The Kempt 100 is our definitive list of the 100 best-dressed men of the past 100 years.

Presenting, the second installment of the Kempt 100, starring some of the musicians and politicians—yes, politicians—with the sharpest attire. (And let us remind you: if you don’t see your favorites today, you might just see them when we get to the Legends and Gods portion of the list later this week.)


0113hundredANDRE3000Andre 3000
The takeaway: Being arguably the only late-’90s hip-hop guy to don a shirt and tie gets you onto a lot of best-dressed lists. Some of it has not aged well, but Andre’s less costume-y, more down-to-earth looks are still plenty covetable.

0113hundredBLAKELYArt Blakey
The takeaway: Mad passion. Slim ties. Cool under pressure, even when wearing a suit. It all works.

Cale And ByrneDavid Byrne
The takeaway: Rock style can have a preppy touch. (Somewhere, Vampire Weekend was taking notes.)

0113hundredCOCKERJarvis Cocker
The takeaway: A well-tailored suit, worn with a bit of scruff, is as rock-and-roll as any leather jacket.

0113hundredCROSBYBing Crosby
The takeaway: Der Bingle: great singer, greater hair?

0113hundredDAVISJRSammy Davis Jr.
The takeaway: Exhibit A on why the best part of wearing a bow tie is unwearing a bow tie.

0113hundredDYLANBob Dylan
The takeaway: Don’t try this look unless you wrote “Isis.”

0113hundredELLINGTONDuke Ellington
The takeaway: When worn right (and when worn often enough), a suit can look and feel as good as pajamas. Well, almost, anyway.

0113hundredHELMLevon Helm
The takeaway: Every man should have a picture of himself with a full beard. Ideally from work, and paired with a wild shirt.

0113hundredDEANMARTINDean Martin
The takeaway: Any man can throw on a well-tailored suit and look good. Pulling off a turtleneck and a loud jacket takes style.

0113hundredMCCARTNEYPaul McCartney
The takeaway: Sure, he put on a master class in style in the ’60s, but we’ve been digging Sir Paul’s ’70s swagger.

0113hundredMCLARENMalcolm McLaren
The takeaway: Punk rock isn’t wild hair and a big leather jacket; it’s an attitude. And yes, it can be expressed with loud trousers.

0113hundredRAMONEJoey Ramone
The takeaway: Then again, sometimes punk is wild hair and a big leather jacket.

Lou Reed and Nico in the StudioLou Reed
The takeaway: Why do we get the feeling wraparound shades are due for a comeback.

0113hundredRICHARDSKeith Richards
The takeaway: If you’re comfortable in your own skin, it doesn’t matter how damaged or wrinkled your skin is.

0113hundredROBERTSONRobbie Robertson
The takeaway: A great scarf is something you can wear forever. (And yes, that is Martin Scorsese on the left; we assume he was doing research for The Wolf of Wall Street.)

0113hundredSIMONONPaul Simonon
The takeaway: You don’t have to be a frontman to dress like one.

0113hundredTIMBERLAKEJustin Timberlake
The takeaway: Never give up. One more time: never, ever give up.


0113hundredBUSHGeorge H.W. Bush
The takeaway: It’s been a while, but once upon a time, our leaders dressed like, well, leaders. And that was as true on the right…

0113hundredLINDSAYJohn Lindsay
The takeaway: … as it was on the left. (Hat tip to ACL for the pic and inspiration.)

NOTE: Click here for the previous installment.


  • Kempt Staff