Challenging Caps

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1000+ items

Dumpster Fire Response Team Chaos Humor Problem Solver Baseball Cap

HumansStuck12

$25.19

~~$31.49~~ (20% off)

Small Is Challenging Cute Minimalist Japanese Quote Art Dad Hat

Schulz Lightprint Studio

$23.19

~~$27.29~~ (15% off)

Anime Biker Girl "Let's Race" Motorcycle Dad Hat

unboxedbyJuls

$19.62

~~$23.09~~ (15% off)

Dumpster Fire Response Team Chaos Manager Funny Work Gift Baseball Cap

JonesFlora2025

$25.19

~~$31.49~~ (20% off)

Hidden Truth – Ethereal Ghost & Pastel Hearts Aesthetic Baseball Cap

ANoelleART

$18.47

~~$23.09~~ (20% off)

TRIAL RIDE THE IMPOSSIBLE Extreme Acrobatic Motorcycle Motorsport Trial Riders and Fans Dad Hat

Jt41

$21.41

~~$25.19~~ (15% off)

Today’s challenges pave the way for your future Dad Hat

Mountain-Point

$19.62

~~$23.09~~ (15% off)

Multicolored Aggressive Geometric Chimpanzee Sticker – Low Poly Impact Art for Urban Style Baseball Cap

bsbd-action

$18.47

~~$23.09~~ (20% off)

It’s a process, not impossible Baseball Cap

GlimmerAura

$18.47

~~$23.09~~ (20% off)

Looking For A Bad Time (Challenging Phrase, Dark Humor, Gamer Style, Design) Baseball Cap

AstronautMerch

$19.64

~~$24.56~~ (20% off)

No Work No School No Shopping Workers Over Billionaires Labor Rights Quote Dad Hat

SkeletonsDanger

$24.98

~~$29.39~~ (15% off)

ALWAYS RELEVANT IN ITS IMPERTINENCE! Dad Hat

francoisville

$21.41

~~$25.19~~ (15% off)

CANAILLE PLUS! Baseball Cap

francoisville

$20.15

~~$25.19~~ (20% off)

Firebrand Definition Baseball Cap

OFF-ROAD TRUCKERS MUD BLOOD AND GEARS pickup trucks off-roaders big wheels challenging terrain Dad Hat

Jt41

$21.41

~~$25.19~~ (15% off)

TRIAL acrobatic motorcycle motorsport trial riders trial fans motorcycle enthusiasts Baseball Cap

Jt41

$20.15

~~$25.19~~ (20% off)

Trial Rider - Vintage Varsity Style Extreme Motorcycle Sports Typography Baseball Cap

Jt41

$20.15

~~$25.19~~ (20% off)

Sceptic Challenging Beliefs Through Thoughtful Expression Dad Hat

RF-73

$19.62

~~$23.09~~ (15% off)

The Greatest Views Require the Most Challenging Climbs – Summit Worth It Baseball Cap

Dxvect

$20.15

~~$25.19~~ (20% off)

Young Spartan Girls Challenging Boys by Edgar Degas: Classical Impressionist Poster Baseball Cap

artofuniverse

$21.83

~~$27.29~~ (20% off)

Worth Restarting Everything – Hardcore Gamer Valentine Shirt Dad Hat

KapiPrint

$22.30

~~$26.24~~ (15% off)

My Happy Place - Golf Course Dreams Baseball Cap

ArtelierMe

$20.99

~~$26.24~~ (20% off)

TRIAL motorcycle motorsport best riders trial rider trial races Dad Hat

Jt41

$21.41

~~$25.19~~ (15% off)

Item preview, HARD TRAILS TOUGH GUYS hard enduro riders trail adventures best riders in the world motorcycle motorsport designed and sold by Jt41.

