@Zennistrad Heh, I’m the opposite way. I LOATHE people who just do a t-shirt and nothing else. It speaks to me of a lack of commitment, and then I start to wonder if I can really depend on them for anything at all. The type to wear random franchises/band logos as t-shirts, especially here, tend to be potheads or college kids, so it winds up a pretty accurate stereotype. Alternatively, if they have like 20 bits of ‘flair’ all from different shows, and especially if those shows are all wildly different, I have to wonder if they’re just trying too hard or are maybe really confused. TMI/information overload can be just as bad as revealing nothing at all.

I think most of the backlash against fedoras just comes down to how the people who wear them choose to present themselves through how they dress.
 
I have a friend who’s pretty much the stereotypical brony: he has a trilby and carries around an MLP backpack. The other day he showed up to our usual social gathering with an MLP belt and a chain necklace with at Twilight Sparkle figurine at the end.
 
While I don’t think it’s particularly fair to judge by appearances alone, his outfit seems to demonstrate a general lack of any fashion sense as well as a borderline-obsessive interest in the show.
 
That, in effect, is where I think the backlash against fedoras (or trilbies, if you insist on being pedantic) lies: they’re worn by people who have no idea how to wear a hat in a way that doesn’t visibly clash with the rest of their outfit. They’re worn by people who wish to be “stylish”, but have no idea how to develop a personal style.
 
A personal fashion style should, ideally, make a statement about yourself. One of my other friends, for example, has mutton chops and often shows up in Victorian-era dress. This outfit tells you right away what he’s like: he’s very interested in 19th-century history and culture, and has a general air of formality about him. Even dressing casually makes a statement: it says that you’re honest about yourself and that you don’t particularly care about how you present yourself to others.
 
But the people who wear trilbies like this are at sort of an awkward middle ground between dressing casually and having a personal style: they care enough to try to appear stylish, but they don’t quite care enough to put in the effort of making it really work. The statement this ends up making is that they lack the confidence to actually commit themselves to improving their appearance. It’s understandable why they might not make the commitment: trilbies are meant to be worn with suits, and the rest of a suite is very expensive compared to the $10 hats you see at Wal-Mart. But if you’re not going to at least try to make it work, you probably shouldn’t be wearing the hat at all.
 
When paired with a bunch of MLP clothing or accessories, it only becomes more awkward. My Little Pony, as good as it is, is just a TV show, and to wear so much licensed clothing or accessories at once gives the impression that the show is your identity. We’ve all seen the “creepily obsessive fanboy” stereotype in our lives, and there’s a reason it has such a stigma: to be so obsessive about something that doesn’t really exist makes it look like you’re oblivious to the real world. You saw the same thing with Trekkies back in the day: they were ridiculed because they spent so much time in their little sci-fi world that they didn’t appear to care about anything else. That’s why, if I ever wear anything related to an anime, video game, or cartoon I like, I try to keep it to no more than just a t-shirt.
 
TL;DR How you dress leaves a fairly large impact on how strangers perceive you. If you wear clothes that don’t look good together, or are overly focused on a single media franchise, it doesn’t leave a good impression. It’s unfair, certainly, but people are never going to stop judging by appearances since nobody has the capacity to know every single person on an individual level.

Trilby…fedora…both marks of the same neck-bearded beast.

@Background Pony #384C  
Maybe that’s why he’s actually wearing a trilby, and not a fedora.

Though points for not doing hover hand.

With how fedoras’ reputation has gotten, I wonder why people still wear them.

Oh I know that guy, back in my childhood he used to make these Thomas the Tank Engine videos that now that I look back at them, were pretty stupid but he moved on from those. He’s a good video maker regardless anyway.

downvote because Fedora doesn’t make you a manly man

That EQG cosplay of Trixie is pretty good.

..Wow
 
She’s so tiny
 
or that guy is really tall and lanky

@Background Pony #C13E  
M’la-  
Gets shot

>inb4 le fedora maymay