Sissies Caps

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735 items

Retro Horror Movie Dad Hat

ZEtexaxe

$23.09

Portrait of the empress Sissy Baseball Cap

HenrikssonFrej

$23.09

Gen X The Badass Generation Before All You Sissies Were Born Generation X Pride Vintage Humor Baseball Cap

JonesFlora2025

$33.58

Gen X The Badass Generation Before All You Sissies Were Born Generation X Pride Baseball Cap

SkeletonsDanger

$33.58

Gen X The Badass Generation Before All You Sissies Were Born Generational Humor Gen X Pride Baseball Cap

JonesFlora2025

$33.58

My Foreman Cross Dresser Baseball Cap

DonovanEllis

$25.19

Africa Is Not For Sissies Dad Hat

YasmeThiel

$25.19

Gen X Before All You Sissies Were Born Generation X Funny Adult Sarcastic Dad Hat

JonesFlora2025

$33.58

Me And The Boys Femboy Maids Dad Hat

ClaireCum

$25.19

Just One More Dress Baseball Cap

ClaireCum

$25.19

Crossdressing Don’t Disturb Me Baseball Cap

ClaireCum

$25.19

Sissy Maid Anime Baseball Cap

ClaireCum

$25.19

Sissy Pastel Hearts Baseball Cap

ClaireCum

$25.19

Cute Little Femboy Dad Hat

ClaireCum

$25.19

Femboy Friday Maid Baseball Cap

ClaireCum

$25.19

Item preview, Gen X The Badass Generation Before All You Sissies Were Born Motorcycle Rider Generational Pride designed and sold by JonesFlora2025.

Gen X The Badass Generation Before All You Sissies Were Born Motorcycle Rider Generational Pride Baseball Cap

JonesFlora2025

$33.58

Gen X The Badass Generation Before All You Sissies Were Born Generation X Pride Dad Hat

RetroMini2026

$33.58

Terror Movie Fan Retro Style Dad Hat

JASOARMAN

$25.19

Generation X The Badass Generation Before All Of You Sissies Were Born Gen X Dad Hat

SkeletonsDanger

$33.58

Gen X The Badass Generation Before All You Sissies Were Born GenX Adult Humor Dad Hat

Simsimah26Parks

$41.98

Gen X The Badass Generation Before All You Sissies Were Born Generational Pride Gen X Humor Dad Hat

JonesFlora2025

$33.58

Gen X Before All You Sissies Were Born Generation X Funny Humorous Xer Sarcastic Dad Hat

JonesFlora2025

$33.58

Sissy Maid Covert - Finishing School Dad Hat

Laymela Underground

$25.19

Old Age — Turns Out I’m a Sissy Dad Hat

purrtees

$25.19

The Badass Generation Before All You Sissies were Born Baseball Cap

KodiakMillyy

$27.50

Gen X Before All You Sissies Were Born Generation X Proud Gen Xer Attitude Dad Hat

RetroMini2026

$33.58

Gen X The Badass Generation Before All You Sissies Were Born Generational Pride Baseball Cap

HumansStuck12

$31.49

Gen X The Badass Generation Before All You Sissies Were Born Generation X Humor Dad Hat

HumansStuck12

$31.49

Gen X Before All You Sissies Were Born Generation X Sarcastic Pride Baseball Cap

HumansStuck12

$31.49

Gen X The Badass Generation Before All You Sissies Were Born Generation X Attitude Baseball Cap

HumansStuck12

$31.49

Introvert but willing to discuss Carrie Baseball Cap

Stylish Hubby Lettering in Pink and Black Baseball Cap

Between-Words

$23.09

Stylish Hubby Lettering in Pink and Black Baseball Cap

Between-Words

$23.09

Ethnocentric Femboy RG with flag Dad Hat

Devox-

$23.09

A Reckless Run Across the Plains – Badlands Fine Art Print Baseball Cap

Art's Diner

$23.09

Bud and Sissy Gilley’s Texas | Urban Cowboy Movie 4th of July Dad Hat

Harmontal

$26.24

Sissy - as worn by Stone Gossard of Pearl Jam Baseball Cap

rockthatshirt

$23.09

Vintage Lookin' for Love in All the Wrong Places Country Romance Patriotic Dad Hat

