I'll be doing this during the school holidays too... swap over my wardrobe from summer to winter so very topical.

I would throw as much as you can bear. I've kept a few sentimental pregnancy outifts... and have them stored in an old suitcase waaaay up in a cupboard... along with my Class of '87 graduation t-shirt and my year 12 formal gown.

With regard to thinking you might need them due to regaining your weight... don't even visualise that! LOL Be positive... assume, like me, that you will continue to slim down (like my mother did as she entered her 40's) and they won't be needed.

How many Op Shops are there in your town? LOL Maybe you could always buy them back if you have a change of heart!