Challenging Sweatshirts & Hoodies

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1000+ items

sisu Premium Oversized Sweatshirt

chuckleharski

$62.00

that's a challenging wank meme - im up to the challenge tho (black) Premium Oversized Sweatshirt

MillennialMemer

$69.75

that's a challenging wank meme - im up to the challenge tho Premium Oversized Hoodie

MillennialMemer

$77.63

Dark Fantasy Bonfire Knight T-Shirt | Rest and Try Again Souls-Inspired Tee Premium Oversized Sweatshirt

GeniePixel

$62.00

Challenging motivational quote Premium Oversized Sweatshirt

Duaxstudios11

$62.00

PIECE OF SHIT FUCKING APP Lightweight Sweatshirt

Doogermann

$46.19

If it was easy anybody could do it. Premium Oversized Sweatshirt

Qzmet

$56.84

Young and challenging Premium Oversized Hoodie

akrmsydra123

$69.00

Challenging Lightweight Hoodie

NBento

$36.74

challenging Pullover Sweatshirt

ninov94

$41.94

challenging Premium Oversized Sweatshirt

artaniparis

$62.00

I'm not Challenging Premium Oversized Hoodie

ZenPhotoStudio

$80.50

Would You Rather Premium Oversized Hoodie

Aleodor

$69.00

Stressed Raccoon What A Year This Week Has Been Premium Oversized Hoodie

d247

$69.00

Reapers Den beginning Lightweight Hoodie

ReapersDen

$41.99

Strength in Challenging Times Pullover Sweatshirt

qosshhawg47

$41.94

King Reap Pullover Sweatshirt

ReapersDen

$41.94

The Mycelium Labyrinth Premium Oversized Hoodie

Transelasticart

$69.00

Reapers Den ...The beginning Pullover Sweatshirt

ReapersDen

$41.94

Item preview, Dinosaurs Personalised Photo Jigsaw Puzzle Preserve Memories Custom Challenging Games Puzzle from Your Picture Wooden Puzzle Jigsaw designed and sold by MalakShams.

Dinosaurs Personalised Photo Jigsaw Puzzle Preserve Memories Custom Challenging Games Puzzle from Your Picture Wooden Puzzle Jigsaw Premium Oversized Hoodie

MalakShams

$69.00

football is life Premium Oversized Sweatshirt

fas166

$62.00

Challenging abstract Premium Oversized Sweatshirt

Aurora Murgescu

$56.84

Dance and f *** the rest Premium Oversized Hoodie

OlivierImages

$172.50

I Love Karachi Premium Oversized Hoodie

ZSA Futuristic Art

$66.13

challenging leadership for challenging times Premium Oversized Sweatshirt

popularculture

$60.45

I Am Afraid of Women Premium Oversized Sweatshirt

MDSDesigns

$67.17

It’s a process, not impossible Premium Oversized Hoodie

GlimmerAura

$63.25

Truth or dare Premium Oversized Hoodie

RoryRocket

$69.00

I am Challenging God Premium Oversized Sweatshirt

fabricsofteners

$62.00

challenging reality Premium Oversized Hoodie

wormink

$69.00

Challenging boxing Premium Oversized Sweatshirt

Txandrosan

$64.59

It Gets Worse Before It Gets Worse Frog Alligator Pessimism Humor Premium Oversized Hoodie

Doodleoub

$63.25

Challenging & Charming Premium Oversized Sweatshirt

Megan Volpert

$60.97

challenging cat Premium Oversized Hoodie

Mais80

$74.75

Challenging expectations Premium Oversized Sweatshirt

AngelArtss

$72.34

Otterly Challenging Premium Oversized Sweatshirt

ocean-friends

$62.00

You're challenging Premium Oversized Hoodie

livkelly

$64.98

Challenging enemies Premium Oversized Sweatshirt

ArtistTejal

$56.84

CHALLENGING CONVERSATIONS Premium Oversized Hoodie

Tadeusz1

$69.00

Challenging Look Premium Oversized Sweatshirt

F0R0G

$62.00

attractive villain Pullover Hoodie

TransDesign

$46.79

I'm retired funny saying Premium Oversized Sweatshirt

PDAG

$67.17

Consider the Impossible Premium Oversized Hoodie

BrandingNow

$69.00

Flaming sword Premium Oversized Hoodie

HappyHub03

$69.00

I Believe (In Nothing) Premium Oversized Hoodie

hidden-design

$69.00

Two faced alien Premium Oversized Hoodie

Bubblehavoc

$69.00

Stay Hard Premium Oversized Sweatshirt

ChangeNarrative

$59.42

I'm retired funny saying Premium Oversized Sweatshirt

PDAG

$67.17

Dead Cells Kill Die Learn Repeat Pullover Hoodie

Gabriela Mihai

$46.79

Stars: I Need My Space Premium Oversized Sweatshirt

Enhanceinner “Living The Life”

