Challenge Sweatshirts & Hoodies

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1000+ items

3D Archery Archer Competition Tournament Gift Premium Oversized Hoodie

AndreasMei

$44.85

~~$74.75~~ (40% off)

3D Archery Archer Competition Tournament Gift Premium Oversized Hoodie

AndreasMei

$44.85

~~$74.75~~ (40% off)

3D Archery Archer Competition Tournament Gift Premium Oversized Hoodie

AndreasMei

$44.85

~~$74.75~~ (40% off)

3D Archery Archer Competition Tournament Gift Premium Oversized Hoodie

AndreasMei

$44.85

~~$74.75~~ (40% off)

3D Archery Archer Competition Tournament Gift Premium Oversized Sweatshirt

AndreasMei

$47.02

~~$67.17~~ (30% off)

3D Archery Archer Competition Tournament Gift Premium Oversized Hoodie

AndreasMei

$44.85

~~$74.75~~ (40% off)

3D Archery Archer Competition Tournament Gift Premium Oversized Sweatshirt

AndreasMei

$47.02

~~$67.17~~ (30% off)

Vintage Rubik's Cube Retro Colorful Puzzle Game Gift for Cube Enthusiasts Premium Oversized Hoodie

jamal alamri

$53.82

~~$89.70~~ (40% off)

Motivational You Can Do Anything for Seconds Inspirational Quote Design Premium Oversized Hoodie

AKIBAJARA

$53.82

~~$89.70~~ (40% off)

Eight Seconds of Courage Rodeo Bull Riding Inspiration Design Premium Oversized Hoodie

AKIBAJARA

$53.82

~~$89.70~~ (40% off)

Make Them Suffer - Bold Motivational Design for Strength and Resilience Premium Oversized Hoodie

DreamArtstore

$53.82

~~$89.70~~ (40% off)

Funny T-Rex Hates Push Ups Dinosaur Gym Workout Meme Premium Oversized Hoodie

Hilal-Studio

$37.95

~~$63.25~~ (40% off)

Item preview, You Are Stronger Than You Know T-Shirt | Life's Challenges Shape You Graphic Tee | Dark Motivational Skull Shirt designed and sold by vec4u.

You Are Stronger Than You Know T-Shirt | Life's Challenges Shape You Graphic Tee | Dark Motivational Skull Shirt Lightweight Hoodie

vec4u

$30.79

~~$38.49~~ (20% off)

Break Limits Not Yourself – Motivational Quote Premium Oversized Hoodie

the-dovlat

$39.68

~~$66.13~~ (40% off)

Natto Fermented Soybeans Superfood - Japanese Foodie Culture Pictogram Premium Oversized Hoodie

japan-picto

$41.40

~~$69.00~~ (40% off)

I'm Locked In Taskmaster Inspired Design for Fans of Challenge and Strategy Premium Oversized Hoodie

squaredesign

$53.82

~~$89.70~~ (40% off)

Does More With Less Five Watt Low Power Patch Premium Oversized Hoodie

BoosterShop

$41.40

~~$69.00~~ (40% off)

Bent Isn’t Broken – Resilience & Strength Motivational Quote Premium Oversized Sweatshirt

FaithArt777

$39.79

~~$56.84~~ (30% off)

Narrow Margin Inspirational Quote Motivational Typography Design Premium Oversized Hoodie

yungborrow

$53.82

~~$89.70~~ (40% off)

Hot Dog Eating Champion Fan Premium Oversized Hoodie

radson199

$41.40

~~$69.00~~ (40% off)

Munro Bagger Mountain Hiking Graphic Premium Oversized Hoodie

YarningsandYear

$41.40

~~$69.00~~ (40% off)

In Case of Emergency Break Rules Pullover Sweatshirt

Karate Octopus

$28.83

~~$38.45~~ (25% off)

NERVOUS AS A ZOMBIE AT QUIZ NIGHT Premium Oversized Sweatshirt

WheelieGdArt

$43.40

~~$62.00~~ (30% off)

Challenge You Quote Premium Oversized Hoodie

BostickirisArts

$41.40

~~$69.00~~ (40% off)

Lee Carvallo'S Putting Challenge Pullover Sweatshirt

DesignBlast

$31.45

~~$41.94~~ (25% off)

Turn Pressure Into Power Motivational Quote Premium Oversized Hoodie

the-dovlat

$39.68

~~$66.13~~ (40% off)

Ballerina Bass dBener Swan Pro Grace Lightweight Sweatshirt

Sitala Kiowa

$40.07

~~$53.42~~ (25% off)

