Nice Hat/Web Original

The Sheriff in Comic Fury Werewolf typically has a Nice Hat. Kristy was the first player to have one.
The Whitecoat, a Superhero from The Descendants rocks a white stetson so nice that people think it's somehow part of his powers. They would be right, because he's got a vid screen with a heads up display under the brim!
Llamas With Hats.
Reginald Cuftbert's badass bonnet in Spoiler Warning
Linkara of Atop the Fourth Wall. You know it's true.
- It's also magic, preventing the Cast From Hit Points nature of the TGWTG world from hurting him.
  - It's even mentioned as such in his theme song.
Anti Cliche and Mary Sue Elimination Society: Don't touch Stephen's hat if you want to live.
Derek the Bard has a really sweet tophat.
Mayor Conner of Eastwood in Fallout Nuka Break has a FOOT-TALL TOP HAT!
The Minion in Project Million looks too conspicuous with her mask, so Hagan makes her switch it to a top hat with Mickey Mouse stuffed through the middle. It's still big enough to cover her entire head.
Every episode of Loading Ready Run's Feed Dump ends with "There may be better sources for news, but they don't have this hat." The hat changes every time. This probably stems from the "sweet supply of hats" that LRR has collected over the years - the hats which Graham sought to protect in Commodore HUSTLE, possibly at the cost of crew member Jer.
Rowdy C, host of TV Trash sports a pretty nice Golfer's cap.
Skippys List has examples:

163. Take that hat off.

Yahtzee Croshaw's famous trilby.
The League of STEAM's zombie manservant, Zed, wears a fez. Baron von Fogel and Coyote wear Dashingly Dapper Derbies. Sir Conrad, Jasper Mooney, Professor Jager and Mrs. Potts wear top hats, Ellie Copperbottom wears a mini-tophat, and Thaddeus wears a boater.
Equestrian Legends has more then a few nice hats.