How many times will you patch holes in your cycling shorts before you finally trash them? And do you apply the same rule to your underwear?

I'd rather patch flats than shorts. Hopefully you don't need tire irons and a patch kit to patch up your shorts.

I have several sets of shorts with holes and translucent areas. I still wear them on occasion, but only under my wool tights.

2, the way you have phrased your question!

I know a guy who routinely wears thread bear shorts. I got tired of seeing his crack. I must admit I was guilty of that once. The first day of Cycle Oregon in 2002 a woman who was riding behind me said something like "You must have had those shorts for a long time." It took me maybe 60 seconds to figure out how she knew that, then it hit me. At the end of the day's ride I checked the shorts. Into the nearest trash can they went. I thought it was a classy way to tell me the shorts needed to go.

1) five and counting. mostly when the pad starts coming undone. i've gotten rid of a pair or two when the crack in my ass started showing through. nobody, IMO, deserves THAT visual.

2) no. underwear has 'special' rules that don't apply to cycling shorts. i won't elaborate.

I trash my bibs if the fabric shows any signs of getting thin or worn.

me 2.

Like many cycling questions can be answered, n+1!