I wear my t-shirts as long as I can. Might be 10, 15, even 20 years old. When the holes get too big, they shrink too much or they become too unsightly for my wife, they go into the rag bag out in the garage and I'll use them for really dirty jobs and then throw them away. Now that I'm retired, I no longer have a need for dress pants so I've donated a bunch. Shorts are kinda treated like my t-shirts unless I can't fit into them, at that point, if they're presentable, they get donated.