Churchill Hats

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1000+ items

Winston Churchill Never Surrender Dad Hat

Rowephoeniart

$23.09

If You’re Going Through Hell Just Keep Going Dad Hat

SarahJosArt

$23.09

Inspiring Winston Churchill Never Give In Quote Bucket Hat

Owcomm

$26.94

Louisville Kentucky USA Line Art Landmark Poster Baseball Cap

CMYKStudio

$25.19

Winston Churchill Portrait With British Flag Bucket Hat

Owcomm

$26.94

Winston Churchill Portrait With A Cigar Dad Hat

Owcomm

$25.19

Churchill Rocker Guitar Stencil Worn Look Bucket Hat

OLIVIPAYSINGER

$26.94

Sir Winston Churchill Bucket Hat

brittamyradq

$26.94

Winston Churchill Up The Boro 1 Baseball Cap

alexusarena

$25.19

Winston Churchill Portrait With Cigar Illustration Bucket Hat

Owcomm

$26.94

CHURCHILL Baseball Cap

javitennis

$25.19

Wapusk National Park Canada Vintage Travel Bucket Hat

TravelersGems

$29.19

Manitoba Canada Hudson Bay Coast Polar Bear Vintage Patch Dad Hat

LittleArij

$25.19

Item preview, Winston Churchill Poster, Vintage Propaganda Wall Art, Retro Pop Art Print, British History Decor designed and sold by ValentinaHramov.

Winston Churchill Poster, Vintage Propaganda Wall Art, Retro Pop Art Print, British History Decor Baseball Cap

ValentinaHramov

$28.34

Winston Churchill Poster, Vintage Propaganda Wall Art, Retro Pop Art Print, British History Decor Baseball Cap

ValentinaHramov

$28.34

Churchill Aurora Borealis Ragdoll Badge: Chase Aurora Baseball Cap

MossyAndPearl

$26.24

Come Dancing racehorse - no backround Baseball Cap

Carmen Jimenez

$25.19

Come Dancing racehorse - with backround Baseball Cap

Carmen Jimenez

$25.19

Top Hat Man Cigar Peace Sign Circular Emblem Dad Hat

japaneseartist

$25.19

Phillip Island Victoria with Penguin Parade, Nobbies and Coastal Wildlife Dad Hat

Aryabek

$27.92

Item preview, 8355-1 "Courage Is What It Takes To Stand Up And Speak; Courage Is Also What It Takes To Sit Down And Listen." ..Winston Churchill (1874-1965): Sapien Collection designed and sold by ItzaCooper.

8355-1 "Courage Is What It Takes To Stand Up And Speak; Courage Is Also What It Takes To Sit Down And Listen." ..Winston Churchill (1874-1965): Sapien Collection Bucket Hat

ItzaCooper

$24.70

America 250 Kentucky Derby T-Shirt | Louisville Horse Racing Patriotic 1776-2026 Tee v4 Bucket Hat

DarylWelsh2024

$29.19

America 250 Kentucky Derby T-Shirt | Louisville Horse Racing Patriotic 1776-2026 Tee v3 Baseball Cap

DarylWelsh2024

$27.29

America 250 Kentucky Derby T-Shirt | Louisville Horse Racing Patriotic 1776-2026 Tee v2 Baseball Cap

DarylWelsh2024

$27.29

France Map Petit Palais Golden Gate Paris Silhouette Baseball Cap

Maroan93

$23.09

Churchill Polar Bear - Flat Vector Wildlife Art Bucket Hat

ZUMERI

$26.94

winston churchill playing electric guitar rocker performance Bucket Hat

Layan Shehab

$26.94

America 250 Kentucky Derby T-Shirt | Louisville Horse Racing Patriotic 1776-2026 Tee v1 Baseball Cap

DarylWelsh2024

$27.29

British Winston Churchill Countryball Cartoon Baseball Cap

Torket-y

$22.04

Churchill Downs Racetrack Watercolor Dad Hat

ChemicalXShop

$27.29

I Love Winston Churchill Baseball Cap

shitpostee

$27.29

MK IV Churchill Tank Dad Hat

HillC1985

$23.09

Churchill Downs Horse Wind Vain Bucket Hat

Dlt1981

$25.82

W. Churchill Baseball Cap

Chamberskid

$23.09

Magnitude Wins The Stephen Foster Stakes horse racing dsign Baseball Cap

Ginny Luttrell

$25.19

Item preview, Funny English Bulldog Winston Churchill Quote | Success Motivation Dog Art | Inspirational Bulldog Design designed and sold by Donsean22.

Funny English Bulldog Winston Churchill Quote | Success Motivation Dog Art | Inspirational Bulldog Design Bucket Hat

Donsean22

$24.70

Item preview, Winston Churchill Success Quote Silhouette | Inspirational Motivation Typography | Failure to Success Art designed and sold by Donsean22.

