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Tang

Truly Feared Pyro
  • 20px-Leaderboard_class_scout.png
    Scout: Troublemakers Tossle cap
  • 20px-Leaderboard_class_soldier.png
    Soldier: Stainless pot
  • 20px-Leaderboard_class_pyro.png
    Pyro: Old Guadalajara
  • 20px-Leaderboard_class_demoman.png
    Demoman: Conjurors Cowl
  • 20px-Leaderboard_class_heavy.png
    Heavy: Hound dog
  • 20px-Leaderboard_class_engineer.png
    Engineer: Safe 'n' Sound
  • 20px-Leaderboard_class_medic.png
    Medic: Vintage Tyrolean
  • 20px-Leaderboard_class_sniper.png
    Sniper: Fruit Shoot
  • 20px-Leaderboard_class_spy.png
    Spy:
    Charmer's Chapeau
 
Scout - Whoopee Cap
Soldier - Stout Shako
Pyro - Birdcage
Demo - Carouser's Capotain (if I had to choose one, but I'd rather wear the Treasure Hat)
Heavy - Hard Counter
Engie - Engineer's Cap
Medic - Team Captain (or Blighted Beak)
Sniper - Fruit Shoot
Spy - Counterfeit Billycock
All Class - Max's Severed Head
 
Scout: Tossle Cap
Soldier: B.M.O.C / Team Captain
Pyro: Nappers / Bubble Pipe
Demoman: Stuntman / Tavish
Heavy: Team Captain
Engineer: VRH
Medic: Team Captain
Sniper: Anger / Robin
Spy: Dashin'
All-Class: Bill's Hat
 
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All Class: Towering Pillar of Hats.
Soldier: Grenadiers Softcap, to complete the tank buster set.
 
my favorite's my current one,
85px-Painted_Summer_Hat_141414_Carefree_Summer_Nap.png

but otherwise it would be..
Scout -
75px-Item_icon_Baseball_Bill%27s_Sports_Shine.png

Soldier- .
85px-Painted_Sergeant%27s_Drill_Hat_E6E6E6.png

Pyro-
75px-Item_icon_Stately_Steel_Toe.png

Demo-
77px-Painted_Mask_of_the_Shaman_141414.png

Heavy-
75px-Item_icon_Dragonborn_Helmet.png

Engie-
84px-Painted_Safe%27n%27Sound_E6E6E6.png

Medic-
75px-Item_icon_Grimm_Hatte.png

Sniper-
43px-Painted_Fruit_Shoot_E6E6E6_Tasty.png

Spy-
85px-Painted_Backbiter%27s_Billycock_2D2D24.png

All Class-
75px-Item_icon_Holiday_Headcase.png
 
Scout: Ye Olde Baker Boy
Soldier: Honcho's Headgear
Pyro: Flamboyant Flamenco
Demo: Hussler's Hallmark
Engy: Texas Ten-Gallon
Heavy: Hound Dog
Medic: Prussian Pickelhaube or Vintage Tyrolean
Sniper: Desert Marauder
Spy: Cosa Nostra or Fancy Fedora
 
Scout: Hero's Tail
Soldier: Defiant Spartan
Pryo: Head Warmer
Demoman: Prince Tavish Crown
Heavy: Dragonborn Helmet
Engineer: Safe n' Sound
Medic: Vintage Tyrolean
Sniper: Stovepipe Sniper Shako
Spy: Lacking Moral Fiber Mask
Allclass: 2010 Spine Chilling Skull or Max's Severed Head
 
Scout: Trouble Makers Tossle Cap
Soldier: Exquisite Rack
Pyro: The Attendent
Demoman: Tavish Degroot
Heavy: Tough Guys Toque
Engineer: Safe n Sound
Medic: Team Captain
Sniper: Anger
Spy: Fancy Fedora
 
Scout - Hero's Tail
Soldier - Killer's Kabuto
Pyro - Warith Wrap
Demo - Samur-Eye
Heavy - Genuine Pilokta
Engie - Safe n' Sound
Medic - Medi Mask
Sniper - Anger
Spy - Noh Mercy
Multiple- Bonedoiler
 
