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Old School Life Caps
1000+ items
Hats
Filters (2)
1000+ items
Newest
Vintage High School Tribute Design with Classic Retro Style Baseball Cap
Jenil225
$26.19
$32.74
(20% off)
Life Death Duality Tattoo Art Baseball Cap
MCKENZIENAVR
$20.15
$25.19
(20% off)
Rock Band Dad Hat
Tee Trendy
$21.41
$25.19
(15% off)
Oliver Tree ALIEN BOY Dad Hat
DebutCatgirl
$35.68
$41.98
(15% off)
Oliver Tree ALIEN BOY Dad Hat
DebutCatgirl
$35.68
$41.98
(15% off)
Oliver Tree China Dad Hat
DebutCatgirl
$35.68
$41.98
(15% off)
Oliver Tree Don't Cry Dad Hat
DebutCatgirl
$35.68
$41.98
(15% off)
Oliver Tree fan art Dad Hat
DebutCatgirl
$35.68
$41.98
(15% off)
Oliver Tree Cowboys Don't Cry Baseball Cap
DebutCatgirl
$33.58
$41.98
(20% off)
Rock Band Dad Hat
JaThomae
$21.41
$25.19
(15% off)
Gen X The Badass Generation Before All You Sissies Were Born Generation X Pride Dad Hat
RetroMini2026
$26.76
$31.49
(15% off)
Vintage Hockey Team Est 1974 Baseball Cap
ZiqiPyatt
$22.67
$28.34
(20% off)
Neighborhood Corner Store Illustration Dad Hat
Angelic Gangster
$19.62
$23.09
(15% off)
Analog Nostalgia Retro Technology Graphic Dad Hat
ChicTrendz
$21.41
$25.19
(15% off)
Retro Music Vibes - Vintage Vinyl, Cassette Tape & Boombox Grid Baseball Cap
MyHappyArtShop
$17.80
$22.25
(20% off)
Never Forget Retro Floppy Disk VHS Cassette Funny Gift Baseball Cap
ScienceCorner
$20.15
$25.19
(20% off)
Never Forget Retro Floppy Disk VHS Cassette Funny Gift Dad Hat
ScienceCorner
$21.41
$25.19
(15% off)
Classic American Diesel Trucker Retro Big Rig Vibe | Best Buy Baseball Cap
JeremyMcs
$27.87
$34.84
(20% off)
My Record Collection Has Better Stories Vintage Vinyl Quote Shirt Dad Hat
Golden Era Studio
$19.62
$23.09
(15% off)
Vintage Underwood Manual Typewriter Aesthetic Retro Classic Writing Machine Illustration For Authors And Journalists | ⭐⭐⭐⭐⭐ Dad Hat
Wedoart-shop
$29.62
$34.84
(15% off)
Brotherhood Of The Highway Hey There Good Buddy Semi Truck Sunset Art Baseball Cap
NomadForge
$18.47
$23.09
(20% off)
Retro 80s Skateboarder Silhouette with Boombox and Urban City Sunset Dad Hat
V8Green
$21.82
$25.67
(15% off)
Wooden Recorder Music Notes Dad Hat
dRaBaBdesign
$21.41
$25.19
(15% off)
I Want My MTV Baseball Cap
310BrandLA
$20.15
$25.19
(20% off)
What's Your 20? Middle of Nowhere - Trucker GPS Map Art Baseball Cap
NomadForge
$18.47
$23.09
(20% off)
Livin' Low Life Lowrider, Kustom, Hot Rod, Muscle Car Baseball Cap
Elegant Customs
$18.47
$23.09
(20% off)
Tattooed Low Life Lowrider, Kustom, Hot Rod, Muscle Car Dad Hat
Elegant Customs
$19.62
$23.09
(15% off)
Grown Boy Built to Play Forced to Work – Retro Gamer Humor Baseball Cap
KalicoDesignUS
$18.47
$23.09
(20% off)
I'm Not Old, I'm A Classic - Funny Birthday Sarcasm Shirt Baseball Cap
Merchifyme2000
$18.47
$23.09
(20% off)
Driver's Daily Log - Living The Dream Trucker Logbook Art Baseball Cap
NomadForge
$18.47
$23.09
(20% off)
Retro High Performance Bmx Bicycle Motocross Classic Old School Style | Limited Edition Dad Hat
Niko234RT
$25.87
$30.44
(15% off)
Cool Vintage Dad Retro Vintage Design Dad Hat
Nacho Average Designs
$23.19
$27.29
(15% off)
DEAR INTERNET, I PREFER PAPER Dad Hat
WesWay
$18.73
$22.04
(15% off)
DEAR INTERNET, I PREFER PAPER Baseball Cap
WesWay
$17.63
$22.04
(20% off)
DEAR INTERNET, I PREFER PAPER Dad Hat
WesWay
$18.73
$22.04
(15% off)
DEAR INTERNET, I PREFER PAPER Dad Hat
WesWay
$18.73
$22.04
(15% off)
Vintage Southern Moonshiner Bootlegger Outlaw Country Legend | Best Buy Dad Hat
EinMM
$25.87
$30.44
(15% off)
Funny Retirement Racing Team Vintage Tractor Race Retro Comic Baseball Cap
frestshop
$18.47
$23.09
(20% off)
Angler's Legacy Tackle - Since 1927 Dad Hat
Merchifyme2000
$19.62
$23.09
(15% off)
Rust Bucket Auto Shop - We Fix Everything Est. 1950 Dad Hat
Merchifyme2000
$19.62
$23.09
(15% off)
Press Play on Life Vintage Cassette Retro Music Design Baseball Cap
zzedine
$18.47
$23.09
(20% off)
Classis R&B Baseball Cap
DeSeanSuperstarApparel
$21.83
$27.29
