jfrater, you seem hell bent on cheerfully spending thousands of dollars so others can voyeuristically watch you crash and burn. You aren't gaining a sense of style (much like an fat person doesn't gain a better appreciation of food gorging at a buffet) because you are simply buying for the pleasure of buying; or worse buying to please others. You have no style, much as you might spend. Men who do don't need to buy at the clip you have, especially based on the advice of others.
At the end of the day you will buy what you want, with whatever fleeting pleasure it may continue to bring you. Or, you will read this post, and take it as it is meant to be taken, which is in the spirit of trying to help you. Slow the fuck down. Spend some time putting together outfits from the ridiculously outsized and expensive clothing and shoes you have. Pay enough attention to what you own to get it tailored properly. Buy shoe trees for every pair you own, not just some of them. You may or may not have a sense of style after a few months or years of this, but as others have posted, you will probably make some better decisions with a bit of time and perspective.
You may or may not follow the advice above or the more politely worded advice that is in a similar vein to what I have read posted since you have begun your recent spending spree. No skin off my back either way, but note that there has been a growing number of posters here that have been quietly appalled by your wasteful spending. It has kind of been like watching an elderly person with dementia shit themselves.