As someone who studies a lot of celebrity outfits (it’s my job, after all), I find some of the most memorable outfits to be the ones in which the celebrity in question strayed from their typical aesthetic. Think black dress–loving Jennifer Aniston instead wearing a shiny, pink gown to a premiere, or that epic Katie Holmes Khaite cardigan street style moment that practically broke the internet.
Some (like the aforementioned Katie Holmes moment) are more memorable, while others on this list are ones you may not have even seen before. Either way, they’re sure to make you do a double take or two. That said, there are plenty of celebrities whose style is constantly evolving, so when they switch things up, it isn’t all that surprising. Most of the following celebrities have somewhat of a signature style, which makes their outside-the-box outfits even more noteworthy. And in case you’re intrigued by what these stylish celebs are wearing, I found some similar shopping options for your own double take–worthy outfits. Scroll to see what I’m talking about for yourself.
Rihanna constantly keeps us on our toes, but I can’t recall a time that she’s donned such a literal ’80s punk-rock look. But she certainly pulls it off and proves that the checkerboard trend is still as popular as ever. On Rihanna: Raf Simons jacket; Vivienne Westwood True Punk Print T-Shirt ($303); Maximilian pants; Sophia Webster shoes; Versace sunglasses; Prada Printed Twill Scarf ($240)
This is the moment that made Katie Holmes a modern-day street style star. Sure, the outfit as a whole isn’t that far off from what she usually wears, but this was the first time she became a full-blown trendsetter. On Katie Holmes: Khaite Scarlet Cardigan ($1580) and Eda Bralette ($520)
I don’t know about you, but I won’t soon forget Michelle Obama in these epic thigh-high Balenciaga boots. On Michelle Obama: Balenciaga dress and boots; Jennifer Fisher Baby Jamma Hoops ($550)
Kendall Jenner’s aesthetic is usually casual and cool; sometimes androgynous, sometimes athleisure-focused, and sometimes resembling that of a cool club kid from the ’90s. It’s not often that we see her in a pretty, puff-sleeve dress, but this Rodarte number is one she’d be wise to repeat. On Kendall Jenner: Rodarte dress
Amal Clooney’s style is actually fairly eclectic, which makes sense because by day she’s a high-powered attorney, and (sometimes) by night she’s a red carpet regular. But this very ’70s-inspired off-duty look from five years ago is one we’re not used to seeing her in. She clearly pulled it off, though, as she does everything. On Amal Clooney: Alice+Olivia jeans
The bulk of EmRata’s wardrobe appears to consist of crop tops, baggy jeans, oversized blazers, minidresses, and sneakers, so when she stepped out in this flowy, ruffled dress, I almost didn’t realize it was her. On Emily Ratajkowski: Miu Miu dress; Brock Collection boots; Prada bag
If you look back at Jennifer Aniston’s style for the past 20 years or so, it’s clear that she has a signature look. It’s sleek, it’s modern, and it’s usually in black. While the silhouette of this dress is certainly in keeping with her style, the fabric and color are a departure for her. On Jennifer Aniston: Christian Lacroix Couture dress
New mom Gigi Hadid had a new uniform this past winter, often consisting of baggy jeans, boots, a hat, and an oversized coat. The cool, comfortable look suits her well. On Gigi Hadid: Louis Vuitton hat; Thom Browne coat; Dr. Martens boots
It’s a known fact that Kate Middleton adheres to somewhat of a dress code as a member of the royal family, and her outfits are typically very structured and tailored. When she stepped out in this Gucci pussy-bow blouse and relaxed wide-leg pants, it felt like a departure for her, and I was here for it. On Kate Middleton: Gucci top
It goes without saying that Lady Gaga is known for having some wild looks and an ever-evolving signature style. When she was doing press for A Star Is Born, she took on the vibe of a glam movie star. Here’s just one example. On Lady Gaga: Gabriela Hearst coat; Celine bag
Taylor Swift is another celebrity with ever-evolving style (which is often reflective of the album she’s working on). For the SNL after-party in 2019, she donned sparkly wide-leg pants and an oversize blazer. It was quite different for her and very successful. On Taylor Swift: Libertine pants; Christian Louboutin shoes
Zendaya has some of the most eclectic red carpet style in the business, and she always keeps us on our toes. While she often opts for avant-garde looks, for a premiere in 2018, she went with a sweet minidress and white heels—an easy-to-re-create look that would work for many different occasions. On Zendaya: Michael Kors dress; Christian Louboutin shoes
