I have observed over my time on this forum that cross dressers tend to not only buy way too many things but also hold on to them, seemingly, forever. I'll put myself firmly in the "buy too much" camp as currently, I have 12 dresses hanging in my closet which is one more than my wife and perhaps almost as many skirts. AND this after recently thinning my wardrobe. Now keep in mind, I am strictly an occasional cross dresser. I could wear something different every time I dress for more than a year with what I own! What I did notice is that all the things I sent to GoodWill (a reseller of used items donated, for our non-US friends) were my cheap buys. All the clothes I kept were quality material, well fitting and fundamentally looked better than the cheap stuff.
I think we cross dressers buy things and keep them like trophies. That's kind of weird because they are just clothes. Somehow I think buying and keeping clothes it's sort of a validation of ourselves as cress dressers. But why buy junk just to have it sit?
My wife always tells me that 1) you need something each season (those of you in SoCal, AZ, FL, and Hawaii don't know what I mean but trust me there are seasons.) and 2) WHERE will you wear this item you are buying? Again, I only go out occasionally so and evening gown is not in the cards but for that matter even a LBD would be a rarely worn item (yet I have two).
So what's the moral of this diatribe? For me it is:
1) Buy less and buy better. A $100 dress is more likely to be worn than 10 $10 dresses from ebay. While there is an occasional great deal on Ebay, $10 buys a pretty cheap dress. On a related note, less buying will make wives happier too.
2) Buy something for each season
3) Thin the wardrobe every 6 months so that the wardrobe is always about the same size.
4) Clothes are not trophies, they are made to be worn and discarded.
5) I need even FEWER shoes! That's a hard one but Zappos allows for returns up to a year!
6) Quality is always better than quantity