FIRST DIBS: 25% Off Pillows | Up to 50% Sitewide
Ends in:
1 day
12h
3m
40s
Shop Now
Sell your art
Login
Signup
Caps
Retro mountain with trees
Redbubble logo
Explore
For You
Retro Gaming
Horror
Sci-Fi
80s Fandoms
Pop-Culture
Fresh Finds
Fan Art
Blockbuster Movies
Clothing
New
All Clothing
T-Shirts
New
Hoodies & Sweatshirts
Hats
New
Socks
Dresses
Tank Tops
Stickers
All Stickers
Holographic Stickers
Funny Stickers
Car Stickers
Bumper Stickers
Water Bottle Stickers
Cool Stickers
Anime Stickers
Laptop Stickers
Magnets
Custom Stickers
Phone Cases
All Phone Cases
iPhone Cases
Samsung Galaxy
New
Wall Art
All Wall Art
Posters
Photographic Prints
Art Prints
Tapestries
Canvas Prints
Framed Prints
Home & Living
All Home & Living
Mugs
Throw Pillows
Throw Blankets
Tapestries
Magnets
Aprons
Coasters
Jigsaw Puzzles
Acrylic Blocks
Kids & Babies
All Kids Clothes
Kids T-Shirts
Baby One-Pieces
Kids Pullover Hoodies
Accessories
All Accessories
Hats
New
Socks
Pins
Tech Accessories
Tote Bags
Zipper Pouches
Stationery & Office
All Stationery & Office
Greeting Cards
Spiral Notebooks
Mouse Pads & Desk Mats
Postcards
Hardcover Journals
Gifts
All Gifts
Gifts for Book Lovers
Gifts for Gamers
Gifts for Her
Gifts for Him
Gifts for Animal Lovers
Gifts Under $50
Gifts for Outdoorsy Types
Gifts for Kids
Stocking Stuffers
Gift Cards
Questionable Choices Caps
146 items
Hats
Filters (2)
146 items
Most Relevant
Questionable Choices Trucker Hat
Fanverse Merchandise
$19.19
$23.99
(20% off)
Moral Compass Slightly Askew Trucker Hat
clusefromcuse
$17.59
$21.99
(20% off)
I main morally questionable choices in RPGs Trucker Hat
Ninjacatoff
$19.19
$23.99
(20% off)
I main morally questionable choices in RPGs Trucker Hat
Ninjacatoff
$19.19
$23.99
(20% off)
I main morally questionable choices in RPGs Dad Hat
Ninjacatoff
$20.15
$25.19
(20% off)
I main morally questionable choices in RPGs Baseball Cap
Ninjacatoff
$20.15
$25.19
(20% off)
Headed Out To Make Some Questionable Choices Skeleton Funny Sarcastic Quote Dad Hat
Per My Last Nerve Studio
$20.15
$25.19
(20% off)
Lemur – My Entire Life Is Questionable Decisions Dad Hat
lazydogonline
$18.47
$23.09
(20% off)
Making Questionable Choices Baseball Cap
theartfulaspie
$20.15
$25.19
(20% off)
so Thankful My Best Friend Chose me Questionable Life Choice Trucker Hat
LittleDame
$19.19
$23.99
(20% off)
Department Of Bad Decisions Funny Sarcastic Adult Humor Dad Hat
HumansStuck12
$25.19
$31.49
(20% off)
Fueled by pizza and questionable life choices Baseball Cap
Ninjacatoff
$20.15
$25.19
(20% off)
Fueled by pizza and questionable life choices Trucker Hat
Ninjacatoff
$19.19
$23.99
(20% off)
Running on caffeine, chaos, and questionable choices Baseball Cap
Aetheriswork
$20.15
$25.19
(20% off)
Questionable Bold Comic Word Art Dad Hat
RedCircleArt
$18.64
$23.30
(20% off)
Powered By Questionable Choices Trucker Hat
TrendHooper
$17.75
$22.19
(20% off)
Oops, The risk I took was calculated but man am I bad at math Dad Hat
Right-Brain
$18.47
$23.09
(20% off)
Cute Face Questionable Choices Trucker Hat
theartfulaspie
$19.19
$23.99
(20% off)
Captain of Questionable Choices Trucker Hat
DemureArtsy
$19.19
$23.99
(20% off)
Caffeine and Questionable Choices Dad Hat
2Kousins
$18.47
$23.09
(20% off)
Emotionally Tired Caffeinated AF T-Shirt Baseball Cap
SubStudio97
$25.19
$31.49
(20% off)
Defending Against Questionable Fashion Choices Dad Hat
Owcomm
$20.15
$25.19
(20% off)
We’ll Make a Questionable Decision When the Time Comes Funny Sarcastic Quote Baseball Cap
inkoutninja
$20.15
$25.19
(20% off)
Powered By Wi-Fi & Questionable Life Choices - Funny Tech Tee Dad Hat
Merchifyme2000
$18.47
$23.09
(20% off)
So Thankful My Best Friend Chose Me Questionable Life Baseball Cap
Voidbinder
$20.15
$25.19
