Chrome bags makes some nice street shoes with a fiberglass insert to make the sole rigid enough for biking (so it doesn't flex over the pedals making your feet numb.) With a gnarly tread that grips the pedals and a small reflective strip on the heel. They look like Chucks but made functional for biking and a big plus to me, they don't look dopey like some cycling shoes.
They run about $70 - $100 dollars depending on the model but they are pure style. Get some of these and run toe clips.
"Things look different from the seat of a bike carrying a sleeping bag with a cold beer tucked inside." ~Jim Malusa
2009 Trek 520-Brooks B-17 Special in Antique Brown
2010 Surly Long Haul Trucker-Brooks B-17 Standard in Black
1983 Fuji Espree Single Speed-Brooks B17 British Racing Green