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Old School Life Caps
1000+ items
Hats
Filters (2)
1000+ items
Newest
Mercury '51 Custom Vintage Kustom Baseball Cap
Normandy Road Heritage
$18.47
$23.09
(20% off)
Education Is Important But Video Games Are Importanter Funny Gamer Quote Baseball Cap
SkeletonsDanger
$25.19
$31.49
(20% off)
Vintage Classic Racing Car Colorful Baseball Cap
ea-photos
$21.83
$27.29
(20% off)
Retro Boombox Music T-shirt Dad Hat
FreakNRetro
$19.62
$23.09
(15% off)
Gen X Lots Of Memories No Evidence GenXer 80s 90s Nostalgia Cassette Retro Baseball Cap
SkeletonsDanger
$25.19
$31.49
(20% off)
Truckers Union Classic Pickup Baseball Cap
Retro Arabica
$18.47
$23.09
(20% off)
King of Life Graffiti Crown Streetwear Baseball Cap
Ekstrashop
$18.47
$23.09
(20% off)
Surf Life Club Retro Checkerboard Beach Aesthetic Graphic Dad Hat
AdyKurniawan
$21.41
$25.19
(15% off)
Start a band Baseball Cap
Lenock
$18.47
$23.09
(20% off)
The vibes of the 80’s Dad Hat
LsartShop
$19.62
$23.09
(15% off)
Slow & Low Baseball Cap
checkoutmyengine
$20.15
$25.19
(20% off)
The Legend Has Retired Vintage Retirement Celebration Typography Design Dad Hat
msaloyach
$19.62
$23.09
(15% off)
Saltwater Soul Vintage Nautical Anchor Compass Dad Hat
weeomano
$21.41
$25.19
(15% off)
80s Child Analog Large Cassette Nostalgia Saying Baseball Cap
pirminio
$20.99
$26.24
(20% off)
I Survived the Analog Era | Nostalgic Humor & Retro Vibes Dad Hat
EverClassic
$21.40
$25.18
(15% off)
Please Be Patient With Me I'm From 1900s, Funny Meme, Funny 90s, Funny Gift For Friend Baseball Cap
Sprinkle12345
$20.15
$25.19
(20% off)
Vintage Farm Tractor Cottagecore Agriculture Baseball Cap
SplashTastic
$17.63
$22.04
(20% off)
Aint Got No Gas In It Funny Vintage Lawn Mower Graphic Art Dad Hat
DaphoLatara
$21.41
$25.19
(15% off)
Theres No Life Like The Low - Lowrider, Kustom, Hot Rod, Muscle Car Dad Hat
Elegant Customs
$19.62
$23.09
(15% off)
Life Happens GettingTattoos Helps Baseball Cap
BrokenApparel
$20.99
$26.24
(20% off)
Retro Nostalgia Attitude Aesthetic Minimalist Graphic Dad Hat
Saniyamirza07
$19.62
$23.09
(15% off)
Heritage Farm Tractor Vintage Agriculture Badge Dad Hat
SplashTastic
$18.73
$22.04
(15% off)
Exam Days Felt Bigger Than Life Baseball Cap
pradeepvisuals
$20.15
$25.19
(20% off)
The Small Victories Meant The Most Dad Hat
pradeepvisuals
$21.41
$25.19
(15% off)
Agricultural Machinery Est 1952 Vintage Farming Rustic Tractor Baseball Cap
SplashTastic
$17.63
$22.04
(20% off)
Airborne '86 BMX T-Shirt Old School Freestyle BMX Retro Baseball Cap
Tee-Shirt-Topia
$20.99
$26.24
(20% off)
B-Boy Street Style Baseball Cap
G-shirts40
$28.54
$35.68
(20% off)
Screens Small, Memories Huge Y2K Poster Dad Hat
Sketchlegacy
$24.98
$29.39
(15% off)
Funny Running Humor Retro Sports Athletic Saying Design Baseball Cap
Zayavca
$20.99
$26.24
(20% off)
I Don't Snip I Clip - Funny Barber Clipper Vintage Barbershop Baseball Cap
SidTastic
$19.98
$24.98
(20% off)
American Traditional Seashell Floral Dad Hat
tradstix
$19.62
$23.09
(15% off)
Can I Kick It? Yes You Can! Old School Hip Hop Cartoon Dad Hat
JMS-Artvintage
$19.98
$23.51
(15% off)
Holographic VHS Tape Retro 90s Nostalgia Quote For Millennials Baseball Cap
roarsomethings
$18.81
$23.51
(20% off)
Red Muscle Car Retro Sunset Design | Classic Car Lover Gift | Built In The Past Driven By Soul Baseball Cap
Akseries
$17.63
$22.04
(20% off)
Saving Lives Since Before It Was Cool Retro Nurse Shirt Vintage Nursing Gift Dad Hat
Urbancraftup
$22.30
$26.24
(15% off)
Analogue Music Baseball Cap
LadyCaffiene
$18.47
$23.09
(20% off)
Vintage Racing Club Retro Motorsport Car Design Baseball Cap
Ivory Code
$18.47
$23.09
(20% off)
Vintage Chopper Motorcycle Baseball Cap
ubeyeart
$20.15
$25.19
(20% off)
School Trips Started Before The Classroom Dad Hat
pradeepvisuals
$21.41
$25.19
(15% off)
Too Old To Fight Still Ride Biker Skull Vintage Motorcycle Enthusiast Dad Hat
haitrieuic96
$21.41
$25.19
(15% off)
Please Be Patient With Me I'm From The 1900s Generational Humor Baseball Cap
HumansStuck12
$25.19
$31.49
(20% off)
