Hats | Stay Winning

Crafted from quality materials with bold style, our hats enhance the looks of any casual outfit. This Stay Winning collection includes fashion essentials like dad hats, snapbacks, bandanas, and beanies.
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Stay Winning x Supdawk Cream Snapback Hat Stay Winning x Supdawk Cream Snapback Hat Quick View

Stay Winning x Supdawk Cream Snapback Hat

$ 44.99

Quantity
Stay Winning x Supdawk 5 panel Curved bill Premium wool  Fully embroidered
Stay Winning Cork Popper Gang Snapback Hat Stay Winning Cork Popper Gang Snapback Hat Quick View

Stay Winning Cork Popper Gang Snapback Hat

$ 44.99

Quantity
5-panel snapback Mesh back panels Wool front panels Fully embroidered w/ chenille
Stay Winning SW Black Snapback Hat Stay Winning SW Black Snapback Hat Quick View

Stay Winning SW Black Snapback Hat

$ 44.99

BLACK
Quantity
6 panel wool snap back Puff embroidery Black strap 
Stay Winning Black Snapback Hat Stay Winning Black Snapback Hat Quick View

Stay Winning Black Snapback Hat

$ 44.99

BLACK
Quantity
6 panel wool snap back Puff embroidery Black strap 
Stay Winning x Loudy Bo Snapback Hat Stay Winning x Loudy Bo Snapback Hat Quick View

Stay Winning x Loudy Bo Snapback Hat

$ 44.99

SIZE
COLOR
BLACK
Quantity
Stay Winning x Loudy Bo 5-panel snap back Mesh back panels Wool front panels Fully embroidered Yellow back strap
Stay Winning x Wrldclo Snapback Hat Stay Winning x Wrldclo Snapback Hat Quick View

Stay Winning x Wrldclo Snapback Hat

$ 44.99

SIZE
COLOR
BLACK
Quantity
Stay Winning x Wrldclo Black strap Curved bill Premium wool  Fully embroidered
Stay Winning Kasino Trucker Hat Stay Winning Kasino Trucker Hat Quick View

Stay Winning Kasino Trucker Hat

$ 24.99

SIZE
COLOR
BLACK
Quantity
Embroidered Last Kickz hat ever (Stay Winning x Kickz) White back strap Foam / Mesh Trucker
Stay Winning Carty The Frog Trucker Hat Stay Winning Carty The Frog Trucker Hat Quick View

Stay Winning Carty The Frog Trucker Hat

$ 44.99

Royal Blue
Quantity
5 panel Chenille/Embrodery Adjustable snapback Foam/Mesh Trucker Hat
Stay Winning Corduroy Bay Area Winners Hat (Green) Stay Winning Corduroy Bay Area Winners Hat (Green) Quick View

Stay Winning Corduroy Bay Area Winners Hat (Green)

$ 44.99

SIZE
COLOR
GREEN
Quantity
5 panel Corduroy curved bill Fully embroidered Gold snapback strap
Stay Winning A Million Ain't Enough Snapback Hat Stay Winning A Million Ain't Enough Snapback Hat Quick View

Stay Winning A Million Ain't Enough Snapback Hat

$ 44.99

SIZE
COLOR
BLACK
Quantity
6 panel wool snap back Puff embroidery Chenille SW Black strap 
Stay Winning Corduroy Red Hat Stay Winning Corduroy Red Hat Quick View

Stay Winning Corduroy Red Hat

$ 44.99

COLOR
RED
SIZE
Quantity
5 panel Corduroy curved bill Fully embroidered Red snapback strap.
Stay Winning Corduroy Navy Hat Stay Winning Corduroy Navy Hat Quick View

Stay Winning Corduroy Navy Hat

$ 44.99

SIZE
COLOR
BLUE
Quantity
5 panel Corduroy curved bill. Fully embroidered. Grey snapback strap.
Stay Winning Corduroy Northern Cali Winners Hat (GREEN) Stay Winning Corduroy Northern Cali Winners Hat (GREEN) Quick View

Stay Winning Corduroy Northern Cali Winners Hat (GREEN)

