STAY WINNING
Stay Winning is a lifestyle mindset in a stylish manner. An all American classic street wear brand motivating the masses in apparel & accessory format. Encouraging you to fight the pursuit of living the American Dream on a daily basis. A strong powerful message so positive reminding you daily that you can make it through. Spreading this energy with a glow everywhere you go. Designed to make you feel proud & confident in your appearance. Originated in Northern California with a timeless universal reach that can relate to all walks of life. This is STAY WINNING.
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
GOLD
GREEN
GRAY
MAROON
ORANGE
PINK
PURPLE
RED
TEAL
WHITE
YELLOW
Shop by Material
All
ACCESSORIES
BACKPACK
BUTTON-UP
CREW NECK SWEATER
HATS
HOODED SWEATSHIRT
JACKETS
JOGGERS
KIDS
LONG SLEEVE
MENS
SHORTS
SLIDES
TEES
WOMENS
Stay Winning Hippie Scarf (Orange)
$ 29.99
75% Cotton 25% Silk
37" x 37”
Dry clean only
Stay Winning Hippie Scarf (Mint)
$ 29.99
75% Cotton 25% Silk
37" x 37"
Dry clean only
Stay Winning Hippie Scarf (Yellow)
$ 29.99
75% Cotton 25% Silk
37" x 37”
Dry clean only
Stay Winning Hippie Scarf (Pink)
$ 29.99
75% Cotton 25% Silk
37" x 37"
Dry clean only
Stay Winning Travel Scarf (Green)
$ 29.99
90% Wool 10% Silk
40"x 40"
Dry clean only
Stay Winning Travel Scarf (White)
$ 29.99
90% Wool 10% Silk
40"x 40"
Dry clean only
Stay Winning Travel Scarf (Burgundy)
$ 29.99
90% Wool 10% Silk
40"x 40"
Dry clean only
Stay Winning Travel Scarf (Navy)
$ 29.99
90% Wool 10% Silk
40"x 40"
Dry clean only
Stay Winning Americano Varsity Jacket
$ 299.99
Chenille
Embroidery
Inside pocket
Button down
24 oz genuine wool w/ smooth cow hide leather.
Go one size up for a better fit.
Limited quantity, hi...
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 Black Long Sleeve Pocket Tee
$ 44.99
Relaxed fit
Crew neck, tonal colour pocket
Heavy weight, 6.5 oz
100% combed cotton
Neck ribbing, side seamed, cuffed sleeves, shoulder to shoulder...
Stay Winning White Long Sleeve Pocket Tee
$ 44.99
Relaxed fit
Crew neck, tonal colour pocket
Heavy weight, 6.5 oz
100% combed cotton
Neck ribbing, side seamed, cuffed sleeves, shoulder to shoulder...
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
Sale
Stay Winning "Never Give Up" Plum Hoodie
$ 79.99 $ 89.99
Relaxed, oversized fit with dropped shoulders
Heavy weight, 11.8 oz
80% cotton 20% polyester
Go one size down for a better fit
Sale
Stay Winning "Never Give Up" Pine Green Hoodie
$ 79.99 $ 89.99
Relaxed, oversized fit with dropped shoulders
Heavy weight, 11.8 oz
80% cotton 20% polyester
Go one size down for a better fit
Stay Winning Pale Pink/Light Blue Crop Top Tee
$ 39.99
100% combed cotton
Relaxed fit
Crew neck
Mid weight, 5.3 oz
Short body, dropped shoulders, neck ribbing, side seamed, shoulder to shoulder tape, d...
Stay Winning Coal/Red Crop Top Tee
$ 39.99
100% combed cotton
Relaxed fit
Crew neck
Mid weight, 5.3 oz
Short body, dropped shoulders, neck ribbing, side seamed, shoulder to shoulder tape, d...
Stay Winning Sage/Icy Blue Crop Top Tee
$ 39.99
100% combed cotton
Relaxed fit
Crew neck
Mid weight, 5.3 oz
Short body, dropped shoulders, neck ribbing, side seamed, shoulder to shoulder tape, d...
Stay Winning Pistachio/Pink Crop Top Tee
$ 39.99
100% combed cotton
Relaxed fit
Crew neck
Mid weight, 5.3 oz
Short body, dropped shoulders, neck ribbing, side seamed, shoulder to shoulder tape, d...
Stay Winning Cream/Green Crop Top Tee
$ 39.99
100% combed cotton
Relaxed fit
Crew neck
Mid weight, 5.3 oz
Short body, dropped shoulders, neck ribbing, side seamed, shoulder to shoulder tape, d...
Stay Winning Berry/Black Crop Top Tee
$ 39.99
100% combed cotton
Relaxed fit
Crew neck
Mid weight, 5.3 oz
Short body, dropped shoulders, neck ribbing, side seamed, shoulder to shoulder tape,...
