Free shipping on orders over $99

•

Problem Hats

Results updated

Custom Trucker Hat
Custom

From $19.99

Trucker Hat

Add your own photo, logo or text

Customize →

Retired Drug Dealer Funny Recovery  Flexfit Unipanel Trucker Cap

$32.99

$39.99

Flexfit Unipanel Trucker Cap

Retired Drug Dealer Funny Recovery

+8 more
Michigan Great Lakes No Salt, No Sharks, No Problem Hoodie 7 Panel Mesh Trucker Snapback Hat

$32.99

$38.99

7 Panel Mesh Trucker Snapback Hat

Michigan Great Lakes No Salt, No Sharks, No Problem Hoodie

Inner Peace Begins With Four Words Not My Fking Problem Yupoong Adult 5-Panel Trucker Hat

$29.99

$34.99

Yupoong Adult 5-Panel Trucker Hat

Inner Peace Begins With Four Words Not My Fking Problem

Homer Alaska Drinking Town With A Fishing Problem Hat

$19.99

$24.99

Trucker Hat

Homer Alaska Drinking Town With A Fishing Problem

+47 more
Officially Retired 2026 Not My Problem Anymore Yupoong Adult 5-Panel Trucker Hat

$29.99

$34.99

Yupoong Adult 5-Panel Trucker Hat

Officially Retired 2026 Not My Problem Anymore

+7 more
You Gotta Problem With That Crabby Guy Hat

$19.99

$24.99

Trucker Hat

You Gotta Problem With That Crabby Guy

+25 more
My Drinking Team Has A Bowling Problem Flat Bill Trucker Hat

$24.99

$29.99

Flat Bill Trucker Hat

My Drinking Team Has A Bowling Problem

+19 more
Somebody's Problem Country Flat Bill Trucker Hat

$24.99

$29.99

Flat Bill Trucker Hat

Somebody's Problem Country

+19 more
Its Me Hi I'm the Problem Its Me Hat

$19.99

$24.99

Trucker Hat

Its Me Hi I'm the Problem Its Me

+16 more
Possum Don't Be Part Of The Problem Be The Whole Problem Flat Bill Trucker Hat

$24.99

$29.99

Flat Bill Trucker Hat

Possum Don't Be Part Of The Problem Be The Whole Problem

+7 more
Golfing Problem  Flat Bill Trucker Hat

$24.99

$29.99

Flat Bill Trucker Hat

Golfing Problem

+19 more
Problem Solved Flat Bill Trucker Hat

$24.99

$29.99

Flat Bill Trucker Hat

Problem Solved

+7 more
I Don't Have An Attitude Problem You Have A Perception Problem 7 Panel Mesh Trucker Snapback Hat

$32.99

$38.99

7 Panel Mesh Trucker Snapback Hat

I Don't Have An Attitude Problem You Have A Perception Problem

You Might Also Be Interested In

About this collection

Browse problem hats designed for everyday wear, gifts, and special occasions. Choose from 317+ options and use filters to explore other styles like hoodies, hats, mugs and more, or sort by newest, trending, and most popular. Each item is printed on demand using state-of-the-art equipment for high-quality results and typically ships within 1–2 business days.

Problem Hats Collection

Discover problem hats designed for everyday wear, awareness events, and meaningful gifts. Whether you're shopping for yourself or looking for something special, this collection offers designs that highlight personal style and purpose.

Choose from a wide range of styles including bold graphics, minimalist designs, and classic looks. Our hats are available in multiple sizes, colors, and fits to match your preferences and ensure all-day comfort.

Looking for more options? Explore this design across other styles like hoodies, hats, mugs and more to find the perfect match. Every item is printed on demand using advanced printing technology for high-quality results and typically ships within 1–2 business days.

Sign Up For Our Newsletter

Receive 10% Off Your First Order & Discounts in your inbox every week!

[email protected]

Monday-Friday
10:00 AM - 5:00 PM EST

21440, Melrose Ave.
Southfield, MI 48075