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
Quick View
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
Quick View
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
Quick View
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
Quick View
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...
Quick View
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...
Quick View
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...
Quick View
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...
Quick View
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...
Quick View
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...
Quick View
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...
Quick View
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...
Quick View
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...
Sale
Quick View
Stay Winning SW Grey/Red Joggers
$ 29.99 $ 64.99
8.5 oz Soft-washed Fleece 100% cotton
Side slash pockets and back right pocket
Crotch gusset for ultimate comfort and style
Rib-knit ankle cuffs...
Sale
Quick View
Stay Winning Never Losing Grey/Red Hoodie
$ 29.99 $ 79.99
8.5 oz Soft-Washed 100% Cotton
Flat draw cords
3 panel hood for fashion and comfort
Puff print
*Model is 6' 165 lbs wearing a size M.*
Sale
Quick View
Stay Winning SW Grey/Blue Joggers
$ 29.99 $ 64.99
8.5 oz Soft-washed Fleece 100% cotton
Side slash pockets and back right pocket
Crotch gusset for ultimate comfort and style
Rib-knit ankle cuffs...
Sale
Quick View
Stay Winning Never Losing Grey/Blue Hoodie
$ 29.99 $ 79.99
8.5 oz Soft-Washed 100% Cotton
Flat draw cords
3 panel hood for fashion and comfort
Puff print
*Model is 6' 165 lbs wearing a size M.*
Sale
Quick View
Stay Winning SW Red/White Joggers
$ 29.99 $ 64.99
8.5 oz Soft-washed Fleece 100% cotton
Side slash pockets and back right pocket
Crotch gusset for ultimate comfort and style
Rib-knit ankle cuffs...
Sale
Quick View
Stay Winning Never Losing Red/White Hoodie
$ 29.99 $ 64.99
8.5 oz Soft-Washed 100% Cotton
Flat draw cords
3 panel hood for fashion and comfort
Puff print
*Model is 6' 165 lbs wearing a size M.*
Sale
Quick View
Stay Winning SW Royal Blue/White Joggers
$ 29.99 $ 64.99
8.5 oz Soft-washed Fleece 100% cotton
Side slash pockets and back right pocket
Crotch gusset for ultimate comfort and style
Rib-knit ankle cuffs...
Sale
Quick View
Stay Winning Never Losing Royal Blue/White Zip-Up Hoodie
$ 29.99 $ 64.99
8.5 oz Soft-Washed 100% Cotton
Flat draw cords
3 panel hood for fashion and comfort
Puff print
*Model is 6' 165 lbs wearing a size M.*
Sale
Quick View
Stay Winning Distressed Light Denim Jean Jacket
$ 64.99 $ 99.99
Navy Hoodie
4 outer pockets
1 inner pocket
Button up
100% cotton
*Model is 6' 150 lbs wearing a medium*
Sale
Quick View
Stay Winning Westside Neon White Zip-Up Hoodie
$ 29.99 $ 64.99
8.5 oz, soft washed
80% Cotton 20% Polyester
3-End Yarn
Silver Metal Zipper w/"scuba" hood
*Model is 6' 150 lbs wearing a medium*
Sale
Quick View
Stay Winning Script White/Pink Joggers
$ 29.99 $ 59.99
8.5 oz Soft-washed 80/20 Cotton Poly Fleece
Side slash pockets and back right pocket
Crotch gusset for ultimate comfort and style
Rib-knit ankle c...
Sale
Quick View
Stay Winning Mobb Meeting Grey Joggers
$ 29.99 $ 59.99
8.5 oz Soft-washed 80/20 Cotton Poly Fleece
Side slash pockets and back right pocket
Crotch gusset for ultimate comfort and style
Rib-knit ankle c...
Sale
Quick View
Stay Winning Mobb Meeting Grey Zip-Up Hoodie
$ 29.99 $ 79.99
8.5 oz, soft washed
80% Cotton 20% Polyester
3-End Yarn
Silver Metal Zipper w/"scuba" hood
*Model is 6' 150 lbs wearing a medium*
Sale
Quick View
Stay Winning Grey Banger Hoodie
$ 29.99 $ 64.99
Premium quality unisex hoodie
8.5 oz., 3-end fleece, soft-washed
100% cotton face. 65% cotton/35% polyester
Ultra-soft hand
Side-seamed
Tightly kn...
Sale
Quick View
Stay Winning Lucky Cat Black Hoodie
$ 29.99 $ 79.99
Regular Fit
Pullover hood, inset sleeves, kangaroo pocket
80% cotton 20% polyester anti-pill fleece
Lined hood, tonal shoestring drawcord, sleeve ...
