$500 is pushing it with that wardrobe.
with clothes like that, he's better off with a $10 BLING BLING watch from walmart.
OP's gotta lose the sneakers and timberlands and head to Zappos drop a couple hundo on a couple pair of Rockports.
... and lose the fucking "fitted caps".
what kind of impression are you making wearing that shit? u still wearing jerseys??? holy fuck. what has MTV/BET done to ppl.
get some proper pants also... and shirts... with buttons.... that FIT.
even if you're in a t-shirt and jeans (that fucking FIT, btw), a proper watch is all you need. (besides shoes).... i'm a Panerai man, myself. if I want something bolder/bigger, I go with a Uboat Flightdeck (50mm) although i'd never wear them outside the gym or running errends on the weekends.... I believe the panerai (Luminor Marina) is 46mm... maybe 44mm, plenty big and bold, without being stupid.
drop the cash on a proper swiss automatic, even if you gotta make $50 payments. Rolex and Movado are cliché. go with panerai. it's not like buying a car for $3k and turn around and sell it for $1200... a $3k swiss watch resell for $3k next year or 5yrs from now.