester Cohen / Getty
Photography by Kevork Djansezian/Getty Images
Photography by Steve Granitz/WireImage
Photography by Jason Merritt/Getty Images
Photography by Jason Merritt/Getty Images
Photography by Steve Granitz/WireImage
1/20
oscars beauty risks 01
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.
2/20
Juliette Lewis
Juliette Lewis, 1992
Juliette Lewis wore cornrows on her head and Brad Pitt on her arm at the 1992 Oscars. Never forget.
3/20
oscars beauty risks 03
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.
4/20
oscars beauty risks 04
Drew Barrymore, 1998
With brown lipstick and daisies in her hair, Drew Barrymore was the epitome of ‘90s beauty at the 1998 Oscars.
5/20
oscars beauty risks 05
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.
6/20
oscars beauty risks 06
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.
7/20
oscars beauty risks 17
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.
8/20
oscars beauty risks 07
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.
9/20
oscars beauty risks 08
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.
10/20
oscars beauty risks 09
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.
11/20
oscars beauty risks 10
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.
12/20
oscars beauty risks 11
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.
13/20
oscars beauty risks 12
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.
14/20
oscars beauty risks 14
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.
15/20
oscars beauty risks 13
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.
16/20
oscars beauty risks 16
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.
17/20
oscars beauty risks 15
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.
18/20
oscars-beauty-looks-kerry-washington
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.
19/20
oscars-beauty-looks-lupita-nyongo
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.
20/20
oscars-beauty-looks-zendaya
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.
![](http://www.facebook.com/sharer.php?u=https://fashionmagazine.com/beauty-grooming/beauty-risks-oscars/&title=Why more celebrities need to take beauty risks on the Oscars red carpet&picture=https://fashionmagazine.com/wp-content/uploads/2016/02/oscars-beauty-risks-05-800x1200.jpg&description=[gallerylink slide="oscars-beauty-risks-01" title="See our fave Oscars beauty looks of all time"]
Compared to other awards shows like the Grammys and the VMAs, the Oscars red carpet is a relatively conservative, straight-laced affair. If you were to google “Oscars beauty looks,” you’d see a screen full of pretty much the same thing repeated over and over: gently smoked-out eyeshadow, nude lipstick (with a few classic reds thrown in), and elegant, loose waves. As lovely and timeless as that sort of beauty look is, it does tend to get rather boring after a while. That’s why we’re grateful for the few adventurous souls who decide to bring something unexpected to the Oscars when it comes to their hair and makeup. It’s easy to wear a bold, colourful dress; it’s not that easy to be willing to take a risk with your face or hair.
Still, a few stars took memorable beauty risks over the decades. Some paid off while others tanked, but they all succeeded in the sense that we’re still talking about them today. Perhaps some of these looks will inspire you to start taking more risks with your hair and makeup this year. And as for the trends that haven’t stood the test of time very well (or weren’t particularly flattering even in the year that they were debuted), try to keep in mind all of your own beauty faux-pas before you judge too harshly.
Most of all, let’s have a round of applause for every woman on this list for daring to have some fun with beauty. After all, whether you’re on the red carpet or walking down the street, it’s just makeup and it’s supposed to be fun. It’s a great time to be a beauty lover because it has become more and more acceptable for women to experiment with bold makeup looks and make a statement with one’s hairstyle--just look at Lady Gaga and Zendaya. It’s women like that who will be remembered years later for the beauty risk that they took, instead of all the other attendees who looked the same with their hair and makeup in the usual tasteful but dull Hollywood glam mode.
Here’s hoping that we get to see even more beauty risk-taking at the 2016 Oscars on Sunday night--and in the meantime, enjoy these looks from the past.
[gallery columns="5" ids="253819,253820,253821,253822,253823,253824,253835,253825,253826,253827,253828,253829,253830,253832,253831,253834,253833,253837,253838,253839"]){kind=link}