When it's warmer, I favor searsucker shirts. They're SUPPOSED to look wrinkled, they're cool, and mine all have buttoned pockets. My favorites are made by Patagonia, and they've all been purchased at a nearby Patagonia outlet's annual sale, when the prices descend to reasonable heights. Shorts: More than 40 miles, Andiamos (Thin, padded, cycling shorts designed to be worn under other shorts, and whatever loose, comfortable shorts I have at hand. I find mountain bike shorts to be a bit hot, but the andiamos breathe well and work fine with whatever outer shorts suit you. As it gets colder, I switch to a merino long-sleeve jersey, a bit on the large size, and if it's really cold, real bike shorts with a looser pair of tights (I think they're called "Cafe Pants."