Can't say I've gotten to that point yet. But I have considered what it would be like to live a naturist lifestyle or just taken a vacation at a naturist resort. Getting to be free of clothing, even for just a little while, might be nice.
Giving up on clothes entirely has never appealed to me, but there was that episode of the Simpsons where Homer gets fat enough that he ends up working from home and switches to wearing mumus, and something like that has some appeal. Just loose and draping so never worry about pants falling down or waistbands biting or any of that. It is part of my 'move to a cottage in the bush far from everyone' fantasies.