Sailing Hats

Personalized

Design view

Safe search

Results updated

Custom

From $19.99

Trucker Hat

Add your own photo, logo or text

Customize →

Titanic Boat Vintage Cruise Ship Sailing in 1912 hit Iceberg Flat Bill Trucker Hat

$24.99

$29.99

Flat Bill Trucker Hat

Titanic Boat Vintage Cruise Ship Sailing in 1912 hit Iceberg

+7 more

Life Is Better On A Boat Sailboat Sketch Cool Sailing Gifts Flat Bill Trucker Hat

$24.99

$29.99

Flat Bill Trucker Hat

Life Is Better On A Boat Sailboat Sketch Cool Sailing Gifts

+7 more

Sea Turtle Hawaiian Honu Long Flexfit Unipanel Trucker Cap

$32.99

$39.99

Flexfit Unipanel Trucker Cap

Sea Turtle Hawaiian Honu Long

+8 more

Uss Liberty Agtr 5 Flexfit Unipanel Trucker Cap

$32.99

$39.99

Flexfit Unipanel Trucker Cap

Uss Liberty Agtr 5

+8 more

Block Island Ri Vintage Nautical Boat Anchor Flag Sports Gift Flat Bill Trucker Hat

$24.99

$29.99

Flat Bill Trucker Hat

Block Island Ri Vintage Nautical Boat Anchor Flag Sports Gift

+19 more

Montauk NY Vintage Crossed Oars & Boat Anchor Sports Hat

$19.99

$24.99

Trucker Hat

Montauk NY Vintage Crossed Oars & Boat Anchor Sports

+16 more

$19.99

$24.99

Trucker Hat

My Favorite Marine Calls Me Nana

+47 more

$19.99

$24.99

Trucker Hat

Funny Motor Boat Captain

+25 more

Cape Cod Ma Vintage Crossed Oars And Boat Anchor Sports Gift Yupoong Adult 5-Panel Trucker Hat

$29.99

$34.99

Yupoong Adult 5-Panel Trucker Hat

Cape Cod Ma Vintage Crossed Oars And Boat Anchor Sports Gift

+7 more

That's What I Do I Sail And I Know Things Boating Sailing Flexfit Unipanel Trucker Cap

$32.99

$39.99

Flexfit Unipanel Trucker Cap

That's What I Do I Sail And I Know Things Boating Sailing

+8 more

Door County Wi Vintage Nautical Boat Anchor Flag Sports Gift Yupoong Adult 5-Panel Trucker Hat

$29.99

$34.99

Yupoong Adult 5-Panel Trucker Hat

Door County Wi Vintage Nautical Boat Anchor Flag Sports Gift

+7 more

Heartbeat Sailing Sailboat Flexfit Unipanel Trucker Cap

$32.99

$39.99

Flexfit Unipanel Trucker Cap

Heartbeat Sailing Sailboat

+8 more

I'd Rather Be Sailing Vintage Sailing Hat

$19.99

$24.99

Trucker Hat

I'd Rather Be Sailing Vintage Sailing

+16 more

St. Tropez Summer Sailing Flat Bill Trucker Hat

$24.99

$29.99

Flat Bill Trucker Hat

St. Tropez Summer Sailing

+7 more

What Part Of Sailing Don't You Understand Captain Sailboat Flat Bill Trucker Hat

$24.99

$29.99

Flat Bill Trucker Hat

What Part Of Sailing Don't You Understand Captain Sailboat

+19 more

Sailboats On Open Water Nautical Theme Sailing Boating Gift Flexfit Unipanel Trucker Cap