Tiny Bass cBallerina Pro Star Premium Oversized Sweatshirt

Sitala Kiowa

$50.20

~~$71.72~~ (30% off)

Unmedicated Because I Like a Challenge Premium Oversized Hoodie

jkrphoto

$37.95

~~$63.25~~ (40% off)

Ballet Bass dRibbon Pro Elegance Premium Oversized Hoodie

Sitala Kiowa

$47.89

~~$79.81~~ (40% off)

Battle Royale Survival Program BR Emblem Laurel Wreath Premium Oversized Hoodie

kathrynsinor

$37.95

~~$63.25~~ (40% off)

Battle Royale Survival Program BR Emblem Laurel Wreath Premium Oversized Hoodie

Saraurnham

$37.95

~~$63.25~~ (40% off)

It's Never Too Spicy For Me Hot Sauce Chili Pepper Premium Oversized Hoodie

mari-kayden

$37.95

~~$63.25~~ (40% off)

Book Lovers Building a Reading Stack Premium Oversized Hoodie

Krasnovaovaova

$41.40

~~$69.00~~ (40% off)

Beyond mountains, there are mountains - Haiti proverb Premium Oversized Hoodie

Sketchplanations

$37.95

~~$63.25~~ (40% off)

Challenge the norm Premium Oversized Hoodie

Mind Empowerment Designs

$37.95

~~$63.25~~ (40% off)

Never Give Up Motivational Quote T-Shirt Premium Oversized Hoodie

Art Solom

$37.95

~~$63.25~~ (40% off)

Jolene You Can Have Him Premium Oversized Sweatshirt

johnsonliies

$50.64

~~$72.34~~ (30% off)

Lee Carvallo's Putting Premium Oversized Sweatshirt

Ribeiro-Art

$52.45

~~$74.92~~ (30% off)

Wade Challenges The Grim Reaper Premium Oversized Hoodie

DANILUMS

$37.95

~~$63.25~~ (40% off)

Big Challenges Alligator Premium Oversized Hoodie

evieguad

$50.03

~~$83.38~~ (40% off)

Big Challenges Premium Oversized Hoodie

evieguad

$50.03

~~$83.38~~ (40% off)

Tornado Trouble Adventure Game Inspired Design for Fans and Gamers Premium Oversized Hoodie

Prokop

$53.82

~~$89.70~~ (40% off)

Challenge Accepted New Beginning Embrace The Journey Mountain Wings Pullover Hoodie

Dravienart

$33.63

~~$44.84~~ (25% off)

Positive Thinking Premium Oversized Hoodie

ajkbilder

$41.40

~~$69.00~~ (40% off)

Watching a loading bar freeze at ninety-nine percent is a modern psychological challenge Premium Oversized Sweatshirt

English Learning

$39.79

~~$56.84~~ (30% off)

Ultimate Frisbee Premium Oversized Hoodie

ROSE ANN BANILAR

$51.75

~~$86.25~~ (40% off)

Stay Hard Lightweight Hoodie

dorothycmc

$30.79

~~$38.49~~ (20% off)

2026 Concept2 WOD Week Challenge Lightweight Hoodie

concept2inc

$33.59

~~$41.99~~ (20% off)

Baking Challenge Orange Creature Chef Premium Oversized Sweatshirt

toryshrops

$45.21

~~$64.59~~ (30% off)

The Horrors Persist But So Do I Perseverance Frog Endurance Premium Oversized Hoodie

HumansStuck12

$51.75

~~$86.25~~ (40% off)

Challenge Me Let's Play Karate Cat Premium Oversized Hoodie

Alaric4you

$37.95

~~$63.25~~ (40% off)

Challenge Accepted Wolf Premium Oversized Sweatshirt

calorula

$43.40

~~$62.00~~ (30% off)

Italo Disco Helped Me Survive 80s Challenges | Retro 80s Italian Disco Music Lover Gift Premium Oversized Sweatshirt

Graphroad

$43.40

~~$62.00~~ (30% off)

ADHD Empowerment Pop Art Illustration Premium Oversized Sweatshirt

PixlCrypt

$41.60

~~$59.42~~ (30% off)

Embrace Challenge Premium Oversized Hoodie

bolaAura

$37.95

~~$63.25~~ (40% off)

NEW YORK - The Hudson & Manhattan - Sprint & Swim - Oct. 10th 2026 Premium Oversized Sweatshirt

DBM Photo Art 1

$45.21

~~$64.59~~ (30% off)

