A Masi Speciale! That's a nice bike for $1,675. Very solid commuter, excellent steel frame painted in a cool root beer brown, decent Shimano running gear, pretty good Ritchey wheels. The frame is the winner here—the parts and wheels probably won't last more than three years, but it's well worth upgrading this bike with stuff you find on sale, on Craigslist, and so on.
Anyway, it sounds as if you need footwear. That's a bit tricky, as I assume you're riding with clipless pedals, so you're looking for a bike-specific shoe that has a little bit of street cred. But there are some shoes out there. Try the Keen Austin Pedal Shoes ($120). They're patterned after urban trekking shoes, but have a three-quarters-length plastic insert and SPD-compatible cleat plate. So you can clip into the bike, un-clip, and walk around work and campus without looking like a bike dork.
For something a little more technical but still street-friendly, Shimano's SH-MT32 shoes ($60) might be an option. They're black lace-up shoes that look like a cross-trainer but have SPD compatibility and are designed for both walking and riding.
Of course, you don't HAVE to ride clipless pedals. You always can ride cage pedals and then choose just about any shoe you want. The Keen Coronado Cruiser ($80) is a good choice. It's a sneaker made of a funky mix of suede and canvas with a patch of soft rubber under the ball of your foot to better grip the pedals, so it's cycle-friendly without screaming "I BIKE!" You even could ride with something like Merrell's World Era shoes ($110), which are a classic urban shoe, with full-grain leather uppers, comfortable sole, and a traditional lace-up design. You could bike in those, easy.
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