Maybe a madras jacket doesn't work (for us in the UK, don't know about US) because they scream for attention? Whereas I think most other things we like to wear tend to be under the radar (to the average Jo)? If your everyday tastes tend towards muted knitwear, chinos loafers etc. a madras jacket is actually a pretty big leap.
Also, I suspect a lot of us are comfortable dressing to please ourselves, rather than attracting attention from others? It's difficult to imagine my mates down the pub applauding my choice of chinos. Or mums on the school run going week at the knees at the sight of my collar roll. And I like it like that.

Yes, I think farrago said, quite some years ago, that even the wearing of a Shetland sweater drew remarks on being 'dressed up' (in his part of America).  People near me - male - look like they might have been dressed by Stalin in preparation for the gulag.

Back in the days when I used to wear ties, ladies would play with them.  It's an act of foreplay.  I mean, you might not get laid there and then but it's on the cards.  It's exactly like when they steady your hand when you light a ciggie for them.

Yep.  Scruffy.  I'm a great people watcher.  If anyone bothers to stand out it's almost always a young female, doing her own thing.  Even that is a rarity.  When did men cease to be sharp?  My father - a fair dresser in his day - stopped bothering after retirement.  I was amazed at what I found in his wardrobe (aside from a collection of very interesting DVDs - made my wife turn quite pale): stuff he'd evidently brought back from his Stateside trips and never worn.  Back in the day, of course, he never went tieless.  Look at old movies like 'Hue And Cry': Harry Fowler and his mates in bomb-wrecked London.  Smart turn-out.  Clean living under difficult circumstances.

Unfortunately I was too low down the pecking order for it to be a serious proposition and her main targets were the partners of the practice.

One of the girls in a 'vintage' shop I used to frequent did not know what was meant by a button-down.  She thought it was simply a shirt that had buttons.  Not the sharpest knife in the drawer. 
My daughter wears a belted trench coat, often teamed with a beret.  I wear fly-fronted macs.  Mac - raincoat - where's the difference?

Whilst we are the subject of dodgy descriptions; another inadvertent or deliberate error is listing women's jackets or coats in the men's coat category. This seems to happen a lot with lesser known labels like Grenfell and Invertere. I think they are often just chancing their arm and hoping someone will buy it, then be too embarrassed to return it, or even not notice that it buttons the wrong way.

My worst EBay experience was being blatantly ripped off by a UK seller.
I purchased some John Simons frog mouth tweed trousers. Really lovely looking and I can’t recall seeing this grey version in the store.
Advertised as a 36??  waist but when they arrived they were no bigger than 32??
I contacted the seller but he simply pointed out they were sold as no returns.
He obviously knew they were considerably smaller than the tag but choose to write off his costs by passing the issue down the line

Etsy was better.  At least when it first started.  Mostly nice young women who would attach notes and little free gifts.  I still treasure my Harvard key-ring (which I flashed at the girl on the gate at the American Embassy, hoping she'd let me jump the queue for my visa application; she didn't.  Jesus, has anyone been inside that place?  Like a big fucking DHSS building, staffed by the CIA).  I don't suppose it cost more than the price of two portions of chips but I love it.  A little bit of 'Ivy League' in the right hand pocket.