The examples I've picked are all modern day staples of what the average man wears on a daily basis. We have come a long way from the days when a suit was the default choice of clothing for most men. It still survives as daily wear for some white collar professions and dressy events but it's days of being daily wear for most have long passed. What we do have is a more casual world and one in which various garments of sporting and military origin have been pressed into service as practical, every day wear. Sure, you can wear them badly but there are plenty of skilled dressers who wear the examples I gave and look a long way from 'ridiculous'.
Denim jeans: Originally for rough manual labor, and that's about the only place it looks good. Working in the garage? Giving a talk on a stage? Tells the audience you are a scrawny white guy trying to be "cool", and/or going through midlife crisis.
Here's SF's own Gerry Nelson wearing them with a naval pea-coat - do you think he looks like he's going to be doing manual work/within a stones throw of a ship/in the throes of a mid-life crisis?
This makes no sense. A polo-shirt is fine at a weekend cabin but changing the context makes the wearer look like his mother shops for him? A polo may or not be appropriate for office wear depending on the dress code but saying that they look 'nerdy' is ridiculous. Simon Crompton's rig below of a Smedley polo and trousers would make a very nice outfit for a casual office or Friday wear.
Button-down collar oxford shirts were conceived in an age where men wouldn't have dreamed of not wearing a tie with their shirt. The collar was designed to be worn with a tie.
Sports jackets come in a multitude of colours. There's nothing particularly 'countrywear' about say, a blue window pane jacket with grey flannels, nor does a jacket with jeans make the wearer look like a self-concious hipster.
I would strongly suggest that you consider removing your head from the rectal passage and get over your preconceived notions about clothing usually only looking good when worn for it's original purpose.