$ 44.99

SIZE
COLOR
GREEN
Quantity
5 panel Corduroy curved bill. Fully embroidered. Pink snapback strap.
Stay Winning Corduroy Bay Area Winners Hat (Yellow) Stay Winning Corduroy Bay Area Winners Hat (Yellow) Quick View

Stay Winning Corduroy Bay Area Winners Hat (Yellow)

$ 44.99

SIZE
COLOR
YELLOW
Quantity
5 panel Corduroy curved bill. Fully embroidered. Blue snapback strap.
Stay Winning Corduroy Black Hat Stay Winning Corduroy Black Hat Quick View

Stay Winning Corduroy Black Hat

$ 44.99

SIZE
COLOR
BLACK
Quantity
5 panel Corduroy curved bill. Fully embroidered. Black snapback strap.
Stay Winning East Bay Hyphy Hat Stay Winning East Bay Hyphy Hat Quick View

Stay Winning East Bay Hyphy Hat

$ 44.99

SIZE
COLOR
BLACK
Quantity
5 panel 2-tone corduroy curved bill. Fully embroidered. Purple snapback strap.
Stay Winning Hippie Scarf (Orange) Stay Winning Hippie Scarf (Orange) Quick View

Stay Winning Hippie Scarf (Orange)

$ 29.99

SIZE
COLOR
ORANGE
Quantity
75% Cotton 25% Silk 37" x 37” Dry clean only
Stay Winning Hippie Scarf (Mint) Stay Winning Hippie Scarf (Mint) Quick View

Stay Winning Hippie Scarf (Mint)

$ 29.99

SIZE
COLOR
BLUE
Quantity
75% Cotton 25% Silk 37" x 37" Dry clean only
Stay Winning Hippie Scarf (Yellow) Stay Winning Hippie Scarf (Yellow) Quick View

Stay Winning Hippie Scarf (Yellow)

$ 29.99

SIZE
COLOR
YELLOW
Quantity
75% Cotton 25% Silk 37" x 37” Dry clean only
Stay Winning Hippie Scarf (Pink) Stay Winning Hippie Scarf (Pink) Quick View

Stay Winning Hippie Scarf (Pink)

$ 29.99

SIZE
COLOR
PINK
Quantity
75% Cotton 25% Silk 37" x 37" Dry clean only
Stay Winning Travel Scarf (Green) Stay Winning Travel Scarf (Green) Quick View

Stay Winning Travel Scarf (Green)

$ 29.99

SIZE
COLOR
GREEN
Quantity
90% Wool 10% Silk 40"x 40" Dry clean only
Stay Winning Travel Scarf (White) Stay Winning Travel Scarf (White) Quick View

Stay Winning Travel Scarf (White)

$ 29.99

SIZE
COLOR
WHITE
Quantity
90% Wool 10% Silk 40"x 40" Dry clean only
Stay Winning Travel Scarf (Burgundy) Stay Winning Travel Scarf (Burgundy) Quick View

Stay Winning Travel Scarf (Burgundy)

$ 29.99

SIZE
COLOR
BURGUNDY
Quantity
90% Wool 10% Silk 40"x 40" Dry clean only
Stay Winning Travel Scarf (Navy) Stay Winning Travel Scarf (Navy) Quick View

Stay Winning Travel Scarf (Navy)

$ 29.99

SIZE
COLOR
BLUE
Quantity
90% Wool 10% Silk 40"x 40" Dry clean only
Stay Winning Bubbas Pre 98 Hat Stay Winning Bubbas Pre 98 Hat Quick View

Stay Winning Bubbas Pre 98 Hat

$ 44.99

SIZE
COLOR
BLACK
Quantity
5 panel 2-tone corduroy curved bill Embroidered Bubbas, 1998, trophy & Stay Winning Chenille patch lucky cat & East Bay SW White snapback ...
Stay Winning Red Trucker Hat Stay Winning Red Trucker Hat Quick View

Stay Winning Red Trucker Hat

$ 39.99

SIZE
COLOR
RED
Quantity
5 Panel Adjustable Foam trucker hat
Stay Winning Royal Blue Trucker Hat Stay Winning Royal Blue Trucker Hat Quick View

