Sailing Humor Caps

593 items

Yacht Rock Is My Therapy Baseball Cap

DesignsForThee

$25.19

Never Underestimate An Old Man Who Builds Model Ships In His Seventies Dad Hat

PosiMCreations

$25.19

Never Underestimate An Old Man Who Builds Model Ships In His Seventies Dad Hat

PosiMCreations

$25.19

Scurvy When Life Doesn't Give You Lemons - Vintage Pirate Ship Nautical Baseball Cap

Velustro Shop

$25.19

Piratecore Maritime Tall Ship Kraken Tentacles Graphic Baseball Cap

dragonwolfpack

$25.19

Captain Does What He Wants Vintage Baseball Cap

MWSailingClub

$24.14

Captain Does What He Wants Vintage Baseball Cap

MWSailingClub

$24.14

I Don't Know Vintage Anchor Quote Baseball Cap

MWSailingClub

$24.14

Boats Well With Others Funny Anchor Nautical Dad Hat

SiarheiYur

$32.11

Boats Well With Others Funny Nautical Sailing Design Dad Hat

SiarheiYur

$32.11

Shark Ship (version 1) Dad Hat

ales-panz

$23.09

Funny Anxious Steamboat Cartoon | Cute Boat Staying Afloat Meme Sticker Baseball Cap

MyxaART

$25.19

This Is Fine Funny Sailor Coffee Chaos Nautical Humor Design Baseball Cap

MonkiFlipp

$25.19

Boats Well With Others Funny Boating Captain Dad Hat

gunaone-design

$24.14

Let's Do Boat Stuff Funny Nautical Yachting Gift Dad Hat

gunaone-design

$24.14

I'll Be On The Boat Funny Nautical Baseball Cap

gunaone-design

$24.14

Awesome Captain Anchor Funny Nautical Boat Owner Baseball Cap

gunaone-design

$24.14

I Run A Tight Ship Wreck – Classic Sailing Badge Dad Hat

HumansStuck12

$31.49

I Run A Tight Ship Wreck – Vintage Coastal Adventure Dad Hat

HumansStuck12

$31.49

I Run A Tight Ship Wreck – Retro Sunset Sailing Scene Baseball Cap

HumansStuck12

$31.49

I Run A Tight Ship Wreck – Distressed Maritime Baseball Cap

HumansStuck12

$31.49

RUNNNNN | widow's bay Dad Hat

cadetgallery

$26.24

I Run A Tight Ship Wreck – Retro Sailing Disaster Edition Baseball Cap

RetroMini2026

$31.49

I Run A Tight Ship Wreck – Sunset Captain Chaos Baseball Cap

RetroMini2026

$31.49

I Run A Tight Ship Wreck – Vintage Ocean Liner Humor Dad Hat

RetroMini2026

$31.49

I Run A Tight Shipwreck Funny Nautical Sailing Captain Humor Baseball Cap

HumansStuck12

$31.49

I Run A Tight Ship Wreck Funny Nautical Sailing Humor Baseball Cap

HumansStuck12

$31.49

Prestige Worldwide Boats And Hoes Step Brothers Movie Boating Humor Baseball Cap

JonesFlora2025

$31.49

I Never Won a Blue Peter Badge Funny Sailing T-Shirt | British TV Nostalgia Graphic Tee Baseball Cap

GarnerSupplyCo

$25.19

More wind in retirement Dad Hat

pirminio

$26.24

Funny Cruise T-Shirt - Book Your Next Cruise With Us Shark Design Baseball Cap

RareVisuals

$25.19

The Revenge Of Whiskers Baseball Cap

Absurdo!

