Stay Winning Hats

  • Sort by

  • Shop by Color

  • Shop by Material

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
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
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 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 Black Trucker Hat Stay Winning Black Trucker Hat Quick View

Stay Winning Black Trucker Hat

$ 39.99

SIZE
COLOR
BLACK
Quantity
5 Panel Adjustable Foam trucker hat
Stay Winning SW Grey/Black Snap Back Hat Stay Winning SW Grey/Black Snap Back Hat Quick View

Stay Winning SW Grey/Black Snap Back Hat

$ 39.99

SIZE
COLOR
GREY
Quantity
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 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 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
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 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 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
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 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 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
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
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
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
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
Stay Winning SW Royal Blue/White Snap Back Hat Stay Winning SW Royal Blue/White Snap Back Hat Quick View

Stay Winning SW Royal Blue/White Snap Back Hat

$ 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 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
Stay Winning Bubbas Black Snap Back Hat Stay Winning Bubbas Black Snap Back Hat Quick View

Stay Winning Bubbas Black Snap Back Hat

$ 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...
Stay Winning SW Maroon/White Snap Back Hat Stay Winning SW Maroon/White Snap Back Hat Quick View

Stay Winning SW Maroon/White Snap Back Hat

$ 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...
Stay Winning Bubbas Red Snap Back Hat Stay Winning Bubbas Red Snap Back Hat Quick View

Stay Winning Bubbas Red Snap Back Hat

$ 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...
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 x Loudy Bo Snap Back Hat Stay Winning x Loudy Bo Snap Back Hat Quick View

Stay Winning x Loudy Bo Snap Back 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 Bubbas Maroon Snap Back Hat Stay Winning Bubbas Maroon Snap Back Hat Quick View

Stay Winning Bubbas Maroon Snap Back Hat

$ 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...
Stay Winning x Wrldclo Snap Back Hat Stay Winning x Wrldclo Snap Back Hat Quick View

Stay Winning x Wrldclo Snap Back 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 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 Black Trucker Hat Stay Winning Fortune Frogs Black Trucker Hat Quick View

Stay Winning Fortune Frogs Black Trucker Hat

$ 39.99

SIZE
COLOR
BLACK
Quantity
Embroidered Limited edition Classic trucker cap with premium mesh panels Hard buckram. Structured Matching plastic snapback closure
Stay Winning Bubbas Navy Blue Snap Back Hat Stay Winning Bubbas Navy Blue Snap Back Hat Quick View

Stay Winning Bubbas Navy Blue Snap Back Hat

$ 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...
Stay Winning Bubbas White Snap Back Hat Stay Winning Bubbas White Snap Back Hat Quick View

Stay Winning Bubbas White Snap Back Hat

$ 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...
Stay Winning SW Black/Aqua Snap Back Hat Stay Winning SW Black/Aqua Snap Back Hat Quick View

Stay Winning SW Black/Aqua Snap Back Hat

$ 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...