I get into this debate all of the time with my ManFriend. He's an "anti-gear cheapskate" (his words, not mine!) who likes to ride his bike wearing jeans and cotton underwear. Whereas I, am a self-admitted gear *****. I think a lot of gear and sport specific clothing is incredibly marked up. Just consider how much prices drop on an item because it's "last year's model". Did the equipment suddenly "go bad" in that year's time? No way, it just came down to a more fair price. Look how much a new car devalues in the first year, and second year.

Nanci really hit on something regarding long distance riding. For a short rides under 40 miles, it will matter very little whether you have the $50 shorts or the $120 shorts. But on a long ride... yes, there is usually a difference. Anyone doing centuries and longer events is going to find the limitations of their clothing and equipment. Almost every time I have tried to cut corners on quality, just buying something cheap to get things covered, I have ended up going out and buying something that is better quality to replace it. Note - I'm distinguishing between quality and price. There are some really high quality items that are quite economical, and some very shoddy items that are way overpriced. I'm not going to spend $120 on a pair of shorts that doesn't fit me properly, just because they're cool. Nor am I going to spurn a pair of shorts that appears to be well-made and fits me well, just because it "only" costs $50 or it is the wrong brand. But, if I can find that $120 pair of shorts on the clearance rack next season for $70 then I'm very very happy.