Join Date: Mar 2005
Location: Philadelphia, PA
Bikes: Jamis Aurora
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OK Here's my take...
The fit has to be snug in the middle of the crotch (directly between your legs, behind your balls). That prevents them from coming down and getting in between your legs so they get shoved around as you pedal (not comfortable). In order to be snug there, it usually has to be snug around your butt (pull 'em up far enough in the back). In doesn't have to be super-snug in the front, but if it isn't snug enough you'll get some chafing as Mr. Johnson wanders around.
Too large shorts won't be tight enough. Too SMALL shorts, ironically, also won't be snug in the middle because they'll be stretched too much and you'll get an open area there.
I haven't tried a lot of shorts/tights, but the ones I've worn are usually most comfortable if I make an "adjustment" shortly before getting on the bike, because your position while walking causes your guys to be in a bad position when pedalling. But once in position they'll stay there.
Treasurer, HHCMF Club
Now living in the land of the cheesesteak.
But working at a job where I can't surf BikeForums all day any more...