Threadless
Sell
Your Art
Retro orange striped strip banner promoting graphic t-shirts on sale

Headwear insecure Hats

Show: Products/Designs
Sort by: Relevance/Trending/Popular/New

Shop Headwear insecure Hats at Threadless. Every hat here started out as art by an independent artist — printed on demand and ready to ship.

  1. Cat Lover
    Cat Lover by tobefonseca
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  2. The Vinyl System
    The Vinyl System by Gamma-Ray
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  3. Worry Later
    Worry Later by TeoZ
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  4. Worship Coffee
    Worship Coffee by stevenrhodes
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  5. Cat Tree
    Cat Tree by tobefonseca
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  6. Earth with Moon balloon
    Earth with Moon balloon by wawawiwa
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  7. Retro Hoth
    Retro Hoth by rocketmantees
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  8. Felix the cat vintage
    Felix the cat vintage by rocketmantees
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  9. Meteor Thrower
    Meteor Thrower by digitalcarbine
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  10. Black Hole Glitch
    Black Hole Glitch by digitalcarbine
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  11. Eat The Rich
    Eat The Rich by rocketmantees
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  12. Ah The Element of Surprise Project Hail Mary
    Ah The Element of Surprise Project Hail Mary by rocketmantees
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  13. Royal
    Royal by milkbarista
    $29.95
  14. Ghost Of Disapproval
    Ghost Of Disapproval by obinsun
    $38.45
  15. I Love Being Around You
    I Love Being Around You by nathanwpyle1982
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  16. think twice?
    think twice? by poorlycatdraw
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  17. Tokyo Zoo
    Tokyo Zoo by DinoMike
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  18. Crescent Moon Glitch
    Crescent Moon Glitch by digitalcarbine
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  19. Captain Obvious!
    Captain Obvious! by polynothing
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  20. Project Amaze
    Project Amaze by rocketmantees
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  21. Guerni-Cats
    Guerni-Cats by vincenttrinidad
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  22. Ghost Busted
    Ghost Busted by Naolito
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  23. The Future is Analogue
    The Future is Analogue by rocketmantees
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  24. Kiwi Anatomy
    Kiwi Anatomy by McDanger
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  25. Funkalicious
    Funkalicious by Fen
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  26. Prehistoric Monster Japan Mount Fuji
    Prehistoric Monster Japan Mount Fuji by rocketmantees
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  27. AT AT Walker Assault Squad
    AT AT Walker Assault Squad by rocketmantees
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  28. Space Hop
    Space Hop by digitalcarbine
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  29. Runnin' Rhino
    Runnin' Rhino by alanis
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  30. USCSS Nostromo Weyland Yutani Logo Alien Spaceship
    USCSS Nostromo Weyland Yutani Logo Alien Spaceship by rocketmantees
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  31. Know Your Dinosaurs
    Know Your Dinosaurs by limetree
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  32. Not a Pipe
    Not a Pipe by alexmdc
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  33. Mister Mittens' Big Adventure
    Mister Mittens' Big Adventure by speedyjvw
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  34. Haikus Are Easy, But Sometimes...
    Haikus Are Easy, But Sometimes... by DesignbyProxy
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  35. Not Fast, Not Furious
    Not Fast, Not Furious by DinoMike
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  36. Schrodinger's Venn Diagram
    Schrodinger's Venn Diagram by Nathan Joyce
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  37. Freddie Mercury
    Freddie Mercury by Wirdou
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  38. Octopus Bike
    Octopus Bike by alanmaia
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  39. Lions Are Smarter Than I Am
    Lions Are Smarter Than I Am by keithmore
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  40. The Communist Party
    The Communist Party by tomburns
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  41. Bird of Fire
    Bird of Fire by ThePaperCrane
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  42. Infinity MPG
    Infinity MPG by arzie13
    $29.95
  43. Afternoon Delight
    Afternoon Delight by chrisbishop
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  44. The Collector
    The Collector by camillechew
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  45. Well, This Just Really Sucks...
    Well, This Just Really Sucks... by kreamy
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  46. The Great Retro Wave
    The Great Retro Wave by vincenttrinidad
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  47. Planet System
    Planet System by b3rni
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
  48. The Magician
    The Magician by xizann
    $27.45Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time. $22
* Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time.