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How do I pull off a casual Fedora?

People tend to forget that back in the day the fedora was an everyman hat. You could wear one with overalls as easily as a suit. They aren't really dress hats, just hats. If you want a dress hat, get a homburg. If you want a hat you can wear with anything, get a fedora.

Leo
 
Something like this

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or this

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bah, go milan
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I know a lot of men are getting interested in Fedoras now days, but to get by with a casual fedora you must:

1. Have a small head / slender face
2. Look like Humphrey Bogart
3. Dress like you live in the 1940's

I am just kidding, I love the look of the fedora. I am only sorry it is not for me.
 
Confidence.

Yup.
However there are different types of casual fedoras. There are the ones in your detective picture and there are the kinds that Kangol makes. I prefer the Kangol ones cause they work better with a younger guy look (dark slim denim, nice sneakers not some New Balance running shoes or something, nice sweater or shirt with a bomber style jacket). The Kangol ones are a balance between the old school ones you like and the annoying hipster fedoras that all the stores sell now.
As for your question, I'd suggest a coat that has a similar cut to that trench coat regardless of its length with some khakis like you said. As for shoes, I'd think either something that is intentionally not a dress shoe or a nice brown dress shoe. Nothing with a clunky square toe, but not one of those super pointy modern shoes either since those are really more for guys who are going out at night and wearing jeans in my opinion.
If it's cold enough, I'd suggest a solid collared shirt with a v-neck sweater over it. Perhaps a nice scarf to top it off, or not...and a spray of Blenheim Bouquet underneath it all. I think that'd be pretty classy
People will probably disagree but that's what I think.
 
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