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Notes -
It's a classic look so pulling one off requires a classic wardrobe. @SubstantialFrivolity suggests a suit, though I'd go further and say you need a more classic look suit to make it work. A modern slim cut suit isn't going to work as well. I'd suggest a classic American sack suit look like something from Brooks Brothers, though most retailers offer something along the lines of "Traditional Fit". Something double-breasted will also work, but those are also out of style and can be hard to find. Basically, find pictures of guys who look good in fedoras and take a look at what they're wearing. Another thing that's critical to avoiding the negative connotations is knowing proper hat etiquette. Generally speaking, hats should be removed when indoors. This technically applies to all head coverings including baseball caps, but modern customs have slackened to the point where no one pays much attention to this anymore. If you're wearing a fedora, though, you have to abide. Remember, this is a classic look, and it's going to look off unless you adhere to custom. You can leave it on in a public building like a post office or in public parts of buildings like corridors and lobbies, but it should be removed in places like bars and restaurants, and always in private spaces like someone's home or office. A good rule of thumb is to remove it anywhere you'd remove your coat. If I'm meeting friend for drinks it would be odd for me to leave my coat on for the entire evening unless I were outdoors or it were unusually cold in the building, so treat your hat likewise. It's fashion wear but it's also outerwear.
edit - A couple more things. While I spent a lot of time talking about a classic look, don't wear your hat Sinatra-serious with the brim pulled down. I don't wear a fedora often but when I do I usually tilt the front upwards, which means I'm either trying to look like author and humorist Wyndham Lewis or the Dead End Kids. Also, when you remove your hat, it should be held in such a way that the lining isn't visible, which usually means holding it against your chest (if standing) or on your knee (if sitting).
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