$62.00

GNARLY Premium Oversized Hoodie

HiddenStar02

$74.75

Tummy Ache Survivor Premium Oversized Hoodie

UrGo2Designs

$69.00

Funny Riddle which vehicle is spelled the same forwards and backwards RACECAR Premium Oversized Sweatshirt

Hohohaxi

$62.00

I've Been Through Premium Oversized Sweatshirt

oconghd

$67.17

I'm not challenging your authority Pullover Sweatshirt

THELOSTHOUSE

$45.44

thinking Chief tees Premium Oversized Sweatshirt

enerjik

$56.84

Gamer: I Need My Space Premium Oversized Hoodie

Enhanceinner “Living The Life”

$69.00

Every Family Needs Atleast 1 Redneck Premium Oversized Sweatshirt

Mad Over Store

$74.40

seductive logo Premium Oversized Sweatshirt

42youbest

$58.39

Three Kinds of Souls Premium Oversized Sweatshirt

NuminousYes

$67.17

A different perspective Premium Oversized Hoodie

kdraven

$63.25

May River Palmetto Bluff Golf Course South Carolina Premium Oversized Sweatshirt

William Holkham

$56.84

Do Your Best Funny Quote Premium Oversized Sweatshirt

ZSA Futuristic Art

$59.42

A quiet and mysterious corner. Premium Oversized Sweatshirt

Whose-sweat

$62.00

Great things Premium Oversized Hoodie

partsmanrod

$69.00

Pain Makes Gain Premium Oversized Sweatshirt

SuperJDkun

$62.00

Anime Biker Girl "Let's Race" Motorcycle Lightweight Hoodie

unboxedbyJuls

$38.49

Pipeline, Hawaii - Surf Premium Oversized Hoodie

Linbo Shop

$69.00

ART can be startling Premium Oversized Hoodie

Andykinoz

$74.75

Challenging The Undead In World Cup Finals Pullover Hoodie

minhdhbk

$42.89

Waimea Bay - Hawaii Premium Oversized Sweatshirt

Linbo Shop

$62.00

Pinochle night=best night! Premium Oversized Sweatshirt

Boardwalkmerch

$62.00

A quiet and mysterious corner. Premium Oversized Sweatshirt

Whose-sweat

$62.00

Do Not Sit Down Premium Oversized Hoodie

shassell2005

$69.00

Saint Philip Neri Premium Oversized Sweatshirt

anwil713

$62.00

A quiet and mysterious corner. Premium Oversized Hoodie

Whose-sweat

$69.00

Cloudbreak, Fiji - Surf Premium Oversized Sweatshirt

Linbo Shop

$62.00

Do Not Sit Down Premium Oversized Sweatshirt

shassell2005

$62.00

Find Your Peak Premium Oversized Hoodie

Phillips Pharms

$63.83

Merlin Rescue In Gemstone Premium Oversized Sweatshirt

Fearless-Fox

$64.59

Today's weakness are your upcoming strength Premium Oversized Hoodie

khaanju

$69.00

Surprising and original pattern Premium Oversized Hoodie

GAP90

$67.85

Banzai Pipeline, Hawaii - Surf Pullover Hoodie

Linbo Shop

$46.79

Freedom and oppression Premium Oversized Hoodie

MrFidelinchi

$69.00

Teahupo'o, Tahiti - Surf Premium Oversized Hoodie

Linbo Shop

$69.00

Fearless woman, challenging, confident woman, pop art style Premium Oversized Hoodie

RoryRocket

$69.00

I Identify As A Problem Sarcastic Humor Witty Personality Premium Oversized Sweatshirt

SofiBlair

$56.84

Today's weakness are your upcoming strength Premium Oversized Hoodie

khaanju

$69.00

Prepare For Trouble And Make It Double Premium Oversized Hoodie

Mad Over Store

$82.80

Dumpster Fire Response Team Chaos Humor Problem Solver Premium Oversized Hoodie

HumansStuck12

$103.50

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Clothing

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Challenging

Challenging hoodies and sweatshirts are expertly printed on ethically sourced, sweatshop-free apparel and available in a huge range of styles, colors and sizes. If you like your hoodies baggy, go two sizes up.

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Challenging Sweatshirts & Hoodies

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Secure Payments

Free Return

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