You're right, Encore wasn't a great example... but earlier that year was D12 World. Listen to 40 Oz. and see how they were dressing around that time. Im Going to Get my Gun, Quit Talkin...
Eminem's verse from Git Up:
10, 9, 8, 7, 6, 5 ,4, 3, 2, 1
Ready or not here we come, here comes trouble in the club
11, 12, 13, pistols big as M 16's
How the fuck we sneak in with this many heaters in our jeans
Nina, 2 nina's, a piece and they don't even see us
Some shit pops off we squeeze each one they gon' think its machine guns
Vanos vo vano, bananas in our flannels
Hands around our colt handles, hold them like roman candles
Vannas vo vannas, banana fanna fo fannas
Who come back all bananas, banana clips loaded
Managers, bouncers and the club owners, the motherfuckers don't want us
To come up and rush in the club and run up in it with a bunch of
Motherfuckers from Runyan, steady popping them onions,
Ready set to go nut up, prepare to tear the whole club up
Fixing to get into some shit just itching to choke someone up
You know we finna loc'n when we mixing coke with coconut rum up

Just for starters

Okay, and then Encore came along. We have One Shot Two Shot, Spend Some Time, We As Americans. But you can't deny Eminem was flirting with gangster imagery around 2004 and beyond