We Went Down a Rabbit Hole of Patrick Dempsey’s Most Iconic ‘80s and '90s Fits

Patrick Dempsey has been a Hollywood staple forever. Can't Buy Me Love. Sweet Home Alabama. And, of course, Grey’s Anatomy’s McDreamy, of which he recently made a surprise return to. Just like that good ole TV character nostalgia, Dempsey also has a penchant for making us miss many ‘90s things—especially the outfits.

Dempsey has always had good style. He has worn suits of every shape, gotten very liberal with what a ‘dress shirt’ means, and even as his style has evolved, the quality has remained.

But style evolution isn’t just about the clothes. It’s about the whole picture. The whole vibe. And Patrick Dempsey has always maintained an extremely Patrick Dempsey vibe, especially visible through his hair evolution. He’s had long and short, curly and spiky, fully exposed bedhead, and an abundance of hat experiments. An abundance.

Here, we rounded up some of his finest fits, from the young Patrick Dempsey to the 2021 version. Prepare yourself for the many '80s and ‘90s outfits that we can appreciate but also definitely not bring back into rotation.