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dlthomas comments on A Rational Approach to Fashion - Less Wrong
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Why is a fedora "excessive"?
http://suburbantragic.tumblr.com/post/4012562140/someone-finally-said-it
What he bought and what he is wearing are two very different hats. Real fedora versus short-brim fedora, to start with - and the pin stripes take it to an additional height of ridiculous.
Edited to add:
Also, this pretty clearly makes the case that some people look fantastic in a fedora.
I never said there were people who didn't look good in a fedora. But it is a really good illustration of an accessory that people try to wear because some people make them work but fail again and again. There are certain people and certain contexts where it works-- but a beginner to fashion should not look and Bogart or Timberlake, see their hats and try to add the hats to their wardrobe.
Ditto cloaks, unless you already look like Glorfindel or similar.
Contrasting this with
How do we know what's too difficult for a beginner? Must we observe lots of people who strike a very good impression, and only seek items which are similar across the majority of the training set?
This may work, but not (I think) as well as looking for failure modes of an item you wish to adopt. Who looks bad in it? Who looks good in it? Can you find why? Which is more likely to be you?
Not to mention that there are... confounding uncontrolled variables at work.
Yes. Shave him, put him in a suit and tie with a trench-coat over it, and give him a real hat, and he won't look like Bogart but he will look worlds better!
Edited to add:
Though of course possibly still silly, depending.
Do you consider yourself ready to bring "sexy back"?
I mean, just look at the photos in that first link. The man looks ridiculous.
I am totally ready to bring sexy back, just... not by dressing like Timberlake.
Short-brim fedoras are usually silly, but I wear hats regularly (two fedoras and a panama in my rotation) and I regularly get complements. His biggest mistake is wearing that much black during the day, though.