I've come to realize that there will always be stylish, well-fitting clothes offered in the future, often on clearance.
Clothes go out of style, personal tastes change, and it can be extremely difficult to predict how specific pieces will fit once your body changes.
Something I hadn't counted on is that losing weight has affected the way clothes sit on me, length-wise. I bought an awesome leather biker jacket at Goodwill that was a little small for me at the time, and throughout the pounds I've lost it never did fit me properly. I ended up donating it when the circumference was big enough to look comical on me.
Something similar happened when I bought a lovely hoodie that was slightly too small that ended up shrinking in the wash! I never could wear it after that; by the time the length was ok on me it was too big around. And it now sits in my closet, waiting to be taken in so it can fit properly (I'll get to it one of these days, lol).
I love finding ways to motivate myself but basically gambling on "future" clothes isn't one of them anymore.
To be fair I have held on to too-small items in the past when they were given to me as gifts, but I'm done with trying to guess what my body will look like next month, next year, etc.