I suffer from similar tendencies. One thing that helped was having my wife decide what I should wear, another story. Now I've got new stuff numbered, and will pick one at random and wear it. Always more fun than just knowing it it there i the closet.
Since CD has an element of secrecy, it is way too easy to fall into the fear of loss mindset- and grab anything and everything when the opportunity arrives.
One of the turning points was when I finally bought a cheer outfit. Not a costume. Costumes are cheap & flimsy. After too many years, I splurged one halloween. "Only" $200 or so, including thin streamer poms- (like they had in the 70's & 80's) a skirt & shell with nice trim and piping. I put the name of my wife's alma mater on it, along with her school's colors... When my wife first saw the uniform- she was impressed- heavy quality material, well sewn and fitted. SO worth it.
Pretty much now I'll restrict dresses or outfits to costing a fair amount- medium upscale i guess. Never been unhappy with the purchase- in fact, even having shopper's remorse for not saving the money and getting something even nicer!
Yes, fad -wear is fun, but quality classics are worth investing in.
