Riding in style requires some sense of style, that is a purposeful arrangement of what you wear in order to achieve a certain effect. A mix of fashion, comfort, and utility, your style must allow you to ride comfortably and safely while conveying your personality.
Helmet (spray-painted skateboarding), dope looking sunglasses.
Muscle shirt, to show your muscles and tattoos, and also to stay cool.
Big shorts, for comfort, and also to clash with the conventional yet indecent bicycle shorts.
Pocket knife, for protection against feral pitbulls... a bike chain, and pepper spray can add several layers of intimidation, in case you have a run in on the road. Let's hope we never have to use those.
Cool leather gloves to absorb handlebar vibrations and save your hands when you fall... Wrist watch to know what time it is, and how long you ride for.
Shoes with a semi-hard sole and some good grip at the bottom. I personally found that Sketchers are awesome for riding. The worst are Converse (you feel the pedal cut in your foot bottom).
A phone, for emergencies, preferably a cheap one, so that it doesn't attract envy.
Winter gear coming up!