Each week Shift editor Amy Odell answers your fashion questions. Write early and often to firstname.lastname@example.org.
I'm going to a Labor Day BBQ with a girlfriend this weekend. I have a fedora that I think is cute with this cute trim of pastel-colore stripes. I never wear it because, you know, who thinks to wear a hat? But I said something to this friend like, "Oh I can finally wear that fedora!" And she said something like, "I can't be seen with you in a fedora." She was kidding, but in that way that you know she sort of meant it. So, will I be the Token Fedora Douche if I show up in a fedora?
No, because if you're legitimately concerned about coming off that way, you're not trying to come off that way, which is the subtext of the fedora outfits that rub a lot of people the wrong way. For example, this rich kid of Instagram:
The fedora is like the cherry on the douche sundae this photo is. The photo is bothersome because you see this Instagram (captioned "Our ride.") and think wow, this was only taken and posted because these people wanted to show off how "badass" they are. No one likes people who try to show off how badass they are, if their only reason for being badass is an assembly of materialistic things (here: a helicopter, her trendy printed pants, his trendy sockless loafers, her hat). Granted, we don't know who these people are, or why they have the helicopter, but the default assumption is that it's not for any admirable reason (say, she sings like Aretha Franklin, or he runs an awesome successful tech company). The default assumption, probably because these two look so young, is that their parents made this materialistic way of being an alleged badass possible for them, that they didn't have to work for it. It's, to many people who struggle or at least work hard for basic comforts, a repulsive idea. The fedora has become synonymous with this kind of look. It's an accessory as seemingly unnecessary as the "Our ride." caption on this photo. It says, "I am trying to be a badass by wearing something totally unnecessary. I am wearing this thing because some God of Hipsterdom said it was cool, and I am willing to TRY to fit into that perceived notion of cool, without trying to write a my own definition of cool. I am taking the definition of cool that was handed to me — like this helicopter."
That said, you can wear a fedora and not give off this kind of vibe. One, don't arrive to the party by helicopter, private jet, or limo. Two, wear it because it's cute and functional (it hides a bedhead, shields eyes from the sun, and protects the face from UV rays). Three, don't wear it with the standard "Look how cool I am" outfit. This means, probably, avoiding studded jean shorts and super high Jeffrey Campbell booties. Instead, try a breezy gingham button-down shirt, jorts and thong sandals. Then, you will not look like a douche. You will look like someone who wanted to be comfortable, cute, and functional instead of someone who was going out of their way to be like everyone else and make a pointed fashion statement via fedora about how good at that they are.
And besides, non-fedora hats can be just as douchey!
But as I always say: if you like something, just wear it. Life is short and difficult and you may as well get to enjoy the fun of wearing a few different hats.