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I guarantee you that those $500 shoes will not last one whit longer than a good $90 pair of shoes. So what is the point? Yeah you can resole them, but they won't bu significantly resisting to damage to the uppers. I can resole the $99 shoes too. As for them not stretching, the hell they won't. Knowing when to order a size larger, smaller, or ture to size means you have to understand the US foot measuring system, your foot, the general last shape the shoe was made on, if it was a US , european, or asian version of that last, and the material. Buying bigger is ALWAYS a mistake unless you are simply talking by number. Try them on for fit. Do not buy larger. You'll get blisters, or at least have unhappy feet.

And you still have to understand fashion to some extent. You can follow all his advice, and wind up looking VERY dated, stodgy, or anything BUT low key and presentable. Running around in a seersucker jacket sends a huge message, contrary to his opinion. That message is not low key, or generally well received.

Also, a good tailor is worth his weight in gold. You can have a nice suit, but if it isn't tailored right you'll make it look cheap. Period. If you are going to drop $400 or more on a suit, drop the extra $60 or so to get it tailored RIGHT. It'll make a $500 suit look nicer than a $1000 suit off the rack.

Then there are ties.. they vary significantly with fasion and will date your outfit quickest. Unless it is formalwear, a bowtie always says "hey, there's something deeply wrong with me." So don't wear them, just don't. Just look at the author's picture at the bottom, and tell me that isn't so. Seersucker, a bow tie, and don-johnson stubble. That does not say to me that he has his shit together. Taking sartorial advice from someone like that strikes me as a real bad idea.

Also, I don't know what thrift stores he shops at, but you aren't getting off that cheap unless the clothes are 5-10 years old, or over 25 years old, and peeled off the back of a corpse. Basically it has to be outside the sweetspot for nostalgia and otherwise undesirable compared to something new but cheap.

As for socks, yeah.. patterns are bad. Don't wear argyle, unless your style is screwed up enough that you'd wear a seersucker jacket, a bowtie, and maimi-vice stubble. Argyle would go perfectly with his picture down at the bottom. Probably with ofverly cuffed pants with no break that ride up like floods when he crosses his legs. EWW. Hell, I can picture him happily wearing an argyle sweater vest come chilly weather. Double EWW.

If you want to go stylish with socks, they should be of a color that matches with one of the colors in your other accessories rather than the suit or shirt.

As for his argument against dressing for function, it shows he understand modern mainstream fashion, especially for men, not at all. Unlike the good old days we do not have our functional and presentable time as casually divided up. In the end, function wins. Largely due to replacement costs. A properly tailored suit and a shirt with a good collar make dressing up as comfy as siting aroun in some nice pyjamas. But the durability is for shit and replacement costs are high.