85px-Painted_Whoopee_Cap_729E42.png
85px-Painted_Superfan_141414.png
65px-Painted_El_Jefe_2D2D24.png
90px-Backpack_Baseball_Bill%27s_Sports_Shine.png
77px-Painted_Napper%27s_Respite_18233D.png
74px-BLU_Point_and_Shoot.png
95px-BLU_Humanitarian%27s_Hachimaki.png


And from da miscs:
90px-Backpack_Sight_for_Sore_Eyes.png
85px-Painted_Teufort_Tooth_Kicker_B8383B.png
95px-RED_Triad_Trinket.png
85px-Painted_Summer_Shades_B8383B.png
90px-Backpack_Something_Special_For_Someone_Special.png
... and pretty much all Scout miscs in black or green.
 
90px-Backpack_Ye_Olde_Baker_Boy.png
90px-Backpack_Bombing_Run.png
90px-Backpack_Chieftain%27s_Challenge.png
90px-Backpack_Honcho%27s_Headgear.png
90px-Backpack_Stahlhelm.png
90px-Backpack_Respectless_Rubber_Glove.png
90px-Backpack_Vintage_Merryweather.png
90px-Backpack_Attendant.png
90px-Backpack_Flamboyant_Flamenco.png
90px-Backpack_Sober_Stuntman.png
90px-Backpack_Scotch_Bonnet.png
90px-Backpack_Tavish_DeGroot_Experience.png
90px-Backpack_Officer%27s_Ushanka.png
90px-Backpack_Magnificent_Mongolian.png
90px-Backpack_Pilotka.png
90px-Backpack_Western_Wear.png
90px-Backpack_Ol%27_Geezer.png
90px-Backpack_Buzz_Killer.png
90px-Backpack_Surgeon%27s_Stahlhelm.png
90px-Backpack_Gentleman%27s_Ushanka.png
90px-Backpack_Combat_Medic%27s_Crusher_Cap.png
90px-Backpack_Master%27s_Yellow_Belt.png
90px-Backpack_Shooter%27s_Sola_Topi.png
90px-Backpack_Magistrate%27s_Mullet.png
90px-Backpack_Familiar_Fez.png
90px-Backpack_L%27Inspecteur.png
90px-Backpack_Voodoo_Juju.png
90px-Backpack_Private_Eye.png
90px-Backpack_Team_Captain.png
 
Scout- Front Runner
Soldier- Tyrant's Helm
Pyro- Pyromancer's Mask
Demoman- Prince Tavish's Crown
Heavy- Outdoorsman
Engineer- Texas Ten-Gallon
Medic- N/A
Sniper- Larrikan Robin
Spy- L'Inspecteur
 
I'm gonnna just say by what I play mostly:

Solly: Hat with no name
Sniper: Crocoleather slouch
All classes: Bills hat/company man tie
Demo: Bearded bombardier
 
TS All-Father and Lord Cockswain's Pith Helmet is a good combo.
I actually like most of the soldier hats. I wish there was a way to have a cycle of hats, instead of having to manually switch it.
 
When I was a F2P nub:
Scout: Ghastly Gibus
Soldier: Ghastly Gibus
Pyro: Ghastly Gibus
Demoman:Ghastly Gibus
Heavy: Ghastly Gibus
Engineer: Ghastly Gibus
Medic: Ghastly Gibus
Sniper: Ghastly Gibus
Spy: Ghastly Gibus
All Class: Ghastly Gibus

Nowadays:
Scout: The Hermes
Soldier: Cross-Com Crash Helmet
Pyro: Vintage Merryweather+Hazmat Headcase
Demoman: Tavish de Groot Experience
Heavy: Team Captain
Engineer: Company Man
Medic: Grimm Hatte + Blighted Beak
Sniper: Company Man
Spy: L'Inspecteur
All Class: Mann Co. Cap
 
Scout- Backwards Ballcap
Soldier- Stainless Pot
Pyro- Nappers Respite or TS Respectless Rubber Glove
Demoman- Reggaelator
Heavy- One Man Army
Medic- Surgeon's Stahlhelm
Engineer- Industrial Festiviser
Sniper- Bloke's Bucket Hat
Spy- Cosa Nostra Cap

My favorite all class would probably be a TS Bills