$32.99

$39.99

Flexfit Unipanel Trucker Cap

Sailboats On Open Water Nautical Theme Sailing Boating Gift

+8 more

Vintage Boat Anchor Nautical Sailing Flat Bill Trucker Hat

$24.99

$29.99

Flat Bill Trucker Hat

Vintage Boat Anchor Nautical Sailing

+19 more

$19.99

$24.99

Trucker Hat

Sailing Dad

+47 more

Captain Sailing Boat Sailing Captain Yupoong Adult 5-Panel Trucker Hat

$29.99

$34.99

Yupoong Adult 5-Panel Trucker Hat

Captain Sailing Boat Sailing Captain

+3 more

Catalina Island Sailing Compass Rose Beach Boat Great Gift Flat Bill Trucker Hat

$24.99

$29.99

Flat Bill Trucker Hat

Catalina Island Sailing Compass Rose Beach Boat Great Gift

+19 more

Yes I have A Retirement Plan Sailing Flexfit Unipanel Trucker Cap

$32.99

$39.99

Flexfit Unipanel Trucker Cap

Yes I have A Retirement Plan Sailing

+8 more

Astronaut Moon Sailing Flat Bill Trucker Hat

$24.99

$29.99

Flat Bill Trucker Hat

Astronaut Moon Sailing

+19 more

Sprem Whale Sailing 7 Panel Mesh Trucker Snapback Hat

$32.99

$38.99

7 Panel Mesh Trucker Snapback Hat

Sprem Whale Sailing

Sailing Team Yupoong Adult 5-Panel Trucker Hat

$29.99

$34.99

Yupoong Adult 5-Panel Trucker Hat

Sailing Team

+7 more

Vintage Anchor Summer Sailing Design 7 Panel Mesh Trucker Snapback Hat

$32.99

$38.99

7 Panel Mesh Trucker Snapback Hat

Vintage Anchor Summer Sailing Design

Boston Massachusetts Souvenir Sailing Great Gift Hat

$19.99

$24.99

Trucker Hat

Boston Massachusetts Souvenir Sailing Great Gift

+47 more

$19.99

$24.99

Trucker Hat

Sail Vintage Sailing Boat

+47 more

$19.99

$24.99

Trucker Hat

Feelin Nauti Sailing Funny

+25 more

Sailing Funny Sailing Gangster Quote Sailor Sailboat Flexfit Unipanel Trucker Cap

$32.99

$39.99

Flexfit Unipanel Trucker Cap

Sailing Funny Sailing Gangster Quote Sailor Sailboat

+8 more

$19.99

$24.99

Trucker Hat

Sailing Retro Sail Boat

+47 more

Retro Sail Boat Sailing Graphic Flat Bill Trucker Hat

$24.99

$29.99

Flat Bill Trucker Hat

Retro Sail Boat Sailing Graphic

+19 more

Sailing Heartbeat For Sailors Flat Bill Trucker Hat

$24.99

$29.99

Flat Bill Trucker Hat

Sailing Heartbeat For Sailors

+7 more

Anchor Wanker Funny Sailing Boating Yupoong Adult 5-Panel Trucker Hat

$29.99

$34.99

Yupoong Adult 5-Panel Trucker Hat

Anchor Wanker Funny Sailing Boating

+3 more

Maritime Sailing Ship Sailing Ships Ships Compass Ship Ahoy Flat Bill Trucker Hat

$24.99

$29.99

Flat Bill Trucker Hat

Maritime Sailing Ship Sailing Ships Ships Compass Ship Ahoy

+19 more

First Mate Funny Anchor Sailing Ship Cruise Hat

$19.99

$24.99

Trucker Hat

First Mate Funny Anchor Sailing Ship Cruise

+47 more

You Might Also Be Interested In

About this collection

Find sailing hats in a variety of designs suited for everyday wear, gifts, and special occasions. Browse 305+ options and use filters to view styles like hoodies, hats, and mugs, or sort by newest, trending, and most popular. Each item is printed on demand with advanced printing technology for consistent quality and typically ships within 1–2 business days.

Explore Sailing Hats

Explore sailing hats created for gifts, events, and everyday wear. Whether you're browsing for a specific occasion or simply looking for a design that stands out, this page makes it easy to compare available options.

Find designs across different sizes, colors, and product styles, then sort by newest, trending, or most popular to narrow down your search. You can also use filters to discover related items like hoodies, hats, mugs, and more.

All products are printed on demand using advanced production equipment for consistent quality. Orders are usually produced quickly and typically ship within 1–2 business days.