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.
Sort by
Featured
Price, low to high
Price, high to low
Alphabetically, A-Z
Alphabetically, Z-A
Date, old to new
Date, new to old
Best Selling
Shop by Color
All
BLACK
BLUE
GREEN
GRAY
MAROON
ORANGE
PINK
PURPLE
RED
WHITE
YELLOW
Shop by Material
All
ACCESSORIES
HATS
MENS
Stay Winning Carty The Frog Trucker Hat
$ 44.99
5 panel
Foam/Mesh Trucker Hat
Chenille/Embrodery
Adjustable snapback
Stay Winning Corduroy Bay Area Winners Hat (Green)
$ 44.99
5 panel
Corduroy curved bill
Fully embroidered
Gold snapback strap
Stay Winning A Million Ain't Enough Snap Back Hat
$ 44.99
6 panel
Puff embroidery
Chenille SW
Black strap
Stay Winning Corduroy Red Hat
$ 44.99
5 panel
Corduroy curved bill
Fully embroidered
Red snapback strap.
Stay Winning Corduroy Navy Hat
$ 44.99
5 panel
Corduroy curved bill.
Fully embroidered.
Grey snapback strap.
Stay Winning Corduroy Northern Cali Winners Hat (GREEN)
$ 44.99
5 panel
Corduroy curved bill.
Fully embroidered.
Pink snapback strap.
Stay Winning Corduroy Bay Area Winners Hat (Yellow)
$ 44.99
5 panel
Corduroy curved bill.
Fully embroidered.
Blue snapback strap.
Stay Winning Corduroy Black Hat
$ 44.99
5 panel
Corduroy curved bill.
Fully embroidered.
Black snapback strap.
Stay Winning East Bay Hyphy Hat
$ 44.99
5 panel
2-tone corduroy curved bill.
Fully embroidered.
Purple snapback strap.
Stay Winning Hippie Scarf (Orange)
$ 29.99
75% Cotton 25% Silk
37" x 37”
Stay Winning Hippie Scarf (Mint)
$ 29.99
75% Cotton 25% Silk
37" x 37"
Stay Winning Hippie Scarf (Yellow)
$ 29.99
75% Cotton 25% Silk
37" x 37”
Stay Winning Hippie Scarf (Pink)
$ 29.99
75% Cotton 25% Silk
37" x 37"
Stay Winning Travel Scarf (Green)
$ 29.99
90% Wool 10% Silk
40"x 40"
Stay Winning Travel Scarf (White)
$ 29.99
90% Wool 10% Silk
40"x 40"
Stay Winning Travel Scarf (Burgundy)
$ 29.99
90% Wool 10% Silk
40"x 40"
Stay Winning Travel Scarf (Navy)
$ 29.99
90% Wool 10% Silk
40"x 40"
Stay Winning Bubbas Pre 98 Hat
$ 44.99
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
$ 39.99
5 Panel
Adjustable
Foam trucker hat
Stay Winning Royal Blue Trucker Hat
$ 39.99
5 Panel
Adjustable
Foam trucker hat
Stay Winning Navy Blue Trucker Hat
$ 39.99
5 Panel
Adjustable
Foam trucker hat
Stay Winning Black Trucker Hat
$ 39.99
5 Panel
Adjustable
Foam trucker hat
Stay Winning Fortune Frogs Blue Trucker Hat
$ 39.99
Embroidered
Limited edition
Classic trucker cap with premium mesh panels
Hard buckram. Structured
Matching plastic snapback closure
Stay Winning Fortune Frogs Red Trucker Hat
$ 39.99
Embroidered
Limited edition
Classic trucker cap with premium mesh panels
Hard buckram. Structured
Matching plastic snapback closure
Stay Winning Fortune Frogs Black Trucker Hat
$ 39.99
Embroidered
Limited edition
Classic trucker cap with premium mesh panels
Hard buckram. Structured
Matching plastic snapback closure
Stay Winning Fortune Frogs Green Beanie
$ 39.99
Embroidered
Limited edition
Wide, ribbed knit
Fitted, fisherman style, cuffed hem
Mid weight
100% acrylic
One size fits all
Stay Winning Fortune Frogs Red Beanie
$ 39.99
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
$ 19.99 $ 29.99
100% cotton, heavy brushed twill
Unstructured, low-profile, six-panel
Pre-curved visor
Tri-glide buckle closure
Stay Winning Bubbas Maroon Snap Back Hat
$ 39.99
Comes with an exclusive Bubbas & Gold Pin
80% Acrylic / 20% Wool (60% Cotton / 40% Polyester)
Classic shape
Premium wool blend
Matching plast...