(20% off)
Questionable Decisions Funny Retro Stamp Design Dad Hat
EastEndTownie
$19.31
$24.14
(20% off)
Tired Coffee Cup Runs on Poor Decisions Baseball Cap
WildLeafDigital
$18.47
$23.09
(20% off)
One Poor Decision from Greatness Dad Hat
Itouchedabee
$20.15
$25.19
(20% off)
Bad Decisions Incoming Baseball Cap
Chill Doodles
$20.15
$25.19
(20% off)
Festive sock, questionable life choices Baseball Cap
Peerless-Prime
$50.37
$62.97
(20% off)
Pumpkin Spice & Questionable Life Choices Trucker Hat
Nikki Krishna
$19.19
$23.99
(20% off)
Contains: Souvenirs & Questionable Fashion Choices Trucker Hat
tropicaltee
$19.19
$23.99
(20% off)
Institute Of Questionable Life Choices Baseball Cap
PictorialWhimsy
$20.15
$25.19
(20% off)
Angetrieben von Sarkasmus und fragwürdigen Lebensentscheidungen | Handwritten-style Font Baseball Cap
RM-Journey
$18.47
$23.09
(20% off)
it seemed like a good idea at the time Dad Hat
101univers
$20.15
$25.19
(20% off)
Fueled by sarcasm and questionable life choices | Handwritten-style Font Trucker Hat
RM-Journey
$17.59
$21.99
(20% off)
Good Raising Questionable Decisions – Funny Southern Saying Trucker Hat
lecroyhouse
$17.59
$21.99
(20% off)
Good At Making Bad Decisions Funny Humor Relatable Quote Dad Hat
HumansStuck12
$25.19
$31.49
(20% off)
Thanks For Being Friends With Me Questionable Life Choice Dad Hat
Tatianamiobi
$20.15
$25.19
(20% off)
That's A Horrible Idea What Time? Sarcasm Humor Adventurous Quote Dad Hat
JonesFlora2025
$26.87
$33.58
(20% off)
so Thankful My Best Friend Chose me Questionable Life Choice Trucker Hat
ConceptThena
$19.19
$23.99
(20% off)
Bad Idea Club Vintage Retro Aesthetic Humor Design | Best Gift Dad Hat
netriic
$26.03
$32.54
(20% off)
Soft Heart Questionable Choices Gay Humor Trucker Hat
Neofly.Art
$18.39
$22.99
(20% off)
Powered By Snacks Questionable Choices Retro Trucker Hat
Mr Lee
$18.39
$22.99
(20% off)
Tide Pods Dad Hat
Naux | Design & Illustration
$27.70
$34.63
(20% off)
Glitter, Chaos, and Questionable Life Choices Baseball Cap
theartfulaspie
$20.15
$25.19
(20% off)
Powered by Questionable Decisions Baseball Cap
Picturit
$20.15
$25.19
(20% off)
The Best Cigarette After a Disastrous Decision Baseball Cap
Makebashington
$21.83
$27.29
(20% off)
Making for Thanksgiving - Questionable Carving Choices Baseball Cap
ArtitudePrintLb
$20.15
$25.19
(20% off)
Been There Done That Questionable Choices Dad Hat
SecretSquirrellDesigns
$18.47
$23.09
(20% off)
Department of Bad Decisions Repeat Offender Funny Vintage Shirt No Regrets Tee Trucker Hat
GhostDawgs
$21.59
$26.99
(20% off)
That's A Horrible Idea What Time Trucker Hat
101univers
$19.19
$23.99
(20% off)
Choose One – Department of Questionable Affairs Baseball Cap
Bad Taste Department
$18.47
$23.09
(20% off)
MASTER OF QUESTIONABLE LIFE CHOICES - Funny Humor Design, Relatable Sarcastic Art, Perfect Gift for Brother, Sister, Friend, Family, or Party Humor Baseball Cap
love3617
$20.15
$25.19
(20% off)
2026 The Year of Questionable Choices Funny New Year Dad Hat
BlissHalo
$18.47
$23.09
(20% off)
Ready for a Day of Questionable Choices Baseball Cap
Design Delinquent
$20.15
$25.19
(20% off)
surviving on sarcasm and questionable life choices Baseball Cap
rawaart1
$20.99
$26.24
(20% off)
surviving on sarcasm and questionable life choices Dad Hat
rawaart1
$20.99
$26.24
(20% off)
Fueled By Coffee and Questionable Life Choices Trucker Hat
whimsyswan
$17.59
$21.99
(20% off)
Caffeine, Chaos & Life Choices Skeleton Trucker Hat
Bluntdivas
$19.19
$23.99
(20% off)
Warning Poor Decision Making Dad Hat
Nol1ytv
$18.47
$23.09
(20% off)
Fueled By Caffeine And Questionable Life Choices. Dad Hat
Megaera8
$20.99
$26.24
(20% off)
Running on caffeine and questionable life choices. Baseball Cap
Anxiety.
