I’m going through my closets for the semi annual season switch. As I’m going through my fall and winter wardrobe, I have lots of pants, cordoroys and jeans that I have hung on to over the last several years. When do you finally let things go? A certain amount of time that you haven’t worn, color, style. I’m guilty of thinking I might need that dress I bought 5 years ago and worn twice. Those are perfectly goid cordoroys, even if they aren’t in style. Argh…
Great question - I’m looking forward to seeing how others handle this. It is always a dilemma for me also.
I have not changed size since I was in my 20s (knock wood…). I do still wear sweaters bought decades ago and I have “favorites” hanging in my closet that I still love, but don’t want to wear since they aren’t stylish. At this point, such items are in a guest bedroom closet. I keep thinking maybe some day I can wear them as “retro”! Unless an item has hit the “favorites closet”, I do get rid of no longer stylish items that I would be embarrassed to be seen in, even when they are still in good shape.
I remember as a young professional seeing older women who were clearly wearing decades old styles. Now that I’ve hit the “older women” demographic, I have greater understanding and empathy with those unfashionable oldsters!
I used to hang on to clothes for years. I’ve lost 60 lbs since the end of January so I’m dumping clothes left and right.
I’ve held on to one piece of clothing long term. It’s a wool suit that I bought back in college for interviews. I should drag that out and see if it fits, because I might actually be too small for it now. If so, it’ll get donated too.
I just picked up a pair of cords at Old Navy. They must be coming back into style!
This is on my “to do” list. I think the rule of thumb is toss it (or donate) if you haven’t worn it in a year. Or if it’s stained or doesn’t fit. It’s tough especially if it was expensive or a gift from someone you see often. I have work outfits I’m going to toss simply because everyone at work has seen me in them too many times 
I just wore a pair of slacks the other day that are very loose and baggy–time to donate as unfashionably “hanging.” I will have to to thru my other slacks and probably donate others as well.
I have a lot more trouble with discarding tops, some of which I’ve had for decades. They are classics, so still ok to wear. I have donated a few but have to work harder at it because our small closet is still full.
Except when pregnant I’ve been about the same height and weight since I was a teen, so it’s tough to discard “perfectly good things.”
I clear out when I make the semi-annual closet switch and when I buy something new I look to see what is old in that category and bin it. I went on a mini shopping spree a few weeks ago, came home and discarded several old pair of leggings and jeans. I also threw in the bag some sweaters I’m just not going to ever wear again.
“When do you get rid of clothing?”
I get rid of my bra and shoes as soon as I come in the door. Loose my pants and shirt for pj’s once dinner is over and the kitchen cleaned up. Loose the pj’s as I pull back the covers on my bed. Sleep with no clothes. Best time of the day.
my W decides for me
When I’m cleaning closet I make three “go” piles:
- Great condition, brand and style - EBAY pile.
- Not stained and good condition, but nothing special - GOODWILL-type drop off at church.
- Stained and/or damaged - TRASH or rag pile!
I get rid of clothing when it falls apart. I don’t care how old it is, who made it, what it costs, who says it’s in or out of style. If it fits and has not become transparent, it’s good to go. I don’t collect or hoard clothes or shoes or anything else. One pair of sandals, one purse, a couple of skirts, three or four tee shirts, etc. is fine for me.
I was keeping a couple of really nice suits that I hoped my son would be able to wear someday. The last time he came home, he tried them on–and he’ll never be big enough to wear them, so out they went. My biggest problem is with clothes that are a little bit too small, so that it’s not outlandish to think that I’ll be able to wear them if I lose a modest amount of weight.
I broke my ankle about 5 weeks ago and have been wearing long dresses that were in the back of the closet for years. I was desperately looking for an old denim dress that I needed to wear to a themed party, and feared I’d donated it. I was thrilled to find it in my s’s closet (where other old clothes go to die). This has caused me to justify/rationalize keeping old clothes (even though I did rip out the big shoulder pads!)
I hear the shoulder pads might be making a comeback (shudder!). 
We downsized last year and I had to get rid of a lot of stuff (about half) over a few months. Needless to say I have missed very very little of that. But my method was different this time than previously. This time I went thru the clothes and pulled out the stuff I love and couldn’t live without. Stuff I wear every week. Stuff that makes me look my best.
THEN the balance of the stuff I told myself that I could keep half. And that kept half was on probation. After a couple more months if I hadn’t worn it…OUT. Because, of course, most of us go back to the same thing day after day, week after week.
I am trying, but still fail at getting rid of stuff that is in good shape. I finally got rid of the shirts from a number of years ago when shirts were quite short and had to wear something under it, or constantly pull it down. The slightly too small or too big stuff is also a challenge, since I have not been the same size since I was in my 20s! On my to do list, but definitely not something I do well.
To answer the question in your title: trashed when there is a hole in the clothing. (Most of the time)
Otherwise it goes to Goodwill. (occasionally)
Every few years I go through my closet and get rid of stuff in bad shape or that i am certain i will never wear again. I probably don’t do it often enough. I do keep a few things I will never wear that have good memories attached to them. I just like to look at them.
I go through my closets and drawers thoroughly at least 2x a year. I used to be more sentimental about keeping things but I have become much more ruthless year by year. I have a certain style of clothes that I wear to the office and try to stick to that. I have a pile of stuff for the trash, for the high quality thrift shop who are picky about what they will accept and you get tax donation receipt for and stuff for clothing bin. What is harder for me to get rid of are things like dressy dresses… sometimes you keep and assume you will use, others you keep because hard to part with and I tend to want to get something new when it is special occasion anyway.
When you have a hard time parting with things that are still in “good shape” - think how wonderful it feels to be that Goodwill shopper or person gifted with used clothes for whatever reason to find/receive an item that is in GREAT condition as opposed to old wore out stuff.
I got a huge reality check when I brought a large stack of name brand clothing in near perfect condition to one of those resale shops. 80% of it was handed back to me. Reason given: No longer in style. Ouch!!