Gear Selection

There's nothing wrong with spandex as long as nobody has to look at it. So get a good pair of spandex bike shorts and simply wear them under your normal shorts. Nobody will know the difference and you won't be in pain on long rides.

As far as shoes, you need to be able to walk, so although road shoes are great on the bike, you can't even walk in them off the bike. The Adidas El Moro is a great choice. You can wear these shoes on and off the bike, run in them, and still get the benefit of cleats.

Carrying your stuff is easy with a Timbuk2 messenger bag. These bags last for ever, are waterproof, and most of all, they have the ability to add accessories.