Stay Winning Royal Blue Trucker Hat

$ 39.99

SIZE
COLOR
BLUE
Quantity
5 Panel Adjustable Foam trucker hat
Stay Winning Navy Blue Trucker Hat Stay Winning Navy Blue Trucker Hat Quick View

Stay Winning Navy Blue Trucker Hat

$ 39.99

SIZE
COLOR
BLUE
Quantity
5 Panel Adjustable Foam trucker hat
Stay Winning Fortune Frogs Blue Trucker Hat Stay Winning Fortune Frogs Blue Trucker Hat Quick View

Stay Winning Fortune Frogs Blue Trucker Hat

$ 39.99

SIZE
COLOR
BLUE
Quantity
Embroidered Limited edition Classic trucker cap with premium mesh panels Hard buckram. Structured Matching plastic snapback closure
Stay Winning Fortune Frogs Red Trucker Hat Stay Winning Fortune Frogs Red Trucker Hat Quick View

Stay Winning Fortune Frogs Red Trucker Hat

$ 39.99

SIZE
COLOR
RED
Quantity
Embroidered Limited edition Classic trucker cap with premium mesh panels Hard buckram. Structured Matching plastic snapback closure
Stay Winning Fortune Frogs Green Beanie Quick View

Stay Winning Fortune Frogs Green Beanie

$ 39.99

SIZE
COLOR
GREEN
Quantity
Embroidered Limited edition Wide, ribbed knit Fitted, fisherman style, cuffed hem Mid weight 100% acrylic One size fits all
Sale
Stay Winning Green/White Dad Hat Stay Winning Green/White Dad Hat Quick View

Stay Winning Green/White Dad Hat

$ 19.99 $ 29.99

SIZE
COLOR
GREEN
Quantity
100% cotton, heavy brushed twill  Unstructured, low-profile, six-panel Pre-curved visor Tri-glide buckle closure

Stay Winning Green/White Dad Hat

$ 19.99
$ 29.99
Sale
Stay Winning Bubbas Maroon Snapback Hat Stay Winning Bubbas Maroon Snapback Hat Quick View

Stay Winning Bubbas Maroon Snapback Hat

$ 29.99 $ 39.99

SIZE
COLOR
MAROON
Quantity
Comes with an exclusive Bubbas & Gold Pin 80% Acrylic / 20% Wool (60% Cotton / 40% Polyester) Classic shape Premium wool blend Matching plast...
Sale
Stay Winning Bubbas Navy Blue Snapback Hat Stay Winning Bubbas Navy Blue Snapback Hat Quick View

Stay Winning Bubbas Navy Blue Snapback Hat

$ 29.99 $ 39.99

SIZE
COLOR
BLUE
Quantity
Comes with an exclusive Bubbas & Gold Pin 80% Acrylic / 20% Wool (60% Cotton / 40% Polyester) Classic shape Premium wool blend Matching plast...
Sale
Stay Winning Bubbas White Snapback Hat Stay Winning Bubbas White Snapback Hat Quick View

Stay Winning Bubbas White Snapback Hat

$ 29.99 $ 39.99

SIZE
COLOR
WHITE
Quantity
Comes with an exclusive Gold Pin 80% Acrylic / 20% Wool (60% Cotton / 40% Polyester) Classic shape Premium wool blend Matching plastic snap Class...
Sale
Stay Winning Bubbas Red Snapback Hat Stay Winning Bubbas Red Snapback Hat Quick View

Stay Winning Bubbas Red Snapback Hat

$ 29.99 $ 39.99

SIZE
COLOR
RED
Quantity
Comes with an exclusive Gold Pin 80% Acrylic / 20% Wool (60% Cotton / 40% Polyester) Classic shape Premium wool blend Matching plastic snap Class...
Sale
Stay Winning Bubbas Black Snapback Hat Stay Winning Bubbas Black Snapback Hat Quick View

