I seem to change teams or the team changes kits before anything wears out. The bibs then get assigned to trainer duty - I have a few totes next to the trainer that I just toss outdated-kit stuff in. Okay, I also have a pile of clean clothing next to the trainer too.

Out of that stuff, the oldest bibs I'm wearing are ones from about 2001 or 2002. I wore them quite consistently on the trainer within a year or so, and I ride the trainer year round (it's just easier for me to schedule). I'd wear them outside if I had to.

I should point out that on the road I rotate through 4-5 pairs of shorts, 2-3 knickers, and 2 tights (all with chamois so they're base layers; I have "over" knickers and tights as well). Therefore I may not wear a pair as much as someone with 2 pairs of shorts (for example).

On the trainer I rotate through about 15-20 pairs of shorts, so, again, I don't wear the shorts as much as someone with fewer pairs. There are shorts, nice ones, that I've never worn outside for political or whatever reasons. Ditto jerseys.

I have stuff from the early 90s that I have just to have. I wouldn't wear them, even on the trainer. The kits are more for collecting.