Winston Churchill Success Quote Silhouette | Inspirational Motivation Typography | Failure to Success Art Bucket Hat

Donsean22

$24.70

Darkest Hour Retro Winston Churchill WWII Drama Tribute Art Movie Poster Dad Hat

Art's Diner

$23.09

Retro Style 2026 Stephen Foster Stakes Horse Racing Design for Gifts Baseball Cap

Ginny Luttrell

$25.19

Winston Churchill Graffiti Artwork in Brighton Baseball Cap

Radiocafe

$25.19

Still Hate Churchill Bucket Hat

Seorai

$26.94

Blenheim Palace Estate and Marlborough Heritage England Baseball Cap

Places On Earth

$28.34

Kentucky State Flag KY Dad Hat

shitpostee

$27.29

Winston Churchill Playing Electric Guitar Dad Hat

kennedy-brook

$25.19

Not Dead Yet Bucket Hat

Teerlinck

$24.70

Churchill Motorcycle Rider biker funny history humor Baseball Cap

snowry

$24.14

Winston Churchill Running funny history runner Bucket Hat

snowry

$25.82

Churchill guitarist funny history guitar player Dad Hat

snowry

$24.14

Churchill fisherman fishng funny history fan Bucket Hat

snowry

$25.82

Churchill Deadlift Workout funny history fan gym Dad Hat

snowry

$24.14

Winston Churchill Archer Bow Hunter funny history fan Baseball Cap

snowry

$24.14

Churchill Retro arcade gamer funny Bucket Hat

snowry

$25.82

Churchill Music logo Bucket Hat

ChurchillScool

$24.70

Strade B Bar at Churchill School Bucket Hat

ChurchillScool

$24.70

Churchill Head Badge logo Baseball Cap

ChurchillScool

$23.09

Derby Royalty Since 1875 Baseball Cap

LyssasMindArt

$23.09

Vintage Louisville Kentucky Gateway to the South Skyline Dad Hat

k3rstman1

$25.19

Winston Churchill Playing Electric Guitar Rocker Humor Bucket Hat

schoolofbullies

$26.94

Roses & Racing Dad Hat

LyssasMindArt

$23.09

Golden Tempo 2026 Kentucky Derby 152 horse racing design Bucket Hat

Ginny Luttrell

$26.94

Always A Runner 2026 Kentucky Oaks 152 horse racing design on apparel and more Bucket Hat

Ginny Luttrell

$26.94

Kentucky Derby The Run for the Roses Dad Hat

The Art Queen Of Michigan

$31.49

Kentucky Derby - Golden Tempo wins the 152nd Kentucky Derby Baseball Cap

DBM Photo Art 1

$26.24

Kentucky Derby Winner - Golden Tempo - 152nd Kentucky Derby Baseball Cap

DBM Photo Art 1

$26.24

Golden Tempo Wins 152nd Kentucky Derby - Saturday, May 2, 2026 Bucket Hat

DBM Photo Art 1

$28.06

The Original Kentucky Derby Churchill Downs Baseball Cap

The Art Queen Of Michigan

$31.49

Golden Tempo - Winner of the 152nd Kentucky Derby152nd Bucket Hat

DBM Photo Art 1

$28.06

2026 Kentucky Oaks152 Horse Racing Design on apparel and more Baseball Cap

Ginny Luttrell

$25.19

Wapusk National Park Canada Dad Hat

NPStudio

$23.09

Kentucky Derby Time Bucket Hat

WoodburyLake

$26.45

Kentucky Derby Time Baseball Cap

WoodburyLake

$25.12

Kentucky Derby Time Bucket Hat

WoodburyLake

$26.45

Winston Churchill Playing Electric Guitar Baseball Cap

CallDesign

$27.29

Winston Churchill Playing Electric Guitar Rocker Humor Baseball Cap

first-shirt ⭐ ⭐ ⭐ ⭐ ⭐

$25.19

Manitoba Canada Map Mascot - Cute Polar Bear & Northern Lights Bucket Hat

Travel.Art

$24.70

And They’re Off Derby Day Dad Hat

Antdoodle

$25.19

Kentucky Derby 152 Run For The Roses 2026 Vintage Baseball Cap

EvrmoodCo

$23.09

I Love Winston Churchill Bucket Hat

shitpostee

$29.19

Kentucky Derby 2026 - The Run for the Roses - Kyderby Baseball Cap

legbabella

$25.19

Kentucky Derby 2026 - The Most Exciting Two Minutes in Sports at Churchill Downs Dad Hat

legbabella

$25.19

Kentucky Derby 2026 - The Run for the Roses at Churchill Downs Bucket Hat

legbabella

$26.94

Kentucky Derby 2026 - The Run for the Roses at Churchill Downs Bucket Hat

legbabella

$26.94

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Churchill Hats

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