My attachment is to shoes more than clothes.
I have a pair of very high wedge baby blue sandals that I bought strictly as a joke for a trip to Niagara Falls with the car club I belonged to. We had some chat convo about "fuck me" shoes or something.....I brought them to the event, put them on and a (newly met) chat friend took a picture of them. I wore them the rest of the day even though I could NOT walk in them very well, but my feet looked goooooood....a year later at another event down south, the same friend whipped out that photo of my fuck me sandals and proceeded to try to auction it off. They're still in the closet 8 years later. I have probably about 20 or so pairs of shoes, many out of style, but I can't get myself to toss them. I did toss out about 10 pairs of boots several years ago and it took a while for the garbage bag to make its way downstairs.
I do have a problem letting go of clothes that don't fit. If I gain weight, I want to keep my "skinny" clothes. When I lose weight, I don't want to toss my fat clothes without agonizing. I did keep some (I lost the weight in 1999) and now they fit again.
I once had 64 sweaters and got into a mode of "WTF am I doing with 64 sweaters?" and gave away all but maybe 15 to a women's shelter.