$23.09

Columbus World Tour Explorer Parody Baseball Cap

Retr0Tshirts

$25.19

Vasco da Gama World Tour Explorer Parody Baseball Cap

Retr0Tshirts

$25.19

Sea’s Call – Vintage Nautical Emblem Baseball Cap

Dogandesighn

$25.19

Wanker Anchor Self Deprecating Humor Joke Baseball Cap

TackyTime

$24.14

Scurvy When Life Doesn't Give You Lemons Funny Pirate Dad Dad Hat

GreggRoss

$25.19

Quann o Mare è Calmo — Neapolitan Dialect Vintage Print Naples Dad Hat

vesuviovibes

$25.19

Sailing Because Murder Is Wrong Funny Sailor Baseball Cap

StrideSuccess

$24.98

beggin' for a peggin' funny pirate offensive inappropriate Baseball Cap

cass-vale-lab

$25.19

Education Is Important But Sailing Is Importanter Dad Hat

GabbyKash

$25.19

North Coaster Lake Erie Life Bad Weather Bad Clothing Choices Quote Baseball Cap

YubitaLeLe

$26.24

Resentment Harbor Vintage Nautical Lighthouse Linocut Dad Hat

secondanchor

$25.19

The Captain Is Always Right I'm The Captain - Sunset Boat Captain Nautical Humor Baseball Cap

CutOutIdols

$25.19

The Captain Is Always Right I'm The Captain Dad Hat

CutOutIdols

$25.19

Feeling Nautical - Dark Version Dad Hat

PositronicStu

$23.09

Copy of I Run A Tight Shipwreck Summer Remembering My Why Dad Hat

gear-posters

$25.19

I Run A Tight Shipwreck Summer Remembering My Why Baseball Cap

gear-posters

$25.19

Surviving Thoughts Creative Mind Chaos Dad Hat

HumorInHues

$25.19

I'd Rather Be Sailing Dad Hat

WearFine

$23.09

Old Sailors Never Die, They Just Get a Little Dinghy Dad Hat

WearFine

$23.09

Sailing: Where You Spend a Fortune to Go Slowly Dad Hat

WearFine

$23.09

Vintage Sailor Captain Bearded Pipe Smoker Dad Hat

snowry

$24.14

Bermuda Triangle Survivor Club Vintage Nautical Mystery Baseball Cap

Amnesia-Proto

$25.19

Good Vibes Strong Winds – Sailing Monkey | Funny Nautical Zero Tolerance for Drama Design Dad Hat

MWSailingClub

$24.14

Sailing Dad Like a Normal Dad But Cooler – Vintage Sailboat Retro Nautical Gift for Fathers Baseball Cap

MWSailingClub

$24.14

Funny Cruise Vacation Quote Retro Sunset Cruise Ship Sticker Dad Hat

HungarianSailor

$23.09

I Don't Give A Ship - Funny 2026 Cruise Vacation Dad Hat

trendnest_shop

$23.09

“Abandon Ship” – Pirate Parrot Silhouette Design Baseball Cap

inallusha

$24.14

Sea Turtles Mate – Funny Pirate Quote – Ocean Humor Typography Design Baseball Cap

inallusha

$24.14

“To Freedom… To the Black Pearl” – Pirate Toast Rum Bottles Design Dad Hat

inallusha

$24.14

Coastal Print, Lake Hair, Boat Life Art, Lakeside Humor, Funny Art Dad Hat

Galleryinprint

$23.09

“Son, I’m Captain Jack Sparrow” – Pirate Quote Funny Typography Design Baseball Cap

inallusha

$24.14

“But Why Is the Rum Gone?” Pirate Quote – Drunken Sailor Silhouette Design Baseball Cap

inallusha

$24.14

Titanic Iceberg Vintage Parody Smooth Sailing Dad Hat

k3rstman1

$25.19

Funny Pirate Peg Leg Beggin For A Peggin Sarcastic Nautical Sailing Humor Dad Hat

Clyrexor

$25.19

You’re Oarsome Baseball Cap

Icareis-Studios

$25.08

Stay Salty Baseball Cap

Pier Pressure Baseball Cap

Icareis-Studios

$25.08

O-fish-ally Relaxed Dad Hat

Icareis-Studios

$25.08

Oar You Kidding Me Dad Hat

Let’s Get Nauti Dad Hat

Icareis-Studios

$25.08

Knot Bad at All Dad Hat

Good Vibes and High Tides Dad Hat

Icareis-Studios

$25.08

Feeling a Little Stern Dad Hat

Icareis-Studios

$25.08

Decked Out Baseball Cap

Icareis-Studios

$25.08

Buoyfriend Material Dad Hat

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Sailing Humor Caps

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