A fedora hat, sunglasses, a white t-shirt under a black leather jacket, black pants, and black shoes.
actually no,... unless you're trying to look like a ska kid . or tapping into some kind of rat pack vibe. whatever it is, it isn't cool. its "try-hard." look it up. why are you asking other people about cool? are you trying to be cool? better check yourself, spongebob.
Totally depends on the style of pants/shoes/jacket and whether or not it'd look good on you. Some people can naturally pull of certain styles while others just look goofy.
Okay for the fedora & sunglasses, but substitute a soft khaki shirt, go with the black pants & shoes, but do a jacket that SAYS something ~ with a slogan, with a color (or colorS), with a "different" style, with a cool pattern, whatever. Good luck!
I must repeat myself: I am not looking to wear the apparel I mentioned earlier, I am just looking for opinions. However, if you insist, you may continue to make suggestions.