* The Sheriff in ''ComicFuryWerewolf'' typically has a NiceHat. Kristy was the first player to have one.
* The Whitecoat, a SuperHero from ''Literature/TheDescendants'' 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!
* ''LlamasWithHats''.
* Reginald Cuftbert's badass bonnet in ''SpoilerWarning''
* Linkara of WebVideo/AtopTheFourthWall. It's even mentioned as such in his theme song.
** It's also magic, preventing the CastFromHitPoints nature of the Website/ThatGuyWithTheGlasses world from hurting him.
* {{Anti Cliche And Mary Sue Elimination Society}}: Don't touch Stephen's hat if you want to live.
* ''WebVideo/AficionadosChris'' his trademark "beaver cap". It's even mentioned in his theme song.
* [[WarningReadersAdvisory Derek the Bard]] has a really sweet tophat.
* Mayor Conner of Eastwood in ''FalloutNukaBreak'' has a FOOT-TALL TOP HAT!
* [[DiamandaHagan The Minion]] in ''Film/ProjectMillion'' 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 LoadingReadyRun's ''FeedDump'' ends with "[[CatchPhrase There may be better sources for news]], but they don't have]] ''[[CatchPhrase this]]'' [[CatchPhrase 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 ''WebVideo/CommodoreHustle'', possibly at the cost of crew member Jer.
* Rowdy C, host of ''TVTrash'' sports a pretty nice Golfer's cap.
** In his ''Candid With Chris'' videos, he sports a black cowboy hat.
* ''Literature/SkippysList'' has examples:
--> 163. Take that hat off.
* Yahtzee Croshaw of ''WebAnimation/ZeroPunctuation'' wears a distinctive trilby. In ''ZP''[='=]s simplistic art style, it distinguishes him from other characters. In real life he said he wears it less since it started to get him recognised.
* Theatre/TheLeagueOfSTEAM's zombie manservant, Zed, wears a fez. Baron von Fogel and Coyote wear [[DashinglyDapperDerby 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.
* ''Roleplay/EquestrianLegends'' has more then a few nice hats.
* While fenoxo's game can no longer be linked to or referred to directly on the [=TvTropes=] wiki because it's NSFW, it absolutely ''must'' be said that his AuthorAvatar Fenimp wears a very nice fedora.
* ''WebVideo/TheUnusualSuspect'' wore one for most of his early reviews, it has since been replaced.
* In episode 26, [[WebVideo/TheMusicVideoShow The Music Video Show]] wears a skull tuque after several episodes of various plain looking hats.
* In the early chapters of ''DiveQuest'', Muschio comes across several hats that don't really do much for him. Then someone suggests he put on an animal skull, which actually looks pretty respectable. Then, one poster urges him to put another hat on top of it, which he does... then, while he's at it, he puts on the other hat, and then he starts throwing everything he can think of onto his head in sarcastic deference to the voices in his head, including the crystal ball through which they manifest and keep voicing their collective obsession with hats...
-->Mad? I'm not mad! I'm just following your fantastic fashion advice!
-->HERE!
-->YOU WANT HEADGEAR? I'LL SHOW YOU HEADGEAR
-->HOW'S THAT
-->TELL ME WHAT THE VIEW IS LIKE FROM UP THERE
** ...and then his sidekick walks in on him with ''no idea'' what he's doing. ("quick! put her on your head too!") Muschio stammers something about something or something or other, then foists the mess on her, tells her to make a better hat out of it and runs.
* [[Franchise/TheSlenderManMythos The Slender Man,]] in his earliest depictions, wore a black hat.
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