CLOSET CLEANING: DRESS KEEP OR DELETE

Since this summer is a summer about new beginnings and fresh starts, I decided to give my room a li'l makeover, starting with my awful closet. The curse of having a walk-in closet is that you can literally just stuff everything in there and not think about it until like 2 months later when you're actually looking for something and it's buried under 8 tons of junk.
So while I'm cleaning out my closet, I've decided to get rid of a bunch of stuff and give it to GoodWill. I happen to have accumulated several dresses, both thrifted and new, over the past 6 years and it's time for me to decide: should I KEEP or DELETE? Here are some bad photos of some of the dresses that I internally fought over:

this weird connected lacey skirt + top that I got last year at Karma. (keep)

A long, bright red thrifted dress from the 80s that I actually love a lot but actually look horrible in (delete)

This cool floral dress from  ragstock that's made out of some weird swimsuit material but is actually my favorite thing ever and I don't care what you say (keep)

Another thrifted dress from who knows when, that I love, even though it is not flattering whatsoever. I WILL FIND SOMETHING TO DO WITH IT. (keep)

An odd stripey pink thing from h&m that I like but not enough to handwash it every time (delete)

A way cool velveteen dress from urban outfitters that's perfect in every way and oh my god it's the best thing ever but I can really only wear it in december with thick leggings (keep)