I'd wear all the classics: Mascot eyeglasses, Levi's 501s, Clarks Desert Boots, Paul Smith socks, brown leather belt, gingham shirt.
I'd read these blogs:
The Sartorialist (in moderation)
The Selvedge Yard
A Continuous Lean.
Edited to add:
The Impossible Cool.
(1,001) Rules for My Unborn Son. (any guy's social bible.)
Ivy Style
The Selby
I'd subscribe to:
Esquire
dwell
The New Yorker
McSweeney's
On my bookshelf:
Bukowski
Hemingway
Kerouac
Faulkner
Vonnegut
Hornby
Klosterman
Sedaris
Eggers
Martel
Chabon
McEwan
On the stereo:
Thelonius Monk
Neil Young
Jimi Hendrix
Charles Mingus
Otis Redding
Johnny Cash
Al Green
Joao Gilberto
Style icons:
James Dean
Steve McQueen
early Marlon Brando
Basically, I'd be a little bit cliched, but a lot awesome.