Stay Winning Bubbas Navy Blue Snap Back Hat
$ 39.99
Comes with an exclusive Bubbas & Gold Pin
80% Acrylic / 20% Wool (60% Cotton / 40% Polyester)
Classic shape
Premium wool blend
Matching plast...
Stay Winning Bubbas White Snap Back Hat
$ 39.99
Comes with an exclusive Gold Pin
80% Acrylic / 20% Wool (60% Cotton / 40% Polyester)
Classic shape
Premium wool blend
Matching plastic snap
Class...
Stay Winning Bubbas Red Snap Back Hat
$ 39.99
Comes with an exclusive Gold Pin
80% Acrylic / 20% Wool (60% Cotton / 40% Polyester)
Classic shape
Premium wool blend
Matching plastic snap
Class...
Stay Winning Bubbas Black Snap Back Hat
$ 39.99
Comes with an exclusive Bubbas & Gold Pin
80% Acrylic / 20% Wool (60% Cotton / 40% Polyester)
Classic shape
Premium wool blend
Matching plast...
Stay Winning SW Royal Blue/White Snap Back Hat
$ 39.99
Comes with an exclusive SW Pin
80% Acrylic / 20% Wool (60% Cotton / 40% Polyester)
Classic shape
Premium wool blend
Matching plastic snap
Classic...
Stay Winning SW Maroon/White Snap Back Hat
$ 39.99
Comes with an exclusive Gold Pin
80% Acrylic / 20% Wool (60% Cotton / 40% Polyester)
Classic shape
Premium wool blend
Matching plastic snap
Class...
Stay Winning SW Black/Aqua Snap Back Hat
$ 39.99
Comes with an exclusive Gold Pin
80% Acrylic / 20% Wool (60% Cotton / 40% Polyester)
Classic shape
Premium wool blend
Matching plastic snap
Class...
Stay Winning SW Grey/Black Snap Back Hat
$ 39.99
Comes with an exclusive Gold Pin
80% Acrylic / 20% Wool (60% Cotton / 40% Polyester)
Classic shape
Premium wool blend
Matching plastic snap
Class...
Sold Out
Stay Winning SW Black/White Snap Back Hat
Sold Out
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
$ 19.99 $ 29.99
100% cotton, heavy brushed twill
Unstructured, low-profile, six-panel
Pre-curved visor
Tri-glide buckle closure
Sale
Stay Winning Grey/White Dad Hat
$ 19.99 $ 29.99
100% cotton, heavy brushed twill
Unstructured, low-profile, six-panel
Pre-curved visor
Tri-glide buckle closure
Sale
Stay Winning Pink/White Dad Hat
$ 19.99 $ 29.99
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
$ 19.99 $ 29.99
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
$ 19.99 $ 29.99
100% cotton, heavy brushed twill
Unstructured, low-profile, six-panel
Pre-curved visor
Tri-glide buckle closure
Sold Out
Stay Winning Black Beanie
Sold Out
Black cuff beanie
100% Acrylic knit
Allover black fabrication
"STAY WINNING" embroidered on front
Sold Out
Stay Winning Red/White Snap Back Hat
Sold Out
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 Red/White Dad Hat
$ 19.99 $ 29.99
100% cotton, heavy brushed twill
Unstructured, low-profile, six-panel
Pre-curved visor
Tri-glide buckle closure
Sale
Stay Winning Black/White Dad Hat
$ 19.99 $ 29.99
100% cotton, heavy brushed twill
Unstructured, low-profile, six-panel
Pre-curved visor
Tri-glide buckle closure
Stay Winning Black/White Snap Back Hat
$ 39.99
Comes with an exclusive Gold Pin
80% Acrylic / 20% Wool (60% Cotton / 40% Polyester)
Classic shape
Premium wool blend
Matching plastic snap
Classi...
Connect