I think I wear clothes for way too long I have a very hard time giving them up. I have clothing in my closet that's way too big for me (and was too big for me at my highest weight) but giving them up is still a difficult thing to do! Not to mention, I honestly only own a handful of shirts and, right now, 3 pairs of pants. I own ZERO long-sleeved shirts (and I live in New England for crying out loud!)
Truth is, not only do I have a hard time throwing away or donating clothes, but I also have a difficult time convincing myself to buy clothes.
All but one pair of my pants I've worn since High School (graduated in '07). About half of my shirts are from High School too. (I'd probably still own my middle school clothes had I not gotten too big for them.) Most of my shirts have lost that... newness to them. They're kind of stretched out, the colors are fading, they don't look terrible but they're not beautiful either.
How long should you reasonably hold onto a piece of clothing for? A year? Two years? Three? When do you know that it's time is up, and you have to move on?
I'm of the opinion that clothes should give you pleasure, and if they don't, you shouldn't bother keeping them.
When you put them on, you should feel good about them & they should set you off & help you in some way.
If you don't feel good in them, if you feel they're uncomfortable or you never liked them, really, but kept them anyway, or they need mending (and you don't want to mend them or take them somewhere to be fixed) or they don't really fit, or if they are stained & faded, you should get rid of them.
Now.
Because they're far from irreplaceable.
The world is overrun with clothes. They fill up the stores in every mall. They're available online. They're all over eBay. They're all over the thrift & second-hand shops.
You don't have to care for them passionately, or to be really into fashion, but you do yourself a disservice if they aren't presentable-looking, if they're really old & faded.
How do you feel about shopping for clothes? Do you hang onto what you've got because you hate trying new things on? Or is it spending $$ that you hate?
As for when you should get rid of them, it's hard to say. Depends on the individual garment, how well it was made, how it's been treated over the years, and how well the style holds up. Along with new clothes, I've also got vintage clothes from the 1910s and 1940s-1990s, but the thing is, they are all presentable & wearable. I've got a Lands End candy-colored striped cashmere from five years ago that I know I'm getting rid of very soon, because it hasn't worn very well, but my very thick 1950s Scottish gray cashmere cardigan still looks great.
Maybe watch an episode or two of "What Not to Wear" to help you start thinking about whether you want to update your look.
You're definitely worth it, you know. Having nice clothes, I mean.
I had a favorite pair of laced boots that I got in high school and wore until they drowned in 2005. I'm 41. Those were some old boots.
It's time to move on when the garment no longer fits you or when it no longer looks anything like how it looked when you first brought it home. If it gets stained, torn, pulled out of shape, or unraveled, toss it (well, unless the thing happened to get torn, pulled, or stained in an aesthetically pleasing way--no need to dump your favorite shredded jeans if you love them, just don't wear 'em to a job interview). Learn to develop an eye for what looks shabby-chic and what just looks shabby.
If you do what I've done all too often and buy stuff that you hate once you get it home, return it if possible. If not, donate it. In fact, donate all the items that are in wearable condition; giving away items that'll make someone else happy is one of the very few ways to feel drastically lighter without ever losing a pound.
I'm the same way. I have clothes from my freshman year of high school and I graduated in 2000. I will throw out jeans that rip, tear or are worn through to the point of no repair. T-shirts will be worn (at least in the house) until they're falling off of me. My husband has tossed some of my really heinous clothes behind my back. LOL. I had a Pink Floyd t-shirt that was TOTALLY ripped up. The collar was coming off, both sleeves had holes in the arm pits big enough to fit my arms through, there were random holes and bleach stains all over it, and I was still wearing it around the house. Sometimes I'd toss a hoodie over it and wear it out. It's not that I couldn't afford to go buy a new one, I just... couldn't. I have since tossed it. I found an identical shirt and finally retired the old one.
I tend to wear clothes out. I hate hate hate clothes shopping, always have, so if I can avoid having to go, I will. My new excuse not to go shopping is "I'm going to wait until I'm below 140 to go shopping." Hopefully that doesn't sabotage my weight loss. LOL!!