I wear a jersey and riding shorts (I've just begun working in my Brooks B-17) but I then wear a light Nike dri-fit t-shirt and a pair of cargo shorts over the riding shorts. I also wear a helmet, Shimano SPD shoes with my clipless pedals since my area is also very hilly. I still have a bit of a diabetic gut so I tend to be very conscious of it but I'm slowly whittling away at it Now that fall is upon us here in Stockholm and winter is close on its heels, I'll have to make a decision about whether or not to do some winter cycling or to put the bike away until the snow clears.