@Bimmering i am exactly the same!! I'm so bad at buying the plainer, practical pieces because they are not exciting yet they are the key to making the more beautiful pieces wearable!
I don't know why i'm so resistant to it other than that i'm irrestibly drawn to beautiful & interesting clothes similar to you. And likewise i don't always have places to wear them.
I also downloaded the Whering App & uploaded about 40 things over the holidays but then got a bit bored & stopped.
I didn't realise other people could see your stuff & i am not sure i like that idea. I might come back to it...
In the meantime, having bought a couple of special things recently, i am now working on finding ways to make them wearable in a range of ways - such as a beautiful patterned skirt & i have worked out 3 different tops that brings it from super dressy to more casual.
I find footwear is often the hardest part to get right & i'm v fussy about shoes & boots. I invested in some v expensive shoes & boots over the past 2 years & that gives me a far greater range of options prticularly for wearing skirts & dresses more frequently
I think i will focus on the dull but necessary items for the next while - jeans, plain tops to wear beneath things, plain knitwear, new scarf etc
And i saw someone else mention buying things that works with 3 things already in your wardrobe & that struck me as v practical too.
We shall see if i can resist the lure of the beautuful for long...!