(20% off)
Spice Girls Baseball Cap
houdalego
$20.15
$25.19
(20% off)
Retro BMX Racing Champion Vintage Old School 80S Bicycle Art | Perfect Gift For You And Friends Dad Hat
ArizonaDream
$25.87
$30.44
(15% off)
Nobody Hits Harder Than Life – Traditional Boxer Tattoo Design Dad Hat
Scandi-Design
$21.41
$25.19
(15% off)
Make Rust not War! Rusty Rats Design Dad Hat
WonkyRebel
$19.62
$23.09
(15% off)
I’d Rather be Playing with my Rusty Junk! Baseball Cap
WonkyRebel
$18.47
$23.09
(20% off)
Rust is my Glitter! Rusty Rats Design Baseball Cap
WonkyRebel
$18.47
$23.09
(20% off)
Shiny is Overrated! Rusty Rats Design Baseball Cap
WonkyRebel
$18.47
$23.09
(20% off)
It’s Practically Brand New! Rusty Rats Design Baseball Cap
WonkyRebel
$18.47
$23.09
(20% off)
Retro Massey Ferguson Tractor Vintage Farm Equipment Classic Tractor Lover Gift | Limited Edition Baseball Cap
RzEditz
$20.15
$25.19
(20% off)
Please Be Patient With Me I'm From The 1900's Vintage Camper Van Life Generation Humor Baseball Cap
RetroMini2026
$25.19
$31.49
(20% off)
School My Old Enemy Dad Hat
MySimpleFlow
$21.41
$25.19
(15% off)
Old School Cabover – American trucker legend Dad Hat
Zerberus71
$21.41
$25.19
(15% off)
I Speak Fluent Five Year Old Baseball Cap
theartfulaspie
$20.15
$25.19
(20% off)
Life Sounds Better With Music Vintage Boombox Dad Hat
Mita986
$19.62
$23.09
(15% off)
BORN TO BITE Baseball Cap
gomood
$20.15
$25.19
(20% off)
Street Legacy Urban Boombox Graffiti Dad Hat
FABIOLA1970
$19.62
$23.09
(15% off)
Dark Academia Still Life — Vintage Scholar Aesthetic Art Print for Students Baseball Cap
Fanverse Merchandise
$20.15
$25.19
(20% off)
Skate Fast, Nap Hard Baseball Cap
SugarCore
$19.31
$24.14
(20% off)
AFK in Real Life – Retro Pixel Gaming Baseball Cap
BYVOK
$18.47
$23.09
(20% off)
Old School Fishing Tradition Vintage Angler Design Dad Hat
TeeVerse27
$21.41
$25.19
(15% off)
Fluent in Analog Gen X Retro 80s 90s Nostalgia Dad Hat
Gbriel3
$21.41
$25.19
(15% off)
Iron Therapy Training Graphic Weightlifting Gym Motivation Fitness Enthusiast Gift Barbell Workout Design Dad Hat
ByPawel
$21.41
$25.19
(15% off)
Just One More Level – Retro Gamer Vintage Gaming Design Dad Hat
Musamem Designs
$20.52
$24.14
(15% off)
Vital Life Giving Deity Sun Baseball Cap
scicilysimonee
$20.15
$25.19
(20% off)
NRH Fresh Donuts Retro Pin-Up Diner Poster Baseball Cap
Normandy Road Heritage™ - Vintage Garage Art
$20.15
$25.19
(20% off)
LIFE IS GOOD WITH CLASSIC Dad Hat
yourcar-auto
$19.62
$23.09
(15% off)
Vintage Orca Whale Art Print Retro Killer Whale Ocean Waves Pacific Northwest Nautical Baseball Cap
raedattia
$20.15
$25.19
(20% off)
Retro Analog Life Baseball Cap
Pecata
$18.47
$23.09
(20% off)
I'm Not Old, I'm Analog – Retro Cassette Edition Baseball Cap
Pecata
$18.47
$23.09
(20% off)
Bring Back the 80s Retro Computer Typography Dad Hat
TheWanderlight
$19.62
$23.09
(15% off)
Rock Never Gets Old T-Shirt | Vintage Rock and Roll Skull Music Tee Baseball Cap
Danny's Tees
$20.15
$25.19
(20% off)
Arcade Legend Gift - Retro Gaming Baseball Cap
RedRubyBubble
$20.15
$25.19
(20% off)
Arcade Legend Gift - Retro Gaming Baseball Cap
RedRubyBubble
$20.15
$25.19
(20% off)
Insert Coin Gift - Arcade Gamer Baseball Cap
RedRubyBubble
$20.15
$25.19
(20% off)
DJ Life Is So Cool Retro Vinyl Turntable Baseball Cap
Edwere
$18.47
$23.09
(20% off)
Arcade Dreams – Insert Coin to Continue Life Dad Hat
Selfique Bloom
$19.62
$23.09
(15% off)
Heritage Harvest Farms - Rooted in Tradition Est. 1905 Baseball Cap
Merchifyme2000
$18.47
$23.09
(20% off)
Life Has No Rewind Cassette Tape Poster - Enjoy Every Moment Motivational Wall Art Print Baseball Cap
scrambledpeg
$21.83
$27.29
(20% off)
Life Has No Rewind Vintage Cassette Tape Poster - Red Black Retro Motivational Wall Art Baseball Cap
scrambledpeg
$21.83
$27.29
(20% off)
Life Has No Rewind Cassette Tape Poster - Vintage Red Black Motivational Wall Art Print Baseball Cap
HappyGrandmaUB
$20.15
$25.19
(20% off)
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