Maybe it's just me, but it's so much easier to let go of clothes that have become too big for me than those that have gotten too small.
Although evidence (scientific and proven by life experience) says it is far more likely one will regain weight than lose it again, I struggle mightily to let go of clothes I loved when I was many sizes smaller.
It's been happening in fits and starts over the years as I realize my tastes and lifestyle have changed to the point that those items would likely not work for my life again even if I do get into shape and back into that size. But some things are harder to let go of than others. A black and white dotted blazer I always felt good in; a white blazer I stalked Winners for an entire afternoon to find in my size; suits I spent hundreds of dollars on and barely ever, or never, wore.
I did a lot of purchasing in February and am finding that is inspiring me to take another stab at it. Better to have a smaller collection of things I can legitimately wear than a closet full of self-reproach...
This will be easier said than done when it comes to saying goodbye to a few pairs of white jeans I have loved over the years... But I'm going to try!