And you've already received a ton of great advice. The Alden long wing in #8 shell, or a nice Alden style boot would be perfect for what you want.
They're shoes. This is either a terrible case of paralysis by analysis, or you're just bs'ing. Again, they're shoes. Buy some you like the look of and see if they fit. There's no perfect shoe for wear with your blazer, jeans, and t shirt.