At what point do you pull a shirt from your closet, about to put it on, take a double-take of it, and think "You know, this isn't really decent anymore to wear in public" and then think either "I should throw it away" or "I should donate it"?

For me, donation is never an issue. Because the only time I stop wearing clothes in public is when they stop serving their primary function: to keep that part of me warm and protected. So I throw it away at that point, because it's no good to anyone.

Yes, this leads to me getting stares when I'm wearing a shirt riddled with moth holes or underwear with a hole under the elastic, or shorts that have a stain on them from 3 years ago. I even have a shirt where the only thing wrong with it is that the hem of the arm cuffs have separated and are only half-hanging on. So every time I wear the shirt, I have to thread my arms through the hanging loops so that the hem is around my arm properly and I get made fun of for that shirt all the time. But I'm not gonna cut off the cuff hem (since that causes the fabric to roll and that would be even more unsightly and uncomfortable). So I just deal with the stares. I don't mind.

But I wait for the extreme cases. I'm certain there are some people who'll donate clothes as soon as a single pin-sized stain appears that detergent can't remove.

How long do you keep your clothes?

I perform light maintenance on my armor every few days, and get it professionally maintained and mended every few months. That way, I have not had to replace it; it's still the same armor I crafted by the one and only Six Winged Angel, the same armor that survived the great battle of Enzo Matrix. 

Granted, I don't get out much, but I'll typically wear a shirt until it looks like I've been mauled by a wild animal. In fact, I still have a shirt I wear sometimes that I got back in... 2011? 2012? I can't remember. It's darn near in pieces now. I typically wear it around the house in the summer because it breaths real well.

I get wanting to look nice and everything, but we don't get to buy clothes much. Maybe once a year, and not may at that. If clothes look worn, it's because they are. If there are a few small stains, big deal. People get dirty. Clothes get dirty. These are things that happen. One's gotta draw a line between being clean and being vain.

depends on the shirt for me. my button up shirts i stop wearing when a sizable hole appears in it. last button up i threw away had a hole at each elbow, wore it for a longtime but eventually the holes got so big i mightve well have not had sleeves. for t-shirts though i wear them until it just isnt feasible. my current tshirt has like 6 holes in it, most are small but theres 2 pretty big ones, i dont worry about them cause theyre in the inner arm area though. the wording is extremely faded and torn as well so its not looking great, only time i wear it outside the house now is if im going on a quick run the the corner store near my house.

I find this topic interesting, to be honest. How some people view clothing like Zeldizaster does, as simply a functional necessity. On the other hand, some people view clothing as also a form of art, and therefor take interest in the way it looks.

What's interesting, is how many of the "I don't care about clothes" people, seem to think that that concept is logical and they are not conforming to societies obsession with appearance. But really... it's just like any form of art or expression, isn't it? It's like putting a cool picture on your wall, a decal on your PC, a tattoo on your skin, or one could even make a stretch and say it's like playing music in your car. It's simply a piece of aesthetic that pleases the person using it.

But like all art, it's not for everyone. Some people might have no interest in paintings or tattoos, same as some people have no interest in the art of clothing.

I usually don't wear shirts since I generally just prefer wearing dresses all most of the time but when I do wear a shirt I would probably wear it for 3 days at the very most.