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Sailing School Hoodies

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Wiley's Sailing School Hoodie
Main Tag:  

Description: "Isn't this a breakthrough, that I'm a sailor? I sail? I sail now?" - Bob Wiley

Tags: baby steps, bill murray, boating, bob wiley, bob wileys sailing school

Wiley's Sailing School Hoodie

by Dustbrain Design

$32 $42

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Bob Wiley's Sailing School Retro Sunset Sailboat Hoodie
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Description: A circular emblem with horizontal stripes of yellow, orange, and red, depicting a sunset. Inside, a white sailboat is on water, with a dark tree line behind it. Above the emblem, text reads "BOB WILEY'S", and below, "SAILING SCHOOL EST. 1991". A white fish is at the top.

Tags: adventure, birds, boating, bob wileys, coastal

Bob Wiley's Sailing School Retro Sunset Sailboat Hoodie

by Birsencavus

$32 $42

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Bob Wiley's Sailing School - Since 1991 Hoodie
Main Tag:  

Description: Ahoy, I'm a sailor.

Tags: baby steps, bill murray, boat, caddyshack, dad

Bob Wiley's Sailing School - Since 1991 Hoodie

by BodinStreet

$32 $42

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Antipolis Sailing School Hoodie
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Description: We might not be the best school, but we ARE the other best school. Also, we're very close to the Giant Mistake, and that counts for something, doesn't it?

Tags: adventure, best school, boat, dnd5e, join the party

Antipolis Sailing School Hoodie

by jointheparty

$32 $42

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Traditional Tattoo Ship and sunset Homeward Bound Hoodie

Description: Traditional Tattoo Ship and sunset Homeward Bound

Tags: homeward bound, old school tattoo, sailing, sailing gift, sailing ship
Bob Wiley's Sailing School Hoodie
Main Tag:  

Description: Lake Winnipesaukee, NH Ahoy, I'm a sailor.

Tags: baby steps, bill murray, boat, dad, dont hassle me

Bob Wiley's Sailing School Hoodie

by BodinStreet

$32 $42

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Bob Wiley's Sailing School Ahoy Sailor Hoodie
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Description: Bob Wiley's Sailing School, Lake Winnipesaukee, since 1991. Ahoy, I'm a sailor!

Tags: adventure, boat, captain, lake, maritime

Bob Wiley's Sailing School Ahoy Sailor Hoodie

by ggraysondudley

$32 $42

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Bob Wiley's Sailing School - Lake Winnipesaukee, NH Hoodie
Main Tag:  

Description: Ahoy, I'm a sailor.

Tags: baby steps, bill murray, boat, caddyshack, dad

Bob Wiley's Sailing School - Lake Winnipesaukee, NH Hoodie

by BodinStreet

$32 $42

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Bob Wiley's Sailing School - Lake Winnipesaukee, NH Hoodie
Main Tag:  

Description: Bob Wiley's Sailing School - Lake Winnipesaukee, NH

Tags: baby steps, bill murray, boat, caddyshack, dad
Rough Waves Make A Skilled Sailor – Vintage Sailing Ship Graphic Tee Red Blue Hoodie
Main Tag:  

Description: Bold nautical graphic tee featuring a classic tall ship illustration paired with the motivational quote "Rough Waves Make A Skilled Sailor." Rendered in a striking red and navy two-tone style — perfect for sailors, sea lovers, and those who embrace life's challenges head-on. Vintage Americana meets old-school maritime grit.

Tags: boat lover, inspirational, maritime, motivational quote, nautical
Christopher Cross -  Retro Fan Design Hoodie

Description: Christopher Cross - Retro Fan Design

Tags: 70s, 70s pop culture, 70s style, 80s vintage, aor

Christopher Cross - Retro Fan Design Hoodie

by unknown_pleasures

$32 $42

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Rough Waves Make A Skilled Sailor – Vintage Sailing Ship Tee Hoodie
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Description: A bold vintage-style tee featuring a classic tall ship illustration with the powerful quote "Rough Waves Make A Skilled Sailor." Perfect for sailors, ocean lovers, and anyone who finds strength in life's challenges. Old-school tattoo aesthetic meets timeless motivation.

Tags: boat lover, inspirational, maritime, motivanional quote, nautical
Christopher Cross - Sailing - Original Retro Design Hoodie

Description: Christopher Cross - Sailing - Original Retro Design

Tags: 70s, 70s pop culture, 70s style, 80s vintage, aor

Christopher Cross - Sailing - Original Retro Design Hoodie

by unknown_pleasures

$32 $42

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Christopher Cross - Original Retro Fan Design Hoodie

Description: Christopher Cross - Original Retro Fan Design

Tags: 70s, 70s pop culture, 70s style, 80s vintage, aor

Christopher Cross - Original Retro Fan Design Hoodie

by unknown_pleasures

$32 $42

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Christopher Cross / Retro Aesthetic Fan Design Hoodie

Description: Christopher Cross / Retro Aesthetic Fan Design

Tags: 70s, 70s pop culture, 70s style, 80s vintage, aor music

Christopher Cross / Retro Aesthetic Fan Design Hoodie

by unknown_pleasures

$32 $42

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Captain of My Fate, Old School Nautical Sailing Ship Tattoo Hoodie
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Description: Distressed / vintage worn effect, old school / traditional style design with sailing ship. Text reads "Captain of My Fate, Master of My Destiny".

