There have always been different levels of attire. A construction worker has always worn different clothes than a banker or a solder. This is because clothes do more than cover our nakedness. They also serve functions and each style can look good in it's own way if the fit is right.

In my job (truck driver) I have to feel comfortable sitting for many hours a day as well as be able to climb up into the cab of my truck. So, I buy my clothes with that in mind. I wouldn't be comfortable in a three piece suit and tie. So, I wear denim or khaki pants with cotton T-shirts and have a leather jacket near by for cold and rainy days.

My shoes must be easy to clean, give me a sure footing on greasy surfaces and again be comfortable while I'm driving. A soft moccasin does the trick most of the time. But I do keep a pair of boot handy just in case.

I keep my colors simple so everything I wear matches with everything else.

So, I think it's not so much about what a person wears, but about how they wear it that makes it look good or bad.

People here have been doing that for the last few years...once when the temp. hit the 80's in Fahrenheit, I came to work in shorts and a tank top, similar to all the ones like women wear, and was told to go home and change the top...Wtf??? Must have been because I didn't have boobs; so much for gender equality in the workplace. I have some designer label loincloths, like Ralph Loren, Gucci,Giorgio Armani, etc. and come hot weather, I'll try those or save them for the annual Naked Bike Ride Day here; a huge event in many cities:laughing(and yes, lots of people work that day and do ride to work... )
If your city or town doesn't have a Naked Bike Ride Day, they really should...