The 25 Most Stylish Hip-Hop Videos

Written by Jake Davis (@JakeDavisFilms)

Music videos have always been a great source of style inspiration. The hip-hop genre in particular is one of the most forward and influential of all visual mediums. I put together some of the videos that have had a great influence on me way before I started directing them.

By no means is this list definitive but hopefully you'll discover some gems you didn't know about or revisit a classic you haven't seen in a while. You might even pick up some style tips along the way. Thank you to Complex for the opportunity to share some of the work that has helped shape my own.

Jake Davis is a New York-based filmmaker known for his award-winning music videos for artists like Drake, Trey Songz, and Wiz Khalifa.

Fab Five Freddy, Lee Quinones, and Jean-Michel Basquiat all make cameos in what was the first hip-hop video to play on MTV. Shot in the East Village of Manhattan during a much different time in the city, I think we all had a crush on the uber stylish Debbie Harry.

I shot Malcolm for Supreme a few years back. Not enough can be said about this legend. What an innovator in style and music. Hip-hop would not be what it is today without him. Rest in peace.

Drake is a friend. Anthony is someone who’s work in the genre I highly respect. I read the treatment for this video early on and it was like a twenty page novella (my average treatment is three pages). I didn’t understand a word of it (read: sarcasm) but boy did they make an outstanding video.

It’s all about the suits as Hype pays homage to Scorsese’s “Casino.” Quite possibly the best opening to a hip-hop music video ever.

Spike is a legend for his understanding of high but clever concepts and how to execute them in his own unique vision. He turned what Hype had created for a decade on its head and we loved him for it.

You can’t have a list on style and not mention Mos. I’m going to assume everything he wears in this video is from Union. Ha!

With videos on a tighter budget more than ever this video is a constant source of inspiration for us directors asked to do their thing on a white cyc. The movements, silhouettes, and expressions make it a classic.

How do you make a video about all the things a superstar rapper is supposed to want out of life? Well... you don’t show any of it. I think most people got the subtle style we were trying to portray in this video.

I’ve known Va$htie since our college days when she came over my studio and played her first director’s reel. I’d love to see more music videos from her. This “spec” video is better than most commissioned pieces.

As far as hip-hop goes Harlem sets the most style trends so you could put every Dipset video on this list. But this one is certainly one of my favs.

This is about as cool as videos get. So many incredible style references in this one it’s like a moving Tumblr. Straw Borsalino? Yes, please.

Jada wasn’t fucking around with his wardrobe on this one. Every kid in NYC needed the custom monogram uptowns after this video dropped. Gucci and LV if you were doing it big.

One of Kanye’s most underrated videos to date. So subtle yet so explosive. A femme fatale in a Ford Mustang Bullitt with a shovel. He took it there.

“Flava In Ya Ear” was obviously a starting out point but Sam was able to take the hip-hop video genre and flip it on its head. That type of ideology makes for the most interesting videos.

This one hits on all the cliches of the genre but boy do they do it so well. Captured a moment when streetwear and high-end fashion felt so good together.

Chuck D. in a leather varsity, fitted hat, properly tailored jeans, and Jordans is a classic look that will never go out of style.

Snapbacks, hoodies, and workwear. The more things change the more they stay the same. Classic.

I love when a legendary director tackles the hip-hop video genre in the most beautiful way he knows how. Everything about this video is poetry. Robert Frank meets Richard Avedon.

There are a few directors that can’t be touched. Chris Cunningham is one of those guys. It doesn’t get more hip-hop than this video for Richard D. James. I studied this one day and night during my NYU days.

This dark and edgy portrayal of the 1976 student uprising in Soweto has so much passion and artistic integrity in it the amazing style takes a welcome backseat. Artist and director come together to make something that transcends the genre.

This is another one of my favorite videos of all time. So raw. So real. So NYC. A legendary female director on her gritty. Meth’s eyes are on one.

Ballerinas, custom Phillip Lim suits, and Busby Berkeley-esque dance sequences don’t exactly scream hip-hop but that’s the genius of Kanye. He just makes it all work. A true pioneer... and isn’t that what real hip-hop is all about?

Maybe the best hip-hop music video of all time. The look, feel, and style was so out there for the time... then and now. The “Coming to America” reference and black light scene are incredible.

Too good for words. This video came out of nowhere and brought so much energy back into the art form... polyester suits, aviators, and all.