HARD TRAILS TOUGH GUYS hard enduro riders trail adventures best riders in the world motorcycle motorsport Dad Hat

Jt41

$21.41

~~$25.19~~ (15% off)

Fire illustration consume Baseball Cap

godPapa

$20.15

~~$25.19~~ (20% off)

I am a bad influence (fo) Baseball Cap

XUSRedbubble

$20.15

~~$25.19~~ (20% off)

I'm a bad influence (fc) Dad Hat

XUSRedbubble

$21.41

~~$25.19~~ (15% off)

No Fear Live Bold Dad Hat

vivian011425

$19.62

~~$23.09~~ (15% off)

Buy the Dip They Said Dad Hat

venomousvector

$21.41

~~$25.19~~ (15% off)

Dark Fantasy Bonfire Knight T-Shirt | Rest and Try Again Souls-Inspired Tee Baseball Cap

GeniePixel

$20.15

~~$25.19~~ (20% off)

White Knight on Horse - High Detail Pop Surrealism Through the Looking Glass Art Print Dad Hat

Art's Diner

$19.62

~~$23.09~~ (15% off)

King of Hearts Royal Court - High Detail Pop Surrealism Alice in Wonderland Art Print Dad Hat

Art's Diner

$19.62

~~$23.09~~ (15% off)

Bill the Lizard on Ladder - High Detail Pop Surrealism Alice in Wonderland Art Print Baseball Cap

Art's Diner

$18.47

~~$23.09~~ (20% off)

Tweedledee and Tweedledum - High Detail Pop Surrealism Alice in Wonderland Art Print Dad Hat

Art's Diner

$19.62

~~$23.09~~ (15% off)

The Duchess and Pig-Baby - High Detail Pop Surrealism Alice in Wonderland Art Print Dad Hat

Art's Diner

$19.62

~~$23.09~~ (15% off)

Knave of Hearts & Alice - High Detail Pop Surrealism Wonderland Trial Art Print Dad Hat

Art's Diner

$19.62

~~$23.09~~ (15% off)

The Gryphon Alice in Wonderland Art Print - High Detail Pop Surrealism Mythology Painting Baseball Cap

Art's Diner

$18.47

~~$23.09~~ (20% off)

March Hare Mad Tea Party Art Print - Pop Surrealism Alice in Wonderland Painting Dad Hat

Art's Diner

$19.62

~~$23.09~~ (15% off)

Humpty Dumpty Alice in Wonderland Art Print - High Detail Pop Surrealism Illustration Baseball Cap

Art's Diner

$18.47

~~$23.09~~ (20% off)

Item preview, MY THERAPIST DIDN'T MAKE IT funny challenging patient stress and problems talking on the couch psychiatric designed and sold by Jt41.

MY THERAPIST DIDN'T MAKE IT funny challenging patient stress and problems talking on the couch psychiatric Baseball Cap

Jt41

$20.15

~~$25.19~~ (20% off)

EXPENSIVE & DIFFICULT Dad Hat

oddwonders

$21.41

~~$25.19~~ (15% off)

EXPENSIVE & DIFFICULT Dad Hat

oddwonders

$21.41

~~$25.19~~ (15% off)

EXPENSIVE & DIFFICULT Baseball Cap

oddwonders

$20.15

~~$25.19~~ (20% off)

EXPENSIVE & DIFFICULT Dad Hat

oddwonders

$21.41

~~$25.19~~ (15% off)

Item preview, SECTION OBSERVER Trial section observer race official marks zero mark trial rider trial motorcycle motorsports motorbike designed and sold by Jt41.

SECTION OBSERVER Trial section observer race official marks zero mark trial rider trial motorcycle motorsports motorbike Dad Hat

Jt41

$21.41

~~$25.19~~ (15% off)

These Are Difficult Times Dad Hat

FadeOfThrone

$21.41

~~$25.19~~ (15% off)

Motocross Rider Kicking Up Dust at Sunset Dad Hat

homydesign

$19.12

~~$22.49~~ (15% off)

arachne challenging athena Dad Hat

matintheworld ( delcarmat )

$19.62

~~$23.09~~ (15% off)

Dark Soulslike Player Aesthetic Baseball Cap

bapupa

$20.15

~~$25.19~~ (20% off)

Soulslike Player Dad Hat

bapupa

$21.41

~~$25.19~~ (15% off)

Dark Soulslike Player Gaming Dad Hat

bapupa

$21.41

~~$25.19~~ (15% off)

NO PAIN NO POWER T-Shirt - Red Wings Kettlebell Functional Fitness Tee Dad Hat

Design-Pro-21

$21.41

~~$25.19~~ (15% off)

