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Skinny took two pairs as I think he found one would stretch too much (or more likely he'd get too skinny!) so it didn't fit well. I've done TCR and TABR with one pair and managed ok but since the weight/space savings aren't great (they squish innit) will probably take two in future because mine definitely stretched during the race. Touring, no brainer, at least two.
I've done both. Taking two is nice because you can switch if one is giving issues (I use pairs that have different chamois designs) and it's possible to double up if your undercarriage gets real bad. You're also more likely to get a second pair clean and dry compared to if you're limited to one.