Man I feel like a looser. Jeans, a plain t-shirt, rainbow flip flops and I'm good to go. The flip flops probably cost more than the jeans and the shirt.
I'm with you.
I consider my style to be "no style" (like Bruce Lee). I'm into ultra casual.
Jeans and a button front shirt - flannel in the winter, cotton in the spring/summer/fall. My physique (or lack thereof) doesn't really permit me to wear t-shirts or anything pullover.
In the winter, I wear Land's End squall boots for shoes because of the snow, ice, and general slop. In the summer, Sperry Topsiders or blue Rockport boat shoes. I did score a couple of pairs of Lacoste sneakers on closeout to wear this spring/summer - after the snow melts and all the winter slop dries up. I have a pair of Chaps sneakers for dog walking and dog park (machine washable if I step in you-know-what).
I've been able to get by without wearing a suit for a couple years. Now, I only wear them to weddings, funerals, and Bar Mitzvah's.
Back in the day, when dress up was required for work, I wore suits, ties, had a different set of braces for each suit, custom tailored shirts so they would fit decently (as I'm in between standard sizes), and enough dress shoes to never wear the same pair more than once a week. It was nice, but I'm much more comfortable these days and I have money to spend on RAD, SBAD, SSAD, and SCAD.