Trippin' For A Livin' Funny Skeleton Electrician Lover Baseball Cap

Clairenity Studio

$18.47

~~$23.09~~ (20% off)

Trippin' For A Livin' Funny Skeleton Electrician Lover Dad Hat

Clairenity Studio

$19.62

~~$23.09~~ (15% off)

Trippin' For A Livin' Funny Skeleton Electrician Lover Baseball Cap

Clairenity Studio

$18.47

~~$23.09~~ (20% off)

Old Man Smiling with a Syringe Dad Hat

Naux | Design & Illustration

$29.44

~~$34.63~~ (15% off)

Item preview, HARD ENDURO TRAIL THERAPY Extreme Motorcycle Motorsport hard enduro rider best riders in the world to the challenging forest trails designed and sold by Jt41.

HARD ENDURO TRAIL THERAPY Extreme Motorcycle Motorsport hard enduro rider best riders in the world to the challenging forest trails Baseball Cap

Jt41

$20.15

~~$25.19~~ (20% off)

Local Trails, Legendary Pain Baseball Cap

AchromaticM

$20.15

~~$25.19~~ (20% off)

Vintage City Magazine - Luther "Golden Eyes" Marlowe - Gangster Baseball Cap

Vintage City

$20.15

~~$25.19~~ (20% off)

Puzzlers Sort It Out - Puzzles Game Puzzle Lover Hobbyist Dad Hat

RatCurry

$21.41

~~$25.19~~ (15% off)

Solving Puzzles Is My Superpower Puzzle Lover Jigsaw Puzzle Baseball Cap

MelSurf

$20.15

~~$25.19~~ (20% off)

Slaughterhouse Dad Hat

Naux | Design & Illustration

$29.44

~~$34.63~~ (15% off)

Trailblazer Motocross Helmet Dirt Bike Rider Gift Baseball Cap

RNASstuff

$19.81

~~$24.77~~ (20% off)

Soulslike Art: Widow of Thorns Dad Hat

bapupa

$21.41

~~$25.19~~ (15% off)

Soulslike Art: Veil of Rot Dad Hat

bapupa

$21.41

~~$25.19~~ (15% off)

Soulslike Art: The Hollow Seraph Baseball Cap

bapupa

$20.15

~~$25.19~~ (20% off)

Soulslike Art: The Forsaken Choir Dad Hat

bapupa

$21.41

~~$25.19~~ (15% off)

Soulslike Art: The Drowned King Baseball Cap

bapupa

$20.15

~~$25.19~~ (20% off)

Soulslike Art: The Bone Colossus Dad Hat

bapupa

$21.41

~~$25.19~~ (15% off)

Soulslike Art: Hollow Prayer Baseball Cap

bapupa

$20.15

~~$25.19~~ (20% off)

Soulslike Art: Harbinger of Ash Baseball Cap

bapupa

$20.15

~~$25.19~~ (20% off)

Soulslike Art: Grave of Kings Baseball Cap

bapupa

$20.15

~~$25.19~~ (20% off)

Soulslike Art: Eternal Echo Baseball Cap

bapupa

$20.15

~~$25.19~~ (20% off)

Soulslike Art: Cursed Flame Baseball Cap

bapupa

$20.15

~~$25.19~~ (20% off)

Soulslike Art: Ashen Path Dad Hat

bapupa

$21.41

~~$25.19~~ (15% off)

Neurophytes of the brave new world Baseball Cap

TintoTain

$20.15

~~$25.19~~ (20% off)

Challenge everything ! Dad Hat

TintoTain

$21.41

~~$25.19~~ (15% off)

Vintage Gangster Criminal Elegant Suit Bad News, Good Taste Baseball Cap

Vintage City

$20.15

~~$25.19~~ (20% off)

Vintage Hot Gangster Criminal Elegant Suit Too Smooth to be caught Dad Hat

Vintage City

$21.41

~~$25.19~~ (15% off)

Vintage Hot Gangster Good Manners, Bad Intentions I like to see you try Dad Hat

Vintage City

$21.41

~~$25.19~~ (15% off)

Vintage Pretty Retro Girl I like to see you try Baseball Cap

Vintage City

$20.15

~~$25.19~~ (20% off)

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Challenging Caps

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