Tags: nautical tattoo, neo traditional tattoo, old school, old school tattoo, pinup girl
Christopher Cross - Sailing Hoodie

Description: Christopher Cross - Sailing - Original Retro Fan Design

Tags: 70s, 70s pop culture, 70s style, 80s vintage, aor

Christopher Cross - Sailing Hoodie

by unknown_pleasures

$32 $42

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I'm Local Hoodie
Main Tag:  

Description: Take a vacation from your problems

Tags: 90s, bill murray, bob wiley, comedy, humor

I'm Local Hoodie

by Dustbrain Design

$32 $42

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Sailor traditional tattoo Hoodie
Main Tag:  

Description: Cool, Unique, Classic

Tags: anchor, black and white, boat, monochrome, ocean

Sailor traditional tattoo Hoodie

by Abrom Rose

$32 $42

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TWO SIDED PRINT - FOREDECK UNION Hoodie
Main Tag:  

Description: COMMANDERS OF THE POINTY END! FOREDECK UNION NON-OFFICIAL UNION WEAR. Credit to Jennifer Fortuna Design for her graphics help!

Tags: boat, boating, foredeck, old school, pirate

TWO SIDED PRINT - FOREDECK UNION Hoodie

by MSR SALES

$32 $42

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The Ship Inside the Bottle – Vintage Nautical Tattoo Hoodie

Description: Some dreams are meant to travel, while others remain trapped in memory. The Ship Inside the Bottle is a dramatic vintage tattoo design featuring a magnificent three-masted sailing ship sealed inside a glass bottle. A mysterious skeleton sailor's hand rises from the ocean to hold it, surrounded by roses, rope, stars, a compass, and crashing waves. The banner “SOME DREAMS NEVER SAIL” adds a melancholy layer to this adventurous maritime scene. The combination of nautical romance and subtle macabre imagery makes the design feel like a forgotten piece of classic sailor flash discovered in an old tattoo shop. Bold black outlines, traditional colors, distressed texture, and strong graphic shapes make this ideal for vintage tattoo and maritime

Tags: compass tattoo, maritime art, nautical tattoo, ocean tattoo, old school
Dickie Greenleaf Sailing School Est. 1955 - modern vintage logo Hoodie

Description: Mongibello, Italy

Tags: bird, talented mr ripley, italian, italy, jude law
The Ship Inside the Bottle – Vintage Nautical Tattoo Hoodie

Description: Some dreams are meant to travel, while others remain trapped in memory. The Ship Inside the Bottle is a dramatic vintage tattoo design featuring a magnificent three-masted sailing ship sealed inside a glass bottle. A mysterious skeleton sailor's hand rises from the ocean to hold it, surrounded by roses, rope, stars, a compass, and crashing waves. The banner “SOME DREAMS NEVER SAIL” adds a melancholy layer to this adventurous maritime scene. The combination of nautical romance and subtle macabre imagery makes the design feel like a forgotten piece of classic sailor flash discovered in an old tattoo shop

Tags: compass tattoo, maritime art, nautical tattoo, ocean tattoo, old school
Traditional Tattoo Sailing Ship, Clipper Ship Illustration Hoodie

Description: Illustration depicting a clipper ship sailing in rough water, with traditional flowers, framed in a rope.

Tags: sailor, old school tattoo, sailboat, sailing, tattoo
Christopher Cross - Sailing - Original Retro Fan Design Hoodie

Description: Christopher Cross - Sailing - Original Retro Fan Design

Tags: 70s, 70s pop culture, 70s style, 80s vintage, aor

Christopher Cross - Sailing - Original Retro Fan Design Hoodie

by unknown_pleasures

$32 $42

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The Sailor Who Never Came Home – Vintage Nautical Tattoo Hoodie

Description: A hauntingly beautiful tribute to sailors, lost love, and the call of the sea. This vintage American traditional tattoo design features a lonely sailor standing beside a storm-battered lighthouse, holding a treasured letter while a tall sailing ship disappears into the distant horizon. Dramatic ocean waves, red roses, nautical rope, an anchor, and a weathered banner complete the composition. The artwork captures the emotional side of classic sailor tattoo culture: love, separation, loyalty, adventure, and the hope of returning home. Its bold black outlines, traditional red, mustard, green, cream, and muted blue palette give it the authentic character of old tattoo flash while the storytelling adds a deeper emotional connection.

