Originally Posted by SoCal2NYC
Tuck in your shirts. Buy your jeans a size smaller. Have your jackets taken in and tailored. Buy non-Platypus bill toe shoes. Learn to make a smaller knot.
+1. That would at least get him started. A better haircut would help, too.
But, overall, Mt. Spiffy, just because you "intended" for your outfits to look like that doesn't and isn't going to make them look any better, nor is there really going to be any way of justifying it that doesn't still make them look ridiculous. The industry in which you work is no excuse either; if you are intending to look "fashion forward" this ISN'T the way to do it.
In short, what exactly ARE you intending to do with your outfits? You aren't flattering your body style; they are so ill-fitting your body shape disappears beneath the clothes. You also aren't hiding your problem areas while accentuating your goods; you are simply drawing attention to yourself with a garish outfit. Are you attempting to create a new "style" that will make you unique; if so, nevertheless you are dressing virtually like 90% of the other people who simply don't understand the first thing about dressing and just grab something out of their closet and wear it.
In short... I don't really see the point. But, of course, you obviously have confidence to post yourself on a general forum. So, as SoCal mentioned, you aren't hopeless. With that confidence and a little more concern about fit and "mixing," it could work.