$21.83
$27.29
(20% off)
Powered By Caffeine Questionable Choices Birthday Gift Dad Hat
Say It With Ink
$20.15
$25.19
(20% off)
Professional Collector Of Bad Ideas – Funny Crow Retro Cartoon Dad Hat
NarpLTD
$20.15
$25.19
(20% off)
A Terrible Idea Funny Banana Design Trucker Hat
MonkiFlipp
$19.19
$23.99
(20% off)
Alcohol: Makes bad decisions sound like good ideas. Dad Hat
onicaras
$20.15
$25.19
(20% off)
Running on caffeine and questionable life choices. | Handwritten-style Font Dad Hat
RM-Journey
$18.47
$23.09
(20% off)
Bad Decisions Department Graffiti Design Baseball Cap
Nol1ytv
$18.47
$23.09
(20% off)
Howdy Hot Mess – Funny Black Cat Cowboy Western Humor Baseball Cap
Kawaii-n-Spice
$20.15
$25.19
(20% off)
Good Food, Tan Lines, and Questionable Choices Funny Summer Quote Baseball Cap
Jollys-ArtShop
$20.15
$25.19
(20% off)
Pumpkin Spice, Spooky Nights & Questionable Choices – Funny Halloween Design Dad Hat
NViora
$18.47
$23.09
(20% off)
Tomato Tempest & the Doorway of Questionable Life Choices Dad Hat
Print Fiction
$20.15
$25.19
(20% off)
Honk If You've Made Questionable Choices - Silly Goose Dad Hat
LoveLabDesign
$21.83
$27.29
(20% off)
The 1920s Hot Jazz and Questionable Life Choices Baseball Cap
BdawgsFactory
$18.47
$23.09
(20% off)
Surviving Off Spite Caffeine And Questionable Life Choices Dad Hat
Sovereign Supply Co.
$20.99
$26.24
(20% off)
Cute Funny Frog Questionable Life Choices Meme Art Trucker Hat
ArtivoNest
$17.59
$21.99
(20% off)
Caffeine, Chaos, And Questionable Life Choices! - Office Humor Dad Hat
SSustainable
$23.51
$29.39
(20% off)
Surviving Off Spite Caffeine And Questionnaires Decisions Baseball Cap
Sovereign Supply Co.
$20.99
$26.24
(20% off)
Bad Decision Humor – It Escalated Quickly Baseball Cap
No Excuses Supply
$20.15
$25.19
(20% off)
My choices demonstrate an ominously questionable moral compass Baseball Cap
Click-Like
$20.15
$25.19
(20% off)
My choices demonstrate an ominously questionable moral compass Dad Hat
Click-Like
$20.15
$25.19
(20% off)
Bad Example – Funny Self Awareness Dad Hat
CleanDecor
$20.15
$25.19
(20% off)
Fueled By Snacks & Questionable Choices - Humorous Foodie Tee Dad Hat
Merchifyme2000
$18.47
$23.09
(20% off)
Kitch – Retro Maximalist Design for the Bold and Ironic Baseball Cap
ReggieDior
$20.15
$25.19
(20% off)
So Thankful My Best Friend Chose me Questionable Life Choice Baseball Cap
Voidbinder
$20.15
$25.19
(20% off)
Become a member.
Get 25% off your first order.
Plus other neat perks and exclusive savings to help you find the very thing.
Sign up
Previous
1
2
Next
Funny
Funny Quote
Sarcasm
Humor
Bad Decisions
Sarcastic
Animated Funny Animal Shirts
Cheering Up Gifts
Funny Cowork Gift
Questionable
Questionable Life Choices
Sarcastic Quote
Relatable Humor
Worldwide Shipping
Available as standard or express delivery
Learn more
- opens in new window or tab
Secure Payments
100% Secure Payment with 256-bit SSL encryption
Learn more
- opens in new window or tab
Free Return
Exchange or money back guarantee for all orders
Learn more
- opens in new window or tab
Local Support
24/7 Dedicated support
Learn more
- opens in new window or tab