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Off the top of my head, in no particular order:

Red Wing hunting boots, pre-1970.
Cowboy boots by Justin, Tony Lama.
Rayban wayfarer sunglasses
Persol Sunglasses (not just the ones McQueen wore in Thomas Crowne)
Desert boots.
Chelsea boots.
the black turtleneck sweater
web belts
army fatigue pants (I'm partial to OG-107's)
the safari jacket (particularly the 1952 British military one)
Longwings (the Florsheim Imperial would be iconic)
the black leather motorcycle jacket
the cowboy hat
the fedora (think Bogie)
the porkpie hat (think Sinatra)
and don't get me started on iconic wristwatches...
 
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