Challenging Sweatshirts & Hoodies

1000+ items

sisu Premium Oversized Hoodie

chuckleharski

$69.00

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

MillennialMemer

$77.63

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

MillennialMemer

$69.75

Dumpster Fire Response Team Chaos Humor Problem Solver Premium Oversized Hoodie

HumansStuck12

$86.25

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

GeniePixel

$69.00

PIECE OF SHIT FUCKING APP Premium Oversized Sweatshirt

Doogermann

$62.00

Challenging Cat Think Again Premium Oversized Hoodie

DetalleXL

$63.25

Challenging motivational quote Premium Oversized Sweatshirt

Duaxstudios11

$62.00

Young and challenging Pullover Sweatshirt

akrmsydra123

$41.94

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

Qzmet

$63.25

Coffee: Adulting Is Challenging Daily Premium Oversized Hoodie

FrankOliver

$63.25

challenging Premium Oversized Hoodie

artaniparis

$69.00

challenging Premium Oversized Hoodie

ninov94

$69.00

Challenging Lightweight Sweatshirt

NBento

$40.41

Would You Rather Premium Oversized Sweatshirt

Aleodor

$62.00

I'm not Challenging Premium Oversized Sweatshirt

ZenPhotoStudio

$72.34

Reapers Den beginning Lightweight Sweatshirt

ReapersDen

$46.19

King Reap Lightweight Sweatshirt

ReapersDen

$46.19

Strength in Challenging Times Premium Oversized Hoodie

qosshhawg47

$88.55

The Mycelium Labyrinth Premium Oversized Hoodie

Transelasticart

$69.00

Reapers Den ...The beginning Pullover Sweatshirt

ReapersDen

$41.94

Challenging abstract Premium Oversized Sweatshirt

Aurora Murgescu

$56.84

football is life Premium Oversized Sweatshirt

fas166

$62.00

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

Dance and f *** the rest Premium Oversized Hoodie

OlivierImages

$172.50

challenging leadership for challenging times Premium Oversized Sweatshirt

popularculture

$60.45

I Am Afraid of Women Premium Oversized Hoodie

MDSDesigns

$74.75

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

unboxedbyJuls

$42.34

I am Challenging God Premium Oversized Hoodie

fabricsofteners

$69.00

Truth or dare Premium Oversized Hoodie

RoryRocket

$69.00

It’s a process, not impossible Premium Oversized Sweatshirt

GlimmerAura

$56.84

Hidden Truth – Ethereal Ghost & Pastel Hearts Aesthetic Premium Oversized Hoodie

ANoelleART

$63.25

Today’s challenges pave the way for your future Premium Oversized Hoodie

Mountain-Point

$63.25

Challenging enemies Premium Oversized Sweatshirt

ArtistTejal

$56.84

challenging reality Premium Oversized Sweatshirt

wormink

$62.00

Challenging boxing Pullover Hoodie

Txandrosan

$48.74

Challenging & Charming Premium Oversized Sweatshirt

Megan Volpert

$60.97

CHALLENGING CONVERSATIONS Premium Oversized Hoodie

Tadeusz1

$69.00

Horse | Challenging Premium Oversized Hoodie

AhmedHelal8395

$69.00

Challenging Look Premium Oversized Sweatshirt

F0R0G

$62.00

challenging cat Premium Oversized Hoodie

Mais80

$74.75

Challenging expectations Premium Oversized Hoodie

AngelArtss

$80.50

Otterly Challenging Premium Oversized Sweatshirt

ocean-friends

$62.00

You're challenging Premium Oversized Sweatshirt

livkelly

$58.39

I'm retired funny saying Premium Oversized Hoodie

PDAG

$74.75

Two faced alien Premium Oversized Sweatshirt

Bubblehavoc

$62.00

Stay Hard Premium Oversized Hoodie

ChangeNarrative

$66.13