Patrick Said But Who Listened Message Premium Oversized Sweatshirt

ImeldaSparks

$39.79

~~$56.84~~ (30% off)

Bead Tug Of War Champion Funny Competitive Game Design | ⭐⭐⭐⭐⭐ Premium Oversized Sweatshirt

DramaticTroll

$56.42

~~$80.61~~ (30% off)

Ultimate Stunt Race Champion Funny Jelly Bean Character Obstacle Course Party Game | ⭐⭐⭐⭐⭐ Pullover Hoodie

jamal alamri

$48.54

~~$64.72~~ (25% off)

Guess Ill Die Funny Gamer Gift | Perfect Gift For You And Friends Premium Oversized Hoodie

gyianas

$57.27

~~$95.45~~ (40% off)

Norse Axes Face Adversity Fight Harder Inspirational Premium Oversized Sweatshirt

rodkinsnscherre

$43.40

~~$62.00~~ (30% off)

Last Chemo Ring The Bell Run Like Hell Premium Oversized Hoodie

abenwaklimes

$41.40

~~$69.00~~ (40% off)

Item preview, Kpop Girl Group Aesthetic Signature Design Retro Y2K Inspired Fan Art Collectible | ⭐⭐⭐⭐⭐ Best Seller designed and sold by FunnyAftertaste.

Kpop Girl Group Aesthetic Signature Design Retro Y2K Inspired Fan Art Collectible | ⭐⭐⭐⭐⭐ Best Seller Premium Oversized Hoodie

FunnyAftertaste

$57.27

~~$95.45~~ (40% off)

I Love Karachi Premium Oversized Hoodie

ZSA Futuristic Art

$39.68

~~$66.13~~ (40% off)

You Are Disqualified Sarcastic Humor Rebellious Statement Premium Oversized Sweatshirt

JonesFlora2025

$54.25

~~$77.51~~ (30% off)

Doubts Limit Tomorrow Mountain Hikers Art Lightweight Hoodie

pankecibolay

$33.59

~~$41.99~~ (20% off)

Traitor Trump Flag Political Statement Premium Oversized Sweatshirt

cerima

$39.79

~~$56.84~~ (30% off)

Roblox Doors Hide And Seek | ⭐⭐⭐⭐⭐ Premium Oversized Hoodie

Prokop

$53.82

~~$89.70~~ (40% off)

Ten of Wands Tarot Card - Mystical Responsibility & Perseverance Illustration Premium Oversized Hoodie

ArcanaAbsolute

$41.92

~~$69.86~~ (40% off)

Under Estimate Me That'll Be Fun Empowerment Sarcasm Attitude Premium Oversized Sweatshirt

RetroMini2026

$54.25

~~$77.51~~ (30% off)

Challenge or Problem? Premium Oversized Sweatshirt

PeanutGalSean

$39.79

~~$56.84~~ (30% off)

Growth Takes Courage – Motivational Climbing Quote Design Premium Oversized Sweatshirt

v6ziix

$39.79

~~$56.84~~ (30% off)

Growth Takes Courage Motivational Climbing Quote Design Lightweight Sweatshirt

v6ziix

$31.76

~~$42.34~~ (25% off)

Growth Takes Courage Premium Oversized Sweatshirt

v6ziix

$39.79

~~$56.84~~ (30% off)

Growth Takes Courage – Motivational Climbing Quote Design Premium Oversized Hoodie

v6ziix

$37.95

~~$63.25~~ (40% off)

Growth Takes Courage Motivational Climbing Quote Design Premium Oversized Hoodie

v6ziix

$37.95

~~$63.25~~ (40% off)

Growth Takes Courage – Motivational Climbing Quote Design Premium Oversized Sweatshirt

v6ziix

$39.79

~~$56.84~~ (30% off)

I've been through 2026 - Nothing Scares Me Premium Oversized Sweatshirt

CreationsbYKz

$39.79

~~$56.84~~ (30% off)

Gamer Kids Playtime Fun | Awesome Gaming Gear | Limited Edition Premium Oversized Hoodie

MissRiahGames

$57.27

~~$95.45~~ (40% off)

Trails Are The New Highway Mountain Bike Design Premium Oversized Hoodie

jankelauv

$41.40

~~$69.00~~ (40% off)

Tough Mudder Distressed Runner Premium Oversized Sweatshirt

SilentCosmos

$43.40

~~$62.00~~ (30% off)

Become a member.Get 25% off your first order.Plus other neat perks and exclusive savings to help you find the very thing.

Clothing

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Challenge

Challenge 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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Challenge Sweatshirts & Hoodies

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