Shorts just like saddles are very personal. What fits one person well will not fit the other. In general though look at the chamois, does it look like it had some thought process put into it or does it look like a chunk of carpet padding put in it (an exaggeration). Also the stitching. Again does it look like a quality pair of shorts. The number of panels that make up the shorts. The increased number of panels means increased range of motion. Usually the more you spend does actually correlate with the quality of the short. You do not need a 200 - 300 dollar pair of Assos to be comfy. Try them on. Also pick the LBS staffs brain on recommendations. Tell them what type and duration you think your rides will be. How ofter you will be riding. Also, personally I like bibs. Have them show you a pain of those. To me and again this is subjective, much more comfortable than shorts and I don't get plumbers butt.