For me, I didn't need bike shorts until I was riding over 20 miles at a time. I started with the Cannondale Domestiques (not sure they still make them - got them on closeout through REI Outlet). These were good to about 40 miles, but not so good for longer rides. I recently got a pair of Shebeest Ultra D's. These work well for me on longer rides. The only thing I don't like is the drawstring - it cuts in if I leave it tucked into the shorts, but flaps in the breeze if I leave it out. Luckily my jerseys are long enough, but there is a mesh portion to the shorts at the small of the back and someone here got sunburned through the mesh. The Ultra D's are quite pricey (almost $100 at 25% off plus tax), so I hope they last a long time! I handwash my shorts in Woolite and line dry.
Oh, PI stands for Pearl Izumi - the designer of the shorts.



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You can save some money by buying mid-range shorts for now. Look at TE's SALE shorts. You are not going to need heavy duty chamois for 20 mile rides, but *some* chamois would be nice.
