A fedora, while jaunty when worn right, comes with so much negative cultural baggage at this point in time that you’re best off leaving it alone, along with flare pants and wide lapels.
If you need a little more background on what happened to this poor hat, Vice’s History of the Fedora should help you get up to speed. An excerpt:
While the fedora was enjoying its brief re-entry into the realm of the fashionable, a writer named Neil Strauss was hard at work on what would become the foundational text for the fedora’s terminal phase. In his book The Game: Penetrating the Secret Society of Pickup Artists, Strauss described the “seduction community,” a loose group formed online and IRL by nerdy, socially awkward–and often white, middle class, and entitled–heterosexual men who gave money to self-styled “pickup artists,” or “PUAs,” in hopes of learning how to manipulate women into sleeping with them. Among more nefarious tactics like “negging” and “cat-string theory” was “peacocking“: “a technique developed to get attention in busy, distraction-filled environments such as night clubs…by wearing something showy like a cowboy hat or a glowing necklace.” Many men took this as a cue to wear a hat. Many of these hats were fedoras. In a paper titled “Fedora Shaming as Discursive Activism,” Ben Abraham pinpoints a widely reblogged tip from a popular PUA forum:
“If you wear a hat, make it memorable, easy to spot, and something to work with your style. This is usually easier than it sounds. Try the fedora…it portrays you’re a stylish man that knows what he’s doing, and it’s a great lock-in prop.”
This was both a reflection of pre-existing fedoras and a catalyst for fedoras to come. An infinite feedback loop; a douchebag ouroboros.