I always liked jazz-it's one of the highlights of American culture. I think a big part of it was the fact that the musicians were always so cool. The way they made it seem effortless made it all even better. I got into jazz even more after a few Blue Note compilations that featured their most sampled material. Come for the sick style, stay for the amazing music.
Thelonious. No one rocks a beard better. Makes me want to take up the piano again. 
Art Blakey and the Jazz Messengers. One of the coolest band names ever. One of my favorite drummers. Nothing like a crisp white shirt and a great tie. 
I don't think you can write about jazz and its sartorial influence without at least mentioning Mr. Davis. Iconic photograph for an iconic individual. I think the most important thing you can glean from these fellows is always be yourself and never try too hard. Here's one of my favorites- I could listen to put on train forever :
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