I think it's really personal, as others have said. It would be too limiting for me even though I enjoy repeats.
I really like Laura's questions (figure out what it is that appeals) and Barbara Diane's suggestions.
Trying it out while keeping many of your current items in a hold zone sounds feasible. Just don't toss it all until you know for sure.
Some people really love this approach and replace most of their wardrobe yearly. If one has the budget and likes repeating outfits I suppose that's a way to go.
On the subject of wear, I must be harder on some of my clothes than others on the forum. Because even though I have a medium-to-large wardrobe, I do wear things out. Not everything, of course. But I pass on (edit out) more due to wear than due to boredom or style shifts.
Perhaps because I have quite a variety of roles, but some dominate, meaning certain items become real workhorses and get worn a lot more often than others? I honestly don't know. I mend. I launder carefully, don't launder items that don't need washing, and barely use a dryer. I polish and maintain.
Even so, I typically wear my favourite jeans out in one year (worst case scenario) to three years. Shoes and boots last about the same length of time, except for tall boots which I wear less frequently. Sandals often last only one season. Granted, I walk a lot more than most people.
Knits last anywhere from 1 season (at worst -- so frustrating!) to 5 or so. They definitely show their age sooner than woven items.
Coats last because I have a decent collection. Blazers last. Some dresses last (and some don't) -- but I wear them less often.
