I do.. for me the emotional attachment is having a bit of a fear of throwing something out that I may regret.
Especially as it happened last night, realised I had tossed DH's summer pyjamas because he never wore them, so of course as soon as I toss them, he starts looking for them!
But I pointed out to him that he hasn't worn them for a long time, but still I felt a BIT bad for giving away something we will now need to replace. Overall I didn't feel too bad about it because his shelves are so nice and clean now.
When it comes down to it, I think well OK it's just a pair of PJs that are not expensive, so i try to work out why it makes me feel bad.
I think it goes back to my childhood and the guilt about waste, as we never had much money, so having tossed the wrong thing is like a failure feeling....which kind of gets me in the pit of my stomach....
BUT I have to remind myself that regretting a few things is really much preferable to having clutter! I have got rid of hundreds of clothes and really only had second thoughts about a couple of things, so I think that overall the benefits have FAR_OUTWEIGHED the losses.
So if you are drowning in clutter...try to remember a few things:
If you live in a western country, clothes are usually inexpensive to replace.
Your clothes need to be easily accessible otherwise you won't wear them, so having them jammed into a closet will mean you wear even less of them
most people wear only 20% of their clothes 80% of the time
you don't need 20 white T-shirts (just as an example)...so avoid buying duplicates of an item you like to wear, and if you have duplicates get rid of them.
Get rid of any tatty or uncomfortable underwear...only keep the ones you always reach for.
If you are keeping clothing due to the memories it brings back, you are keeping yourself stuck in the past, and not allowing yourself to be open to good things happening to you in the future. If it is really that important to you, take a photo of the dress/t-shirt etc, or cut a small piece of it and keep it somewhere, such as stick it in a scrapbook with some notes written about it.
One in, one out...if you plan to buy a new clothing item, make a decision to throw another one out.