Sale
Quick View
Stay Winning Red Bubbas Hoodie
$ 29.99 $ 64.99
65% Ringspun Cotton 35% Polyester
Flat draw cords
3 panel hood for fashion and comfort
Sale
Quick View
Stay Winning Black Bubbas Hoodie
$ 29.99 $ 64.99
Regular Fit
Pullover hood, inset sleeves, kangaroo pocket
80% cotton 20% polyester anti-pill fleece
Lined hood, tonal shoestring drawcord, sleeve ...
Sale
Quick View
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
Quick View
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
Quick View
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
Quick View
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
Quick View
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
Sale
Quick View
Stay Winning Blue 3M Windbreaker Zip-Up Jacket
$ 79.99 $ 99.99
3M REFLECTIVE
WATER PROOF
100% POLYESTER
MULTIPLE DRAWSTRINGS
6 LOGOS
GO UP 1 SIZE FOR A LOOSE BAGGY FIT.
(Model is 5'6" 165 lbs wearing a medium.)
Sale
Quick View
Stay Winning Red 3M Windbreaker Zip-Up Jacket
$ 79.99 $ 99.99
3M REFLECTIVE
WATER PROOF
100% POLYESTER
MULTIPLE DRAWSTRINGS
6 LOGOS
GO UP 1 SIZE FOR A LOOSE BAGGY FIT.
(Model is 5'6" 165 lbs wearing a medium.)
Sale
Quick View
Stay Winning Grey 3M Windbreaker Zip-Up Jacket
$ 79.99 $ 99.99
3M REFLECTIVE
WATER PROOF
100% POLYESTER
MULTIPLE DRAWSTRINGS
6 LOGOS
GO UP 1 SIZE FOR A LOOSE BAGGY FIT.
(Model is 5'6" 165 lbs wearing a medium.)
Sale
Quick View
Stay Winning Split Camo Chenille Hoodie
$ 29.99 $ 59.99
Chenille patch
Print on hood
100% Cotton
Side vent
Sale
Quick View
Stay Winning x Double Up DBZ/PIF Black Hoodie
$ 59.99 $ 79.99
Stay Winning x Double Up DBZ/PIF Black Hoodie
Super exclusive release w/ Double Up x Stay Winning
Regular fit
80% cotton 20% polyester anti-pill...
Quick View
Stay Winning x Double Up DBZ/PIF White Tee
$ 39.99
Stay Winning x Double Up DBZ/PIF White Tee
Super exclusive release w/ Double Up x Stay Winning
Regular Fit
Crew neck
100% combed cotton
Neck rib...
Quick View
Stay Winning x Double Up DBZ/PIF Black Tee
$ 39.99
Stay Winning x Double Up DBZ/PIF Black Tee
Super exclusive release w/ Double Up x Stay Winning
Regular Fit
Crew neck
100% combed cotton
Neck rib...
Sale
Quick View
Stay Winning Westside Neon Black Hoodie
$ 29.99 $ 64.99
Premium quality unisex hoodie
8.5 oz., 3-end fleece, soft-washed
100% cotton face. 65% cotton/35% polyester
Ultra-soft hand
Side-seamed
Tightly kn...
Sale
Quick View
Stay Winning Script Navy/Yellow Joggers
$ 29.99 $ 59.99
8.5 oz Soft-washed 80/20 Cotton Poly Fleece
Side slash pockets and back right pocket
Crotch gusset for ultimate comfort and style
Rib-knit a...
Sale
Quick View
Stay Winning OG/Script Logo Navy/Yellow Full Zip-Up Hoodie
$ 29.99 $ 64.99
8.5 oz, soft washed
80% Cotton 20% Polyester
3-End Yarn
Silver Metal Zipper w/"scuba" hood
Sale
Quick View
Stay Winning Script Navy/Red Joggers
$ 29.99 $ 59.99
8.5 oz Soft-washed 80/20 Cotton Poly Fleece
Side slash pockets and back right pocket
Crotch gusset for ultimate comfort and style
Rib-knit a...
Sale
Quick View
Stay Winning OG/Script Logo Navy/Red Full Zip-Up Hoodie
$ 29.99 $ 64.99
8.5 oz, soft washed
80% Cotton 20% Polyester
3-End Yarn
Silver Metal Zipper w/"scuba" hood
Sale
Quick View
Stay Winning Script Black/Neon Yellow Joggers
$ 29.99 $ 59.99
8.5 oz Soft-washed 80/20 Cotton Poly Fleece
Side slash pockets and back right pocket
Crotch gusset for ultimate comfort and style
Rib-knit a...
Sale
Quick View
Stay Winning OG/Script Logo Black/Neon Yellow Full Zip-Up Hoodie
$ 29.99 $ 64.99
8.5 oz, soft washed
80% Cotton 20% Polyester
3-End Yarn
Silver Metal Zipper w/"scuba" hood
Connect