Stay Winning Bubbas Black Snapback Hat

$ 29.99 $ 39.99

SIZE
COLOR
BLACK
Quantity
Comes with an exclusive Bubbas & Gold Pin 80% Acrylic / 20% Wool (60% Cotton / 40% Polyester) Classic shape Premium wool blend Matching plast...
Sale
Stay Winning SW Royal Blue/White Snapback Hat Stay Winning SW Royal Blue/White Snapback Hat Quick View

Stay Winning SW Royal Blue/White Snapback Hat

$ 29.99 $ 39.99

SIZE
COLOR
BLUE
Quantity
Comes with an exclusive SW Pin 80% Acrylic / 20% Wool (60% Cotton / 40% Polyester) Classic shape Premium wool blend Matching plastic snap Classic...
Sale
Stay Winning SW Maroon/White Snapback Hat Stay Winning SW Maroon/White Snapback Hat Quick View

Stay Winning SW Maroon/White Snapback Hat

$ 29.99 $ 39.99

SIZE
COLOR
MAROON
Quantity
Comes with an exclusive Gold Pin 80% Acrylic / 20% Wool (60% Cotton / 40% Polyester) Classic shape Premium wool blend Matching plastic snap Class...
Sale
Stay Winning SW Black/Aqua Snapback Hat Stay Winning SW Black/Aqua Snapback Hat Quick View

Stay Winning SW Black/Aqua Snapback Hat

$ 29.99 $ 39.99

SIZE
COLOR
BLACK
Quantity
Comes with an exclusive Gold Pin 80% Acrylic / 20% Wool (60% Cotton / 40% Polyester) Classic shape Premium wool blend Matching plastic snap Class...
Sale
Stay Winning Maroon/White Dad Hat Stay Winning Maroon/White Dad Hat Quick View

Stay Winning Maroon/White Dad Hat

$ 19.99 $ 29.99

SIZE
COLOR
MAROON
Quantity
100% cotton, heavy brushed twill  Unstructured, low-profile, six-panel Pre-curved visor Tri-glide buckle closure
Sale
Stay Winning Grey/White Dad Hat Quick View

Stay Winning Grey/White Dad Hat

$ 19.99 $ 29.99

SIZE
COLOR
GREY
Quantity
100% cotton, heavy brushed twill  Unstructured, low-profile, six-panel Pre-curved visor Tri-glide buckle closure
Sale
Stay Winning Pink/White Dad Hat Quick View

Stay Winning Pink/White Dad Hat

$ 19.99 $ 29.99

SIZE
COLOR
PINK
Quantity
100% cotton, heavy brushed twill  Unstructured, low-profile, six-panel Pre-curved visor Tri-glide buckle closure
Sale
Stay Winning Royal Blue/White Dad Hat Stay Winning Royal Blue/White Dad Hat Quick View

Stay Winning Royal Blue/White Dad Hat

$ 19.99 $ 29.99

SIZE
COLOR
BLUE
Quantity
100% cotton, heavy brushed twill  Unstructured, low-profile, six-panel Pre-curved visor Tri-glide buckle closure
Sale
Stay Winning Navy Blue/White Dad Hat Stay Winning Navy Blue/White Dad Hat Quick View

Stay Winning Navy Blue/White Dad Hat

$ 19.99 $ 29.99

SIZE
COLOR
BLUE
Quantity
100% cotton, heavy brushed twill  Unstructured, low-profile, six-panel Pre-curved visor Tri-glide buckle closure
Sale
Stay Winning Red/White Dad Hat Stay Winning Red/White Dad Hat Quick View

Stay Winning Red/White Dad Hat

$ 19.99 $ 29.99

SIZE
COLOR
RED
Quantity
100% cotton, heavy brushed twill  Unstructured, low-profile, six-panel Pre-curved visor Tri-glide buckle closure
Sale
Stay Winning Black/White Dad Hat Stay Winning Black/White Dad Hat Quick View

Stay Winning Black/White Dad Hat

$ 19.99 $ 29.99

SIZE
COLOR
BLACK
Quantity
100% cotton, heavy brushed twill  Unstructured, low-profile, six-panel Pre-curved visor Tri-glide buckle closure