What's the difference between these 3 images? Why is one the ubiquitous example of great style, another the joke everyone wants to avoid becoming, and the last what your typical guy looks like?

I'll explain.
Great style consists of two things - positive aesthetics and cultural relevance.

Positive aesthetics simply means it has to look good - it should follow the rules of proportion and symmetry, the colors should be flattering, etc.
Positive aesthetics are why we love period pieces and classic old style.

The clothing visuals we love are those that are pleasing to the eye and give us a sense of satisfaction while looking at them.
But positive aesthetics aren't enough.

You can't throw on a toga, or a kilt, or a 19th-century 3-piece suit and walk around in it today because, as beautiful as the aesthetics are, there's no cultural relevance.
This is the biggest mistake the gentledorks make - all aesthetics, no relevance and it's actually why most of the guys you see doing period dress are culturally insignificant guys with no social status or standing.
On the other hand though, there are plenty of situations in which cultural relevance becomes critical - and then overplays its hand.

This is where most trends come in.

Aesthetics are thrown out the window and a goofy, exaggerated version of relevance takes shape.
This is also why we don't look back on trends fondly but cringe when we see them.

Once they've been stripped of their relevance, it becomes even more obvious that there was no inherent beauty or aesthetic to them and we wonder how we could ever have thought it looked good.
Trends don't look good. They look high status.

So great style is a combination of both.

You have to both understand aesthetics well enough to make your clothing look good, and your culture well enough to make your clothing relevant.
So why do most guys go this route?
Because they don't know how to do either and the risks of trying and failing are too great.

So, rather than play to win, they simply attempt to not lose.

Rather than choosing clothing that's beautiful, they get stuff that isn't ugly.
Instead of having a style that's culturally relevant and signals some social fluency, they buy stuff that doesn't look irrelevant or out of date (or so they think).

Rather than risk standing out in a bad way, they do their best to simply fade into the background and simply exist
The principles of great style aren't that hard - combine solid aesthetics with cultural relevance.

And even the execution isn't that difficult once you know what to look for and how to make it happen.
If you want help with that, and are sicking of merely playing not to lose, let's talk.

https://masculine-style.appointlet.com/s/coaching-exploration
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