boots aren't bad, like em much better than the black kiltie loafers. here's a good example, man-- this guy isn't built any better than you, doesn't appear to be better lookin than u, nor did he appear to spend a princely fortune on his clothing
I can't see any reason you should not be lookin just as sharp, but you gotta make some changes in what you keep/ throw out and what you're buyin. Dull shirts, bad ties, and orphaned / outdated suit jackets aren't doing you any favors!
Blazer - Suitsupply | Tie - RLPL (ebay) | Trousers - Howard Yount | Shirt - Proper Cloth (prob $95) | Pocket Square - the Tie Bar | Shoes - Sid Mashburn (ebay) | Trench coat - Club Monaco