We Tracked Patrick Dempsey’s Style Evolution From a Young Teen Heartthrob to Dr. McDreamy

Well, young Patrick Dempsey is an absolute icon, as this hair and outfit undoubtedly prove. Dempsey has always had a little fun with his outfits, like mixing patterns.

Technically this photo is from the ‘80s but that hair is quintessential ‘90s. Doesn’t come as a surprise that Dempsey was ahead of the times on good hair moves.

Fast Times wardrobes are the ones we can take some inspiration from and make ‘em modern. Layering fun patterned shirts and cardigans or denim jackets is solid—even better if you thrifted them.

Layering a trucker jacket over a fancier shirt is a cool move for the fashion inclined. Not to mention, these pants are it—then and forever.

When young Patrick Dempsey does formal, he does formal. This perfectly fitted tux and styled back hair is the pinnacle of “cleans up well.”

In a Shallow Grave pushed Dempsey into a long acting career, but he was just a kid when it all started. And a kid in suspenders!

OK, well I have no idea what’s going on with this outfit. A band collar shirt and a printed vest? Truly an outfit to burn in theory, but young Dempsey naturally makes it look like an expertly curated vintage outfit.

I don’t know why a ringer tee and a leather jacket looks so unexpectedly cool, but it does, and sometimes we don’t have to know why. We just know that it works.

I do think we could’ve done without the tank top layered over the tee, but the head-to-toe white and expert bedhead is worthy of attention and adoption.

Somehow this T-shirt, cardigan, and long jacket feels extremely Chandler Bing but in a good way? Men in layers are good, whether you’re Dempsey, Bing, or neither of the above.

This collar situation is a bit complex, but it helps the whole fit feel more special than a plain navy suit. (Although those have their time and place, of course. But when you're on a red carpet all the time, it’s nice to have simple ways to change it up.)

Wingtip collars are the fanciest of the bunch, and Dempsey managed to make it feel unstuffy with a brown bow tie and slightly tousled hair. Formal made unpretentious.

Well, this is wonderful and please bookmark for the holidays. A turtleneck is a great tool to have in your wearing-with-a-suit rotation, and bonus points if you get one in a fun color that’s still easy to match.

When they say fashion is cyclical, this is what they mean. The loose, silky shirt and oversized pants are quintessentially ‘90s, but they are also reappearing on stylish men today. Take notes.

Wearing a suit vest without a jacket or with a jacket that doesn’t match is generally something we’d keep back in the archives. But if you ditched the vest and opted for the tee under a cardigan, you’d be 2021 approved.

Dempsey’s success in style is all about the details—a fun color here, a mixed print there. A navy dress shirt with a purplish-brown suit and a sneaky scarf very much exude “I know what I’m doing, thanks.”

It is all about the hair here. Please do not get any ideas about wearing a black T-shirt under a silk dress shirt with a navy suit. Definitely get ideas about growing that hair out, though.

Hello, this shirt is amazing, and whoever made it needs to dive back into the archives to make it again. Also long-haired Dempsey is a site to behold.

For the Sweet Home Alabama premiere back in the day, Dempsey went full NYC bachelor on the red carpet, as well as in the film. He does it well.

Dempsey’s style is fun to watch because it has range! When he’s dressing casually, it always feels put together (a button-front) without being showy (buttoned down to show chest hair).