5 Fashionable Celebrities Who Took Style Risks: Unexpected Moments

Back in November 2021, designer Tom Ford told GQ magazine he misses the time when celebrities took bigger style risks. “I wish they were a little less powerful, I have to say. There was a time in the seventies, for example, if you look at old Oscar pictures before celebrities had stylists, and my God, people took even more risks. There were great things going down the red carpet then. I think sometimes there becomes a little bit of homogenization, because it isn’t even the stylist.”

Homogenization refers to the process of being similar or uniform. Have celebrities become homogenized in their fashion? The former creative director of Gucci and Yves Saint Laurent says yes. But then you see celebrities like Lady Gaga, Rihanna, and yes, even Kim Kardashian, and you think, no that can’t be. There are still unexpected moments, right? Not like in the past, according to Tom. 

5 Celebrities Who Took Style Risks

So when a celebrity actually tries to take a risk – or wears something super out-of-the-box – is that a good thing? Or are they trying too hard? Let’s weigh in on these five fashionable celebs who have taken major risks with their style in the past few months. Does it work? 


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(No, this isn’t some Worst Dressed list – although at first glance, maybe it should be? The looks are pretty out-there. But that’s what makes them unexpected, right?)

Celebrities Who Took Style Risks Tracee Ellis Ross

Tracee Ellis Ross

Tracee Ellis Ross has been my fashion inspiration for a long time. She’s definitely an MVP of celebrity style, as seen through her many stylish looks — a sleek, red Bottega Veneta turtleneck dress in 2021, the sexy yet sculptural purple padded shoulder Christopher John Rogers dress in 2020, even the glittering gold trench at The Hollywood Reporter & SAG-AFTRA Nominees Night in 2018. 

Not sure what happened in 2022. Tracee has never been one to shy away from color, or risk-taking attire but this year, her fashion seems to have exploded all over the place. Case in point: Those red pasties that were part of that Carolina Herrera gown she wore to the 2022 Oscars. And then, there’s this strange Flintstone-esque dress with a slit at the Black-ish series finale event. The dress is Bottega Veneta, one of Tracee’s go-to designers, so I’m not sure who to blame here. Do I blame her for picking this dress? Or her stylist? Or Bottega Veneta, the label itself, for coming up with this lizard print? I’m not so sure. I see a trend that is teetering towards the extreme for Tracee – more feathers and fur, more color and more strange prints. But to each his own, I guess?

P.S. The blue eye shadow has got to go. 


Julia Roberts

Julia, Julia, Julia. What is going on here? It’s great to see this A-lister actress back on the red carpet, but what’s with the too-short trousers and Oxford booties? Somehow, I like the powdered yellow color of the matchy-matchy suit, but would you rock this look? Julia Roberts can pull it off, but who else? 

Kudos to Julia for presenting a super streamlined and tailored look. But the Lafayette 148 New York suit is too experimental for my taste. At least she didn’t wear matching yellow shoes…

claire foy Celebrities Who Took Style Risks

Claire Foy

Claire Foy, the British actress from the new TV series, ‘A Very British Scandal’, wore a Valentino ensemble to ‘The Late Show With Stephen Colbert’ while promoting the new show. More than that, though, she wore a very recognizable Valentino look, in the form of a dragon print that was first presented in an haute couture gown in 1969. 

Ia this a new take on an old favorite? Maybe. She certainly isn’t the first person who has worn the print in the last few years. 

I think what makes the look so risky, for me, is that it’s not what I think of when I think of Valentino. Maybe you’d disagree with me but I’m used to the Valentino that has structured cuts, streamlined silhouettes, and lots of delicate, romantic and feminine looks. This is certainly not that. 

In any case, whether this look has been reissued again or not, it certainly remains unexpected. As it did in 1969. 

elizabeth olsen Celebrities Who Took Style Risks

Elizabeth Olsen

Elizabeth Olsen has certainly stepped out of the shadow of her twin sisters, and that’s obvious just by the sheer fact that almost never wears black. Of course, this look is not what I’ve come to expect from Ms. Olsen, who certainly takes risks with her fashion, but never as over-the-top as this. 

In fact, I remember seeing her in a lot of minimalist looks; this is quite a departure from that. The sky blue color on this Armani Prive look is lovely, if not a bit much. And of course, who can shy away from that blingy bralette or the embellishments on the shortened wide-leg trousers of that silk suit. 

No, I’m not sure about how I feel about this at all — but she certainly gave me something to chew on. 

daisy edgar jones black gucci dress

Daisy Edgar-Jones

It’s the little things. Like the cone bra on this Gucci dress. And the faux fur trim at the bottom, of course. Talk about adding a bit of edge. That’s exactly what it means to take risks and build unexpected moments with your fashion. That’s exactly what Daisy Edgar-Jones (and Gucci) did here. And I’m here for it. 

– Simona Shemer 

Photos: Red Carpet Fashion Awards 

You may also like to read more of Simona’s celebrity style posts like Oscars 2022 Red Carpet Fashion: The Good, The Mermaids and The Ugly and The Best, The Worst and The Most Boring Met Gala 2021 Fashion.

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