I wear dress shirts, I think i have about 15 different one's, but other than the dress shirts i look homeless, don't shave or get my hair cut regularly. I think for the most part the more flashy and
dressy the clothes are, the more uncomfortable they are. Where I live, I am very under-dressed as a lot of guys wear beautiful suits and dress shoes. I went to Philadelphia a few times the last few years and I wore the dress shirts and stuck out like a sore thumb, it is a working class town, no one other than the hotel employees dressed like that. So it depends where you live, if you live in a rich area, you will stick out more wearing bummy attire.
I also hate shopping for clothes, it has been probably 15-20 years since I stepped foot in a clothes store. I get literally nuts after about 1 minute in a Gap or even Polo store. i hate picking out clothes, i hate discussing colors and sizes, the whole thing makes me mental. No offense to anyone, but i think guys who regularly shop at department stores for new khakis and dress shirts and have fun doing it are either gay or have major problems. I am not saying it is wrong to be gay, I just think shopping for clothes is a very woman thing to do, no offense. I have never seen or heard of a woman who didn't love everything about shopping for clothes, the process, etc. If you absolutely need clothes for work, that is another story. i think a lot of the guys in my town are regularly shopping for the newest styles and they all are thin and work out and eat right, I am the absolute opposite of any civilized 21st century man