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Where'd you get the derby Where'd you get a hat like that If I told you why would you tell me where I could find a hat like that."
Roger Miller, "The Hat"
Country Music Legend Minnie Pearl with her trademark hat-with-price-tag-hanging-down. "Hoooooooooooooowdyyyyyyyyyyyyyy!".
Jay Kay, lead singer of British funk/soul group Jamiroquai, frequently employs Nice Hats during his live shows.
LL Cool J. His Kangol hat is "like a shark's fin"!
Jonathan Coulton's coonskin cap, a la Davy Crockett.
This video. Enough said.
Former Guns N' Roses and current Velvet Revolver guitarist Slash is almost never seen without his trademark top hat.
In fact, Slash's hat has become so iconic that according to Marshall Amplification, if you see a top hat with a Gibson Les Paul or Marshall Amp, you immediately know it's Slash. The man himself is less iconic than the hat he's wearing!
Guns N' Roses' latest addition to the lineup, DJ Ashba, also wears a pretty cool hat. Which he designed himself.
Daft Punk are never without their Cool Helmets.
This Trope plus Rap times Spinal Tap equals Fear of a Black Hat. Niggas With Hats are never without some kind of sick headgear.
Ray Stevens considered it as the ultimate route to fame in country music in 'You Gotta Have a Hat'; ultimately, he gave it up.
Devo's Energy Domes, originally modeled somewhat after ziggurats (not to be mistaken for flowerpots, lampshades, or pet dishes (Jerry Casale still offers a reward of 1000$ to anyone who can find a flowerpot in that shape that predates the Energy Dome)).
One-man band That One Guy, who gets bonus points for wearing a nice hat on top of another nice hat.
Pick ◊ a ◊ Pet Shop Boy. Any ◊ Pet ◊ Shop ◊ Boy. ◊
Taiji Sawada, bassist of X Japan and now of The Killing Red Addiction, and his cowboy hats. Now he alternates between a cowboy hat and a hoodie.
For a time in the 1960s, Michael Nesmith was never seen without his wool hat. By the end of the decade, he could no longer stand the sight of wool hats and hasn't worn once since, though he later began wearing some cowboy hats.
Buckethead's KFC Bucket-hat.
In the late 1980s through the mid-1990s, there was a swarm of so-called "hat acts" in Country Music, many of whom followed the example set by George Strait of wearing pressed shirts, jeans and cowboy hats. Some actually fit well into that image and did not seem to be following the leader (e.g. Garth Brooks, Alan Jackson, etc.), while others were blatantly derivative. Come the end of The Nineties, "hat act" was largely a derogatory term in the genre.
TLC sported an impressive variety in the early '90s.
Lady Gaga seems determined to have as many improbable hats as possible. To the point where her entire head is sometimes hidden by her headgear when she looks down.
Doctor Steel is often seen wearing a top hat when he isn't in his mad scientist outfit.
Former Van Der Graaf Generator member David Jackson is probably just as known for his military style hat ◊ as he is for his saxophone playing.
You might recognize him by his star-shaped shades, but have you ever seen Bootsy Collins without a hat?
The Reni Hat 
U2's The Edge. Bono as well, sometimes.
Nick Mason from Pink Floyd, during the band's post- Piper, pre- era.
Dark Side Guniw Tools's vocalist Full usually appeared in music videos and photos sporting one of his array of bizarre but gentlemanly hats.
Namgar usually wears a Nice Hat at concerts to emphasize her Buryat heritage. Her most famous hat is a gilt and jeweled cap with a Siberian Ibex on top ◊, but she also wears a pointed Buryat hat ◊.
Dome, the ( main) side project of Wire's Gilbert and Lewis, gained a small degree of notoriety for their outlandish stage costumes, particularly their enormous ◊ tubular hats. Also double as Cool Masks.
Neil Peart of Rush has been wearing a traditional North African kufi since the early 1990's. It's primarily to keep sweat out of his eyes, and recent tours have seen him wearing customized ones with album artwork.
Kana for the sake of her costumes and... stuff.
Multi-instrumentalist Chris Funk of The Decemberists most often sports a trilby.
Mid- 1980's Elton John often wore straw boaters in concerts and music videos, to hide his receding hairline pre-hairweave operation. The late-80's saw him switch to caps.
Captain Beefheart with his top hat.
The music hall song "Where Did You Get That Hat?" is about this trope. The character in the song was left a hat so fabulous, everyone including the Prince of Wales asks him where he got it.
Marc Bolan, on the cover of the T. Rex album The Slider.
Pharrell Williams has an oversized hat that is pretty much a meme unto itself.
Patrick Stump of Fall Out Boy. Buzzfeed has a definitive timeline of the hats he's worn.
Fishbone front man Angelo Moore has his signature derby.