At what point did you stop getting rid of clothes that are too big?

Get rid of the clothes that do not fit. I know it is hard to do but just do it. If you have a favorite outfit, get it recut and redone for your new size. It is hard to do at first but the smaller sizes take up less room. I found that out. I went from 3 dressers to 1 dresser and I have a lot more room in my bedroom. Get rid of them and don't look back. I am in a 4/6 right now and the only clothes I am keeping are my size 8. Those will still fit me with a belt. Keeping clothes that are way to big is pointless. 

But if your size 8s are too big, you aren't completely following your own advice... 

There is a difference between saving things that are several sizes too big and things that are only a size bigger (and the OP was talking another keeping 10s and 12s when she wears an 8)

Lora

I wear my size 8 with a belt. 

I never kept clothes that were a size too large. doing that is a subliminal message to myself that I WILL need that size again and gives me permission to gain up to that size because I have them "on hand" and wouldn't have to go out and buy the larger size. 

If my clothes start feeling tight that is a sign to get back on track right away.

This is my thinking.  I don't want to condition myself to getting larger again.

I burned my bridges too. I am about three years and went from a size 26 to a size 0 or 1. I have nothing larger than a size two in my closet. I want to make it expensive and inconvenient to gain weight! Just my two cents worth!

I kept items that are ONE size larger than what I have been wearing(plus I kept three items of clothing from my highest weight as a reminder), but I keep them in a closet in the guest room. I wear some 10s and some 12s (with some tops that are larger because of my bust size), but the only things I kept were looser 12s and one pair of pants that is a slim fit size 14.  I did not keep anything larger than that.

It is a practical matter.  I already spent a large amount of money replacing clothes as I lost weight (I had to have decent clothes to wear to work) and if something happens, I don't want to have to buy them over again.  Although I understand the psychological objection to keeping clothes that are too big (and being able to just wear them instead of losing the few pounds you have regained), the reality is that you might need them... for any number of reasons: the typical (but not unavoidable) rebound weight; regain after a lengthy illness or surgery recuperation or other period of forced inactivity; gaining weight after pregnancy or from taking medication; even because of shifting weight as we age (pants might get too tight in the waist).

For me, keeping the larger clothes in the other room eliminates the psychological aspect.  I would still have to admit a certain level of defeat/failure to pull them out of the other closet -- just as I would have if I had to go out and buy them again -- but I don't have to reinvest the money.  

Lora

I have ALWAYS saved my clothes. I know it seems not to be the popular opinion. I also know that this time I have done something completely different having the surgery and have this new tool that is working wonders for me. I am committed to it and have been doing well. In the past, I have lost and gained so many times and regretted when I did give away both larger and smaller clothing. I invest a lot of money into quality clothing, that I take very good care of and much of it is classic and timeless. Currently I am between a size 12-14 (the 12 is the smallest I have been in my adult life). I have the storage space for the clothes that do not fit (sizes 30-32 to 16/18). It is "out of sight" and does not cost me money. I do not believe it is "bad juju". I am just of the opinion "better safe than sorry". 

I own nothing larger than size 8 and nothing smaller. My days of fat clothes and skinny clothes are over for good. My pants get tight it is time to take a look at what I eat. Military mom so like the burned bridges idea

Clothing sizes are one of my measures of maintenance. 

I wear an 8 in most things. I have a few items in a 10. But I refuse to buy anything larger than a 10 and kept nothing in a larger size. 

If the clothes get snug, I have some work to do!