attractive villain Premium Oversized Sweatshirt

TransDesign

$62.00

I'm retired funny saying Premium Oversized Hoodie

PDAG

$74.75

vintage Premium Oversized Sweatshirt

pirminio

$69.75

Consider the Impossible Premium Oversized Hoodie

BrandingNow

$69.00

Flaming sword Premium Oversized Hoodie

HappyHub03

$69.00

vintage Premium Oversized Hoodie

pirminio

$77.63

Coffee Adulting Is Challenging Daily Tasks Premium Oversized Hoodie

FrankOliver

$63.25

I Believe (In Nothing) Premium Oversized Sweatshirt

hidden-design

$62.00

A different perspective Premium Oversized Sweatshirt

kdraven

$56.84

Three Kinds of Souls Premium Oversized Hoodie

NuminousYes

$74.75

Stars: I Need My Space Premium Oversized Hoodie

Enhanceinner “Living The Life”

$69.00

GNARLY Premium Oversized Sweatshirt

HiddenStar02

$67.17

I've Been Through Premium Oversized Sweatshirt

oconghd

$67.17

Tummy Ache Survivor Premium Oversized Hoodie

UrGo2Designs

$69.00

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

Hohohaxi

$69.00

Gamer: I Need My Space Premium Oversized Sweatshirt

Enhanceinner “Living The Life”

$62.00

thinking Chief tees Premium Oversized Sweatshirt

enerjik

$56.84

Every Family Needs Atleast 1 Redneck Premium Oversized Sweatshirt

Mad Over Store

$74.40

seductive logo Premium Oversized Sweatshirt

42youbest

$58.39

I'm not challenging your authority Premium Oversized Sweatshirt

THELOSTHOUSE

$67.17

Coffee Adulting Is Challenging Drinker Apparel Premium Oversized Sweatshirt

FrankOliver

$56.84

May River Palmetto Bluff Golf Course South Carolina Premium Oversized Sweatshirt

William Holkham

$56.84

Pipeline, Hawaii - Surf Premium Oversized Sweatshirt

Linbo Shop

$62.00

A quiet and mysterious corner. Premium Oversized Hoodie

Whose-sweat

$69.00

ART can be startling Pullover Hoodie

Andykinoz

$50.69

Pain Makes Gain Premium Oversized Hoodie

SuperJDkun

$69.00

Great things Premium Oversized Sweatshirt

partsmanrod

$62.00

Do Not Sit Down Premium Oversized Sweatshirt

shassell2005

$62.00

Waimea Bay - Hawaii Premium Oversized Hoodie

Linbo Shop

$69.00

A quiet and mysterious corner. Lightweight Sweatshirt

Whose-sweat

$46.19

Saint Philip Neri Lightweight Hoodie

anwil713

$41.99

Pinochle night=best night! Pullover Sweatshirt

Boardwalkmerch

$41.94

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

RoryRocket

$62.00

Freedom and oppression Premium Oversized Hoodie

MrFidelinchi

$69.00

Today's weakness are your upcoming strength Premium Oversized Sweatshirt

khaanju

$62.00

Banzai Pipeline, Hawaii - Surf Premium Oversized Hoodie

Linbo Shop

$69.00

Prepare For Trouble And Make It Double Premium Oversized Sweatshirt

Mad Over Store

$74.40

Teahupo'o, Tahiti - Surf Premium Oversized Sweatshirt

Linbo Shop

$62.00

Find Your Peak Premium Oversized Hoodie

Phillips Pharms

$63.83

Today's weakness are your upcoming strength Premium Oversized Sweatshirt

khaanju

$62.00

Do Not Sit Down Premium Oversized Hoodie

shassell2005

$69.00

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

d247

$56.84

Merlin Rescue In Gemstone Premium Oversized Hoodie

Fearless-Fox

$71.88

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Clothing

Sweatshirt

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

Worldwide Shipping

Secure Payments

Free Return

Local Support

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