I'm mostly oblivious to fashion. The other day I put on a pair of pants that I hadn't worn for some time. My wife looked at them dubiously. "Do guys still wear pants with cuffs and reverse pleats?" she asked. "They did in 1990," I said, after a bit of calculation. Oh, well.
It turns out that I do pay attention to what the fashionable man wears, though, sometimes. In novels. When I settle down with a book to escape the pressures of everyday life, part of imagining a different time and place comes with the observations the novel's characters make about how people dress. For example, a hat:
“This hat is three years old. These flat brims curled at the edge came in then. It is a hat of the very best quality. Look at the band of ribbed silk and the excellent lining. If this man could afford to buy so expensive a hat three years ago, and has had no hat since, then he has assuredly gone down in the world.”
“Well, that is clear enough, certainly. But how about the foresight and the moral retrogression?”
Sherlock Holmes laughed. “Here is the foresight,” said he putting his finger upon the little disc and loop of the hat-securer. “They are never sold upon hats. If this man ordered one, it is a sign of a certain amount of foresight, since he went out of his way to take this precaution against the wind. But since we see that he has broken the elastic and has not troubled to replace it, it is obvious that he has less foresight now than formerly, which is a distinct proof of a weakening nature. On the other hand, he has endeavoured to conceal some of these stains upon the felt by daubing them with ink, which is a sign that he has not entirely lost his self-respect.”
[The Adventures of Sherlock Holmes, Arthur Conan Doyle, 1892]
I can't imagine drawing comparable conclusions about a modern baseball cap, but then I'm not Sherlock Holmes. Fortunately, I can guess what kind of hat Holmes was examining, even if men's hats went out of style a half-century ago. Sometimes, though, I'll have a little bit more trouble. What's a mess jacket?
“Yes, Jeeves?” I said. “Something on your mind, Jeeves?”
“I fear that you inadvertently left Cannes in the possession of a coat belonging to some other gentleman, sir.”
I switched on the steely a bit more.
“No, Jeeves,” I said, in a level tone, “the object under advisement is mine. I bought it out there.”
“You wore it, sir?”
“Every night.”
“But surely you are not proposing to wear it in England, sir?”
[Right Ho, Jeeves, P. G. Wodehouse, 1934]
Absolutely! I suppose. If, like me, you're not familiar with civilian versions of articles of military dress uniform in the 1930s, I've discovered that a mess jacket looks like this:

One can see why Jeeves was concerned. The civilian mess jacket apparently had a very short period of popularity; it is not especially flattering to the average male physique. (Jeeves makes judgments based on general aesthetics rather than personal appearance, though, steering Bertie Wooster away from such excrescences as purple socks, red cummerbunds, and the like.)
Not all literary observations about clothing are so innocuous.
"Aziz was exquisitely dressed, from tie-pin to spats, but he had forgotten his back-collar stud, and there you have the Indian all over; inattention to detail, the fundamental slackness that reveals the race."
[A Passage To India, E. M. Forster, 1924]

Beware the missing back-collar stud--it can lead to the condemnation of the character of a billion or so people.
Invidious fashion judgments are not unusual in literature. Consider the waistcoat:
These two individuals were followed by a lieutenant on half-pay, or, to speak more correctly, a retired sutler, who, being the worse for drink, made his entry laughing most indecently at the top of his voice, and, "just fancy!" without his waistcoat!
[Crime and Punishment, Fyodor M. Dostoevsky, 1866]
The necessity of a waistcoat wasn't limited to Russia:
To-day, however, he declined that relief, observing that he had already had too many public details urged upon him; but he spoke more cheerfully than usual, when Dorothea asked about his fatigue, and added with that air of formal effort which never forsook him even when he spoke without his waistcoat and cravat--
[Middlemarch, George Eliot, 1871]
I half-feel the urge to track down a waistcoat for the next time I appear in public, to ensure that I'm taken seriously. What should it look like? This:

I say. That's a bit too formal. Maybe just an ordinary shirt from my closet (hanging next to my ancient pants)? Not so fast:
I had learned that Falk was way up. He was a senior member of one of the oldest and solidest investment firms and sat on eight boards of directors. He had a wife and three grown-up children, and he and they were also solid socially. Evidently a man the race could be proud of, and from personal observation the only thing I had against him was his buttoned-down shirt collar. A man who hates loose flaps so much that he buttons down his collar should also button down his ears.
[Please Pass the Guilt, Rex Stout, 1973]
I give up.


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This is a fun post . . . I had always wondered what a waistcoat was . . .
I was in a thrift shop just this past weekend--and you're talking to a guy who keeps a pair of pants for 20 years, through three household moves. :-)
Thanks for all the comments. (I like all the writers that I've quoted above.)
(A literal reader, someone after my own heart.)
and what's so wrong with purple socks, & red cummerbunds?
As for purple socks...
[I]t so happened that there was a slight estrangement, a touch of coldness, a bit of a row in other words, between us at the moment because of some rather priceless purple socks which I was wearing against his wishes...
He started to put out my things, and there was an awkward sort of silence.
"Not those socks, Jeeves," I said, gulping a bit but having a dash at the careless, off-hand tone. "Give me the purple ones."
"I beg your pardon, sir?"
"Those jolly purple ones."
"Very good, sir."
He lugged them out of the drawer as if he were a vegetarian fishing a caterpillar out of the salad. You could see he was feeling deeply. Deuced painful and all that, this sort of thing, but a chappie has got to assert himself every now and then. Absolutely.
:-D
I would not worry about fashion illiteracy. You seem to know quite a lot.