Bobby Singer is a man who wears many hats—literally. Whether inside at home doing research, or out on a case kicking some monster's ass—or saving Sam and Dean's—Bobby almost always appears wearing one of his trucker's caps.
For such a hat lover, it may be surprising that Bobby only appears to have owned 8 different hats. Most of them appear in well-worn condition, although the hat he wears most often—The Blue and White Hat—remains cleaner than most.
When Garth becomes "the new Bobby"—taking on Bobby's role helping other hunters—he wears Bobby's Green and White Hat (which Bobby last wore in 6.04 Weekend at Bobby's), which he says Bobby left in his car when they were on a hunt together. Dean is annoyed, and takes it from him, saying he is not wearing it correctly. Once Dean accepts Garth's new role, he shows Garth how to wear it.
The Green and White Hat
Description: White front with green sides and bill. Bobby's longest surviving hat. At some point it falls into Garth's possession and he now wears it as "the new Bobby."
The Eagle Hat
Description: Brown sides and bill. The white front has the word "Eagle" under a stylized wing design. There may be a faded eagle in the center.
The Blue and White Hat
Description: Dark blue front and bill with white sides. Bobby's favourite hat.
The Blue and White Hat, Mark II
Description: Blue front and bill with white sides, it is distinguished from the original blue and white hat by the double seam down the center.
The Winged Skull Hat
Description: White sides with a blue front and bill. The text on the front says "Death Valley Rebel," and there is a small outline of a human skull flanked by wings.
The Brown Hat
Description: All over brown hat with a light brown design on the front. Possibly with a very faded place name written on it.
The Magnificent Pig Hat
Description: A fancy hat in brown tones with a triple line of white stitching on the bill and an embroidered patch of a pig (pink on a green background) on the front.
The Blue Hat of Doom
Description: A blue hat with three small, parallel scratch marks on the top of the bill and slight fraying on the front edge of bill. Notably worn when he's shot and as a ghost. Worn when put to rest and his soul wears it in Hell and through his rescue by Sam and ascension into Heaven.
There have only been nine occasions when Bobby has appeared sans hat, and the first of these was not until Season 3. Fans were delighted to finally see the top of Bobby's head!
Bobby generally wears one cap per episode, but there have been a few in which he wears several different ones:
• 3.01 The Magnificent Seven Caps: 1 & hatless.
• 3.04 Sin City Caps: 2.
• 3.10 Dream a Little Dream of Me Caps: 2 & hatless.
• 5.01 Sympathy for the Devil Caps: 1 & hatless.
• 5.15 Dead Men Don't Wear Plaid Caps: 1 & hatless.
• 6.04 Weekend at Bobby's Caps: 2.
• 6.16 ...And Then There Were None Caps: 1 & hatless.
• 6.21 Let It Bleed Caps: 1 & hatless.
• 7.01 Meet the New Boss Caps: 2.
• 7.03 The Girl Next Door Caps: 2 & hatless.
• 7.06 Slash Fiction Caps: 2
• 7.09 How to Win Friends and Influence Monsters Caps: 1 & hatless.
• 7.10 Death's Door Caps: 1 & hatless