Look at this if you are planning to wear/buy any type of hat besides a baseball cap or a plain wool winter hat (you think those people look good?). Wearing a fedora or similar hat isn’t a silver bullet to classiness or fashion. It does the opposite, actually, and you end up looking like a try-hard dickhead. If you absolutely must wear one you better be wearing a full suit to go with it. As one MFAer (sorry if it was you and I don’t remember your name) commented before on this topic, it’s like wearing a bowtie with a t-shirt. 90% of your outfit is fine, but more importantly it is a very casual one, and laid back. But when you put on the bow tie in this analogy, your whole outfit goes to shit and looks ridiculous, because of the mish-mash of the formality of the pieces of your outfit.

• “But DammitMcNulty, people comment on my fedora all the time!, so they must love it!” False. Just because someone acknowledges your hat and comments on an item you are wearing doesn’t necessarily mean they like it, it just means it stands out a lot, and is out of the ordinary, and are using it as a point of conversation. Even if you are wearing a goddamn top hat with a t-shirt people will comment on it to you regardless of how they think it looks, most likely negative. It’s just something people do when something stands out. Just like the way people don’t talk about normal weather at all, but when it suddenly rains or there’s a drastic temperature change, it hence becomes out of the ordinary and something to talk about.
• “You can’t tell me what to wear, I don’t care what you think, I think fedoras are still made of win” Don’t say I didn’t already warn you, because this is what you look like.

Just don’t go near those kind of hats. Unless your name is Frank Sinatra, Humphrey Bogart, or Don Draper, that is. And if you’re going to get mad at me regardless for this, well you came to /r/malefashionadvice, for male fashion advice, right? This is a place where you will get advice and get items/outfits critiqued, and not a place where everyone is going to jerk you off regardless of how you look.

EDIT: Never said bow ties look bad- just used the analogy of wearing a bow tie with a t-shirt to compare with how a lot of people wear fedoras. And a fedora, trilby, panama, WHO THE FUCK CARES, they all look bad on 95% of people.