Retro Coastal Cruiser Classic Sedan Baseball Cap
JBX Design
$18.47
$23.09
(20% off)
Gen X Raised On Hose Water & Neglect Generation X Humor Baseball Cap
RetroMini2026
$25.19
$31.49
(20% off)
Vintage 1978 Surf Magazine Cover Aesthetic Dad Hat
redblink store
$21.41
$25.19
(15% off)
Gen X Raised On Hose Water & Neglect Generation X Humor Baseball Cap
HumansStuck12
$25.19
$31.49
(20% off)
Snap Life Vintage Retro SLR Camera Dad Hat
GiggleInkTees
$21.41
$25.19
(15% off)
Vintage Gramophone Minimalist Line Art Dad Hat
redblink store
$21.41
$25.19
(15% off)
Powered by Dad Jokes and Bad Knees Running Baseball Cap
RunningWhiskers
$18.47
$23.09
(20% off)
Deebo's Bicycle Repo Vintage Cycle Stamp Dad Hat
Random-Toon
$21.41
$25.19
(15% off)
I Am Older Than The Internet Baseball Cap
Frank Ring
$20.15
$25.19
(20% off)
I Am Older Than The Internet Baseball Cap
Frank Ring
$20.15
$25.19
(20% off)
Vintage Tattoo Studio Bulldog with Rebellious Ink Culture Baseball Cap
Modaozushi216
$19.98
$24.98
(20% off)
Cozy Anteater Listening to Radio Retro Aesthetic Dad Hat
Cozy Vintage Animal
$23.19
$27.29
(15% off)
Generation X Before The Internet Ruled The World Nostalgia Culture Dad Hat
RetroMini2026
$26.76
$31.49
(15% off)
Back When Life Was Simple Retro Nostalgia Design Dad Hat
Smoking_Animals
$21.41
$25.19
(15% off)
Level Up Your Life – Retro 16-Bit Adventure Baseball Cap
Shaw1Berry
$18.47
$23.09
(20% off)
Will date any old thing archaeologist Baseball Cap
Peerless-Prime
$50.37
$62.97
(20% off)
The Classroom Was Our Whole Universe Dad Hat
pradeepvisuals
$21.41
$25.19
(15% off)
When Learning Felt Personal And Real Baseball Cap
pradeepvisuals
$20.15
$25.19
(20% off)
School Memories That Never Really Left Baseball Cap
pradeepvisuals
$20.15
$25.19
(20% off)
Tattooed Bulldog Artist Vintage Tattoo Culture Humor Illustration Baseball Cap
eliramaison
$19.98
$24.98
(20% off)
Vintage Tattoo Bulldog Poster with Old School Ink Shop Energy Baseball Cap
Modaozushi216
$19.98
$24.98
(20% off)
2Pac Thug Life Retro Hip Hop Cassette Poster Rap Wall Art Dad Hat
Tabloblog
$19.62
$23.09
(15% off)
Vintage Barber Skull with Classic Old School Shop Style Dad Hat
Modaozushi216
$21.23
$24.98
(15% off)
Legendary Bulldog Barber Vintage Shop with Classic Tattoo Vibes Baseball Cap
Modaozushi216
$19.98
$24.98
(20% off)
Cool Bulldog Barber Boss Vintage Tattoo Shop Poster Dad Hat
Modaozushi216
$21.23
$24.98
(15% off)
French Bulldog Barber Vintage Poster with Old School Shop Energy Dad Hat
Modaozushi216
$21.23
$24.98
(15% off)
Vintage Lion Barber Poster with Bold Grooming Shop Atmosphere Dad Hat
Modaozushi216
$21.23
$24.98
(15% off)
Vintage Skull Barber with Classic Barbershop Old School Vibes Baseball Cap
Modaozushi216
$19.98
$24.98
(20% off)
20 Cigarettes Vintage Smoker Graphic Retro Tobacco Art Dad Hat
Mind-Drift
$19.62
$23.09
(15% off)
Vintage Barber Illustration with Classic Grooming Shop Style Dad Hat
Modaozushi216
$21.23
$24.98
(15% off)
Vintage Barber Bulldog Illustration with Classic Barbershop Style Dad Hat
Modaozushi216
$21.23
$24.98
(15% off)
Vintage Bulldog Barber Shop with Old School Grooming Vibe Baseball Cap
Modaozushi216
$19.98
$24.98
(20% off)
Vintage Bulldog Barber Shop With Classic Grooming Attitude Baseball Cap
Modaozushi216
$19.98
$24.98
(20% off)
Vintage Bulldog Barber with Classic Barbershop Lifestyle Vibes Baseball Cap
Modaozushi216
$19.98
$24.98
(20% off)
Thug Life - west coast old school rap culture Baseball Cap
Hussar08
$20.15
$25.19
(20% off)
Thug Life - West Coast Old School Rap Culture Baseball Cap
Hussar08
$20.15
$25.19
(20% off)
Vintage Red Tractor - Field Tested Retro Farming Dad Hat
Smoking_Animals
$21.41
$25.19
(15% off)
Level 50 Unlocked Retro Gamer Birthday Celebration Since 1976 Baseball Cap
FGTV2021
$20.99
$26.24
(20% off)
Classic V8 Power - Retro 80s American Car Aesthetic Dad Hat
Zenvaro
$19.62
$23.09
(15% off)
Curling Dad Retro Sports Lettering Vintage Ice Game Style Baseball Cap
zamiokaline
$19.98
$24.98
(20% off)
Born On The Pond True Hockey Roots Vintage Illustration Dad Hat
AMSPHY
$19.62
$23.09
(15% off)
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