I am always among the well dressed guys in the office. However, for me form and function matters equally. I used to have expensive suits, shoes, tailor made from scratch and it was great for a time but as soon as weight or size fluctuates just a bit, it can get uncomfortable quite well. These days, I still buy rather expensive business clothes but it's not the very high end, more in the medium range and usually not tailor made from scratch. My go to strategy is to buy good looking clothes, shoes and belts and retro fit them to me by a tailor and I make sure to leave a little room when it comes to the fit. Just a little. Still looks great but not as good as a completely tailor made suit. Besides that, 90% of guys don't wear that either so I still look better than most of them. Also, I usually go for a business casual style these days. Combined with chino pants....man, I can wear those pants all day. No discomfort, nothing.
I could wear my business outfits all day without any discomfort. I could sleep in them and I still look better dressed than the majority of my co workers.
I could wear my business outfits all day without any discomfort. I could sleep in them and I still look better dressed than the majority of my co workers.