Honestly, not to sound like a fop, but if you trust yourself to moderate opinions you hear, go for something "old fashioned" like https://www.gentlemansgazette.com/ and learn some of the old-timey rules and then work forwards from there. Like many squishy disciplines, modern fashion is hopelessly complicated with 15 levels of counter-counter-counter-counter-counter-signaling, and going back to the basics can help.

Try to learn things like:

• How do I know if a shirt fits?
• What's the basic mold than men's outfits were built around (hint, it's the suit) and how does the shadow of this hang over modern fashion?
• Why do we care about "clashing" outfits, and how do I know if two pieces of clothing "clash"? What colors go together, what patterns go together, etc?
• What materials exist, and how do I, personally, feel about including them in an outfit?

I often get very frustrated responses when people come to me for design feedback and I respond with things like "well, I think this website is communicating that you are a kind of 90s CS professor? Is that what you want?"

I know you (literally and explicitly, in similar words) say it, but this is also true of fashion and fashion advice; you are choosing what message to convey, not whether to convey one.

In the post it says:

Of course, there are lots of other options besides literally just a leather jacket. As a general rule, any outfit which makes people ask “are you in a band?” signals coolness. Personally, I usually wear all black, including suit pants and jacket from a tailor in Shanghai, Converse sneakers, a black hat, and sunglasses.

I have nothing against John and am not commenting on John. However, there were multiple kids at my highschool who thought they would dress like they were in a band and then they'd be cool. We thought these kids were losers, because they acted like aliens with self-esteem issues looking for hacks that would make them cool.

A different way to think about fashion is to ask "What do I want people to think of me?" and "Who do I think of that way, and how do they dress?". If you want to look cool, you should be thinking of people who are cool and how they pick their clothes, not wearing sunglasses at night^[1].

Just like how websites can choose to look like Facebook or like Youtube or a '90s computer science professor, in fashion there are a thousand ways to look cool and you need to select the appropriate style. Don't dress up in a snazzy suit to volunteer washing oil off of ducks, don't wear your leather jacket to a wedding, and maybe throw some faux-minimalism on your website if you're trying to make it look trendy.

You have to find your niche though! The explicit moral of this comment is have an intended message.

Personally, I would always recommend dressing in high quality clothing^[2] that is conspicuously not trendy (not bad looking, just not stuff that signals having just been bought) and that fits you well. This would be really bad advice for some subcultures!

It doesn't really seem that similar to me at all?

"All illegal drugs should be legal, if you buy them at a special government-managed shop, under the condition that you sign up for several months of addiction treatment."

"Supervised Injection Sites" are missing the bit where you get legal immunity in exchange for locking yourself into rehab, which is the core of the idea. The idea isn't just "there should be a place where you can do drugs without being arrested", or even the (really cool) idea "there should be a place where you can do drugs with medical attendants". The idea is "drug users have messed up discounting rates, can we legally lock them into rehab using their drug cravings?"

I think that's a really interesting point^[1], but a really unhelpful (in the "Ways that Words Can Be Wrong" sense) way to interpret the exercise. It would remove some of the creative potential from the medianworld concept to interpret it as a list of traits about cavemen.

Is there a download API? I'd love to download posts as Markdown if that's already built-in. (Eventually, I'm working on integrating this into a tool which helps me make PDFs for my e-reader or for printing out with custom formatting).

The next thing I noticed was that I was the butt of half of my jokes. I'd keep thinking of zingers which made me out to be a loser, a moron, a scrub in some way. Sometimes, I could re-work the joke to not insult myself. Often I couldn't. Self-mockery served as a crutch for me. 

Well-meaning note to people who do this a lot: what you think of as a 'zinger' is frequently not very funny and is just a self-insult. This post calls them a "crutch", but crutches trade off atrophy in your legs for letting you move around. For many people self-deprecating humor is more like digging a hole and lying in it: your normal humor atrophies and you're not funny while you're using these.

Props to OP for getting off this thin humor and onto the good stuff :)

This reminded me of Zvi's "Levels of Friction", but it's not the exact same idea. Comparing the two essays and how they think about this is sort of interesting though.

Suggestion: naming the account "Duncan (crossposting)" or "Duncan (not reading the comments)" might lead to less confusion.

I have been confused several times by Duncan's posting and commenting and assumed it was just normal some normal human grappling with a vice stuff. If it really is meant to be about commenting or something, I want to flag that this is not getting across for me or anyone I've directly discussed a Duncanpost with (who has mentioned the username).

I said similar elsewhere, but I agree that "I" speak would be really bad (don't put words into the author's mouth, especially in this case, where it would mislead the reader about the writing style/ability of the post), but I also think switching out the post for a summary is pretty jarring to begin with.

Since every post for years has been peekable as the first couple paragraphs, showing a summary unlabeled is always a jarring bait-and-switch

Ah, so it really was an AI summary of a post that is totally unlabeled? An amusing twist.

Even with what appears to be a fair amount of fine-tuning, it still reads like unlabeled AI text, which is maybe why I found it so jarring. Possibly a label could help, then?

(though honestly, it's pretty weird to not see the first paragraph, so even if the AI thing doesn't ring as important to you, some kind of differentiating label would be REALLY HELPFUL when the expected POV is altered after the fact.)

(RE parenthetical: I heavily suspect you know this, but switching the POV to first person would be much much much worse and would lead me to skip posts I would assume read like AI text)