I've fluctuated in weight quite a bit, up and down by 50lbs+ over the past couple decades. I try to hang on to my older clothes that I no longer fit into, as long as they are still current looking and in good shape - especially if I bought them just before I started gaining weight and never really got to wear them in the first place. This is especially true when I got great bargains on clothes by buying them off season, only to not be able to fit into them when it came time to wear them. No sense in giving them away if I may be able to fit into them again in a few months to a year. That said, I used to try and force myself into clothes that were steadily growing too tight for me, thinking it would motivate me to lose the weight faster, but these days I think it's better to just try and suck it up if you can and start buying some bigger clothes a little at a time if you can. I see it this way, I'm more relaxed and look better in clothes that fit my current size, than being miserable and looking like I'm busting out of clothes that are too small for me. It's easier for me to focus on sticking with a healthier diet if I am more comfortable along the way, and more comfortable with my appearance in clothes that fit me properly throughout the day. It's not worth the added stress and discomfort to be in clothes that don't fit. Not to mention there were two times in particular I almost had some major embarrassments. One time I was getting out of a friends car as they dropped me off at my place, and my pants literally split down the inseam. Thank goodness I was able to quickly get inside before they could have seen it. And the car noise covered up the ripping sounds too, lol. Another time, similarly, the back of my shorts split when I was getting into my car - good thing I was able to go directly home and change.