Stay Winning Camel/White Crop Top Tee
$ 39.99
Stay Winning Camel/White Crop Top Tee
100% combed cotton
Relaxed fit
Crew neck
Mid weight, 5.3 oz
Short body, dropped shoulders, neck ribbing, sid...
Stay Winning Mauve/Pink Crop Top Tee
$ 39.99
100% combed cotton
Relaxed fit
Crew neck
Mid weight, 5.3 oz
Short body, dropped shoulders, neck ribbing, side seamed, shoulder to shoulder tape, d...
Stay Winning Grey/Black Crop Top Tee
$ 39.99
100% combed cotton
Relaxed fit
Crew neck
Mid weight, 5.3 oz
Short body, dropped shoulders, neck ribbing, side seamed, shoulder to shoulder tape, d...
Stay Winning Red Backpack
$ 29.99
100% Polyester fabric
Waterproof
Front pockets
Side pockets
Length 16.5” Width 10.5” Depth 4”
Limited Edition
Stay Winning Blue Backpack
$ 29.99
100% Polyester fabric
Waterproof
Front pockets
Side pockets
Length 16.5” Width 10.5” Depth 4”
Limited Edition
Stay Winning Carty The Frog Backpack
$ 29.99
100% Polyester fabric
Waterproof
Front pockets
Side pockets
Length 16.5” Width 10.5” Depth 4”
Limited Edition
Stay Winning Red Bubbas Backpack
$ 29.99
100% Polyester fabric
Waterproof
Front pockets
Side pockets
Length 16.5” Width 10.5” Depth 4”
Limited Edition
Stay Winning Black Bubbas Backpack
$ 29.99
100% Polyester fabric
Waterproof
Front pockets
Side pockets
Length 16.5” Width 10.5” Depth 4”
Limited Edition
Stay Winning Americano Backpack
$ 29.99
100% Polyester fabric
Waterproof
Front pockets
Side pockets
Length 16.5” Width 10.5” Depth 4”
Limited Edition
Stay Winning Black Backpack
$ 29.99
100% Polyester fabric
Waterproof
Front pockets
Side pockets
Length 16.5” Width 10.5” Depth 4”
Limited Edition
Sale
Stay Winning Bubbas Bluetooth Speaker Glow Tray w/ Scale
$ 29.99 $ 44.99
USB powered glow tray
Bluetooth speakers on bottom
Built in digital scale 500 gram capacity (2 AAA battery operated)
Dust bag
Limited Edition
(pre...
Sale
Stay Winning Bluetooth Speaker Glow Tray w/ Scale
$ 29.99 $ 44.99
USB powered glow tray
Bluetooth speakers on bottom
Built in digital scale 500 gram capacity (2 AAA battery operated)
Dust bag
Limited Edition
(pre...
Sale
Stay Winning Black Money Gun
$ 19.99 $ 29.99
Limited Edition 60 per color
Battery operated (2 AA)
Comes in a box w/ prop money
When on low don't throw if you owe
Sale
Stay Winning Red Money Gun
$ 19.99 $ 29.99
Limited Edition 60 per color
Battery operated (2 AA)
Comes in a box w/ prop money
When on low don't throw if you owe
Sale
Stay Winning Blue Money Gun
$ 19.99 $ 29.99
Limited Edition 60 per color
Battery operated (2 AA)
Comes in a box w/ prop money
When on low don't throw if you owe
Sale
Stay Winning Gold Money Gun
$ 19.99 $ 29.99
Limited Edition 60 per color
Battery operated (2 AA)
Comes in a box w/ prop money
When on low don't throw if you owe
Sale
Crack Rock A Million Ain't Enough Digital Scale
$ 29.99 $ 39.99
Limited edition
1000 gram capacity
From the "A Million Ain't Enough" album by C-Roc
Battery operated
Stay Winning Fortune Frogs Grey Hoodie
$ 89.99
Embroidered
Limited edition NFT drop
80% cotton 20% polyester anti-pill fleece
Pullover hood, raglan sleeves, kangaroo pocket, lined hood, tonal d...
Stay Winning Fortune Frogs Yellow Hoodie
$ 89.99
Embroidered
Limited edition NFT drop
80% cotton 20% polyester anti-pill fleece
Pullover hood, raglan sleeves, kangaroo pocket, lined hood, tonal d...
Stay Winning Fortune Frogs Blue Hoodie
$ 89.99
Embroidered
Limited edition NFT drop
80% cotton 20% polyester anti-pill fleece
Pullover hood, raglan sleeves, kangaroo pocket, lined hood, tonal d...
Stay Winning Fortune Frogs Black Hoodie
$ 89.99
Embroidered
Limited edition NFT drop
80% cotton 20% polyester anti-pill fleece
Pullover hood, raglan sleeves, kangaroo pocket, lined hood, tonal d...
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
Connect