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.