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The Most Daring Dresses Of The Year

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24. Phoebe Waller-Bridge At The 2020 SAG Awards
Phoebe Waller-Bridge had a lot to celebrate when she hit the SAG Awards in a sultry Armani Privé sheer top, bandeau, and black floor-length skirt. The British star won big that night when she was awarded the prize for Best Comedy Actress for her work in Fleabag. 

During her acceptance speech, the actress jokingly gave a shoutout to her makeup artist for drawing on a six-pack underneath her outfit. "With all the chaos of the outfits, and the interviews and the six-pack that my makeup artist drew on me this evening and all the kinds of pre-drinks and after-parties, and all the amazing Hollywood-y things that happen here, it’s quite easy to be distracted from the thing that has actually happened to us." 

Waller-Bridge also spoke to Vogue about her thoughts on dressing herself. “I find dressing really stressful, just that decision every day. You want to just Steve Jobs it. When you land on an outfit that you love, there’s no greater feeling. [But] I maintain the right to leave the house... in my pajamas. I think I felt like the most important thing was how I looked — especially in your 20s, when everyone’s like, ‘Cash in on it now because you haven’t got a lot of time!' Hair was everything. I had to remember how to be free.”