Regainbara

$26.24

Stay Locked for HOA Baseball Cap

LadyAnacondaHoa

$25.19

Earth Football Is For Sissies Dad Hat

Patricia Brown

$23.09

GENDER EUPHORIA FEMBOY Baseball Cap

remerasnerdas

$25.19

Boomers The Badass Generation Before All You Sissies Were Born Dad Hat

CCChillingfrog

$24.35

If Only They Knew She Power Carrie Art Dad Hat

y2kponyclub

$23.09

Carrie White Prom Queen Horror Aesthetic Baseball Cap

y2kponyclub

$23.09

Carrie White Female Trouble Horror Aesthetic Dad Hat

y2kponyclub

$23.09

Softball Sister My Sissy Is On That Field Baseball Cap

KroghDs

$25.82

My Sissy Is On That Field Softball Sister Baseball Cap

KroghDs

$25.82

Softball Sister My Sissy Is On That Field Baseball Cap

KroghDs

$25.82

Proud Softball Sister My Sissy Is On That Field Dad Hat

KroghDs

$25.19

Softball Sister My Sissy Is On That Field Dad Hat

KroghDs

$25.19

Softball Sister My Sissy Is On That Field Baseball Cap

KroghDs

$25.82

My Sissy Is On That Field Softball Sister Dad Hat

KroghDs

$25.19

Softball Sister My Sissy Is On That Field Baseball Cap

KroghDs

$25.82

Softball Sister My Sissy Is On That Field Dad Hat

KroghDs

$25.19

Softball Sister My Sissy Is On That Field Baseball Cap

KroghDs

$25.82

Softball Sister My Sissy Is On That Field Baseball Cap

KroghDs

$25.82

Softball Sister My Sissy Is On That Field Baseball Cap

KroghDs

$25.82

Proud Softball Sister My Sissy Is On That Field Dad Hat

KroghDs

$25.19

Softball Sister My Sissy Is On That Field Baseball Cap

KroghDs

$25.82

Softball Sister My Sissy Is On That Field Baseball Cap

KroghDs

$25.82

Softball Sister Sissy Sports Game Day Baseball Cap

KroghDs

$25.82

Softball Sister My Sissy Is On That Field Dad Hat

KroghDs

$25.19

Softball Sister My Sissy Is On That Field Baseball Cap

KroghDs

$25.82

Sissy Princess Baseball Cap

XKaleidoscopeX

$23.09

Size Queen Baseball Cap

XKaleidoscopeX

$23.09

Boomer Generation Badass Before All You Sissies 1946-1964 Baseball Cap

Inglisue

$25.19

My Sissy Is On That Field Funny Softball Sister Game Day Family Design Dad Hat

kiralynstration

$27.29

My Sissy Is On That Field Funny Softball Sister Game Day Sports Family Dad Hat

Red Heel Sissy Baseball Cap

X Generation Before All You Sissies Were Born Dad Hat

Millsoft

$25.19

X Generation Before All You Sissies Were Born Dad Hat

Millsoft

$25.19

X Generation Before All You Sissies Were Born Dad Hat

Millsoft

$25.19

Big Sis White Heart Wavy Typography Dad Hat

WAMTEES

$25.19

Big Sis Black Heart Wavy Typography Dad Hat

WAMTEES

$25.19

My Sissy Is On That Field Softball Sister Baseball Cap

The Straight Story 1999 Dad Hat

MORKINO POSTERS

$26.24

NO SISSY GIRL Baseball Cap

Jen Whitaker

$25.19

My Favorite Volleyball Player Calls Me Sissy USA Flag Dad Hat

FadeOfThrone

$25.19

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Sissies Caps

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