Tags: lighthous, maritime, nautical tattoo, ocean lover, old school
Rose of the Seven Seas – Vintage Nautical Tattoo Hoodie
Main Tag:  

Description: Romance meets adventure in this richly detailed nautical tattoo design. At its center, a giant red rose grows from an antique compass while seven tiny sailing ships circle the flower like planets. Ocean waves, rope, stars, clouds, and a graceful swallow complete the composition. The banner “LOVE HAS NO HARBOR” gives the artwork a poetic emotional message about love that travels beyond distance, borders, and time. The combination of roses and nautical imagery creates a classic sailor tattoo aesthetic while the unusual composition gives the design its own identity. Perfect for sailors, romantics, ocean lovers, travelers, tattoo enthusiasts, and anyone who believes love is an adventure.

Tags: compass tattoo, love tattoo, nautical, nautical rose, ocean love
Rose of the Seven Seas – Vintage Nautical Tattoo Hoodie
Main Tag:  

Description: Romance meets adventure in this richly detailed nautical tattoo design. At its center, a giant red rose grows from an antique compass while seven tiny sailing ships circle the flower like planets. Ocean waves, rope, stars, clouds, and a graceful swallow complete the composition. The banner “LOVE HAS NO HARBOR” gives the artwork a poetic emotional message about love that travels beyond distance, borders, and time. The combination of roses and nautical imagery creates a classic sailor tattoo aesthetic while the unusual composition gives the design its own identity. Perfect for sailors, romantics, ocean lovers, travelers, tattoo enthusiasts, and anyone who believes love is an adventure

Tags: compass tattoo, intage tattoo, love tattoo, nautical, nautical rose
Education Is Important But Sailing Is Importanter - Sailing Lover Hoodie
Main Tag:  

Description: Education Is Important But Sailing Is Importanter

Tags: boat captain, boating gifts, boating season, education is important but sailing, funny sailing
The Harbor School Hoodie
Main Tag:  

Description: Retro 2000s TV reference. The Harbor School in Newport Beach shirt design.

Tags: 2000s, 2000s kids, 2000s pop culture, 2000s tv, california

The Harbor School Hoodie

by deadright

$32 $42

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The Last Voyage – Emotional Vintage Sailor Tattoo Hoodie
Main Tag:  

Description: The Last Voyage is a nostalgic tribute to goodbye, memory, and the endless pull of the sea. A tall sailing ship disappears toward a giant red sunset while a sailor's hand releases a single red rose into the waves. An old anchor wrapped in rope rests in the foreground as a lone swallow flies toward the horizon. The banner “ONE LAST VOYAGE” gives the design its emotional center, suggesting farewell, remembrance, and the courage to move forward. The dramatic composition is inspired by classic American traditional sailor tattoos but adds a cinematic sense of storytelling. Heavy black outlines, red, mustard, cream, dark green and muted blue, plus subtle distressed print texture create a timeless vintage tattoo appearance. Emotional vintage sailo

Tags: emotional tattoo, goodbye tattoo, last voyage, maritime, nautical tattoo
Eagle And Anchor - Traditional Americana Tattoo Hoodie
Main Tag:  

Description: Showcase classic American strength and maritime pride with this striking Eagle n Anchor splatter graphic. Featuring a fierce bald eagle gripping a heavy ship's anchor set against an aggressive, distressed red paint splatter background, this design draws heavy inspiration from traditional Americana and old-school military tattoo art. Executed in a crisp, high-contrast vector style with sharp edges and bold shading, it perfectly captures a rugged, unapologetic aesthetic. It is an ideal, mature statement piece for military veterans, maritime workers, tradesmen, and anyone who appreciates uncompromising vintage-inspired ink and classic American heritage.

Tags: american eagle, americana, anchor, eagle, navy veteran

Eagle And Anchor - Traditional Americana Tattoo Hoodie

by Brand X Graffix

$32 $42

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Wind Earns Respect From Every Sail Vintage Heritage Sport Tee Hoodie

Description: Conditions cannot be controlled, but they can be respected. "Wind Earns Respect From Every Sail." captures the spirit of endurance, adaptability, and resilience through classic heritage sport aesthetics and vintage typography.

Tags: 80s, 90s, athletic philosophy, endurance mindset, hand lettering apparel
Education Is Important But Sailing Is Importanter - Funny Sailing Hoodie
Main Tag:  

Description: Education Is Important But Sailing Is Importanter

Tags: boat engine, boating, boating funny, education is important but sailing, funny sailing
Kiss Of Love Hoodie

Description: Classic, Unique, Slang

Tags: vintage, old school, tattoo art, tattoo design, anchor

Kiss Of Love Hoodie

by Abrom Rose

$32 $42

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I Like Big Boats Hoodie

Description: More Sir Mix-A-Lot puns. A retro style illustration of a large sailing ship, the caption reads "I like big boats and I cannot lie"

Tags: drawing, old school, retro, sailor, ocean

I Like Big Boats Hoodie

by n23tees

$32 $42

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