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

  • Shop by Color

  • Shop by Material

Sale
Stay Winning Bubbas Navy Blue Snapback Hat Stay Winning Bubbas Navy Blue Snapback Hat Quick View

Stay Winning Bubbas Navy Blue Snapback Hat

$ 30.00 $ 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

$ 30.00 $ 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

$ 30.00 $ 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

$ 30.00 $ 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 Maroon/White Snapback Hat Stay Winning SW Maroon/White Snapback Hat Quick View

Stay Winning SW Maroon/White Snapback Hat

$ 30.00 $ 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

$ 30.00 $ 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 SW Grey/Red Joggers Stay Winning SW Grey/Red Joggers Quick View

Stay Winning SW Grey/Red Joggers

$ 30.00 $ 64.99

SIZE
COLOR
GREY
Quantity
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...

Stay Winning SW Grey/Red Joggers

$ 30.00
$ 64.99
Sale
Stay Winning Never Losing Grey/Red Hoodie Stay Winning Never Losing Grey/Red Hoodie Quick View

Stay Winning Never Losing Grey/Red Hoodie

$ 30.00 $ 79.99

SIZE
COLOR
GREY
Quantity
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
Stay Winning SW Grey/Blue Joggers Stay Winning SW Grey/Blue Joggers Quick View

Stay Winning SW Grey/Blue Joggers

$ 30.00 $ 64.99

SIZE
COLOR
GREY
Quantity
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
Stay Winning Never Losing Grey/Blue Hoodie Stay Winning Never Losing Grey/Blue Hoodie Quick View

Stay Winning Never Losing Grey/Blue Hoodie

$ 30.00 $ 79.99

SIZE
COLOR
GREY
Quantity
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
Stay Winning SW Red/White Joggers Stay Winning SW Red/White Joggers Quick View

Stay Winning SW Red/White Joggers

$ 30.00 $ 64.99

SIZE
COLOR
RED
Quantity
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...

Stay Winning SW Red/White Joggers

$ 30.00
$ 64.99
Sale
Stay Winning SW Royal Blue/White Joggers Stay Winning SW Royal Blue/White Joggers Quick View

Stay Winning SW Royal Blue/White Joggers

$ 30.00 $ 64.99

SIZE
COLOR
BLUE
Quantity
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
Stay Winning Distressed Light Denim Jean Jacket Stay Winning Distressed Light Denim Jean Jacket Quick View

Stay Winning Distressed Light Denim Jean Jacket

$ 60.00 $ 99.99

SIZE
COLOR
WHITE
Quantity
Navy Hoodie 4 outer pockets 1 inner pocket Button up 100% cotton *Model is 6' 150 lbs wearing a medium*
Sale
Stay Winning Script White/Pink Joggers Stay Winning Script White/Pink Joggers Quick View

Stay Winning Script White/Pink Joggers

$ 30.00 $ 59.99

SIZE
COLOR
WHITE
Quantity
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
Stay Winning Mobb Meeting Grey Joggers Quick View

Stay Winning Mobb Meeting Grey Joggers

$ 30.00 $ 59.99

SIZE
COLOR
GREY
Quantity
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
Stay Winning Grey Banger Hoodie Stay Winning Grey Banger Hoodie Quick View

Stay Winning Grey Banger Hoodie

$ 30.00 $ 64.99

SIZE
COLOR
GREY
Quantity
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
Stay Winning Red Bubbas Hoodie Stay Winning Red Bubbas Hoodie Quick View

Stay Winning Red Bubbas Hoodie

$ 30.00 $ 64.99

SIZE
COLOR
RED
Quantity
65% Ringspun Cotton 35% Polyester Flat draw cords 3 panel hood for fashion and comfort
Sale
Stay Winning Black Bubbas Hoodie Stay Winning Black Bubbas Hoodie Quick View

Stay Winning Black Bubbas Hoodie

$ 30.00 $ 64.99

SIZE
COLOR
BLACK
Quantity
Regular Fit Pullover hood, inset sleeves, kangaroo pocket 80% cotton 20% polyester anti-pill fleece Lined hood, tonal shoestring drawcord, sleeve ...
Sale
Stay Winning Navy Blue/White Dad Hat Stay Winning Navy Blue/White Dad Hat Quick View

Stay Winning Navy Blue/White Dad Hat

$ 20.00 $ 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 Blue 3M Windbreaker Zip-Up Jacket Stay Winning Blue 3M Windbreaker Zip-Up Jacket Quick View

Stay Winning Blue 3M Windbreaker Zip-Up Jacket

$ 65.00 $ 99.99

SIZE
COLOR
BLUE
Quantity
3M REFLECTIVE WATER PROOF 100% POLYESTER MULTIPLE DRAWSTRINGS 6 LOGOS GO UP 1 SIZE FOR A BETTER FIT. (Model is 5'6" 165 lbs wearing a medium.)
Sale
Stay Winning Red 3M Windbreaker Zip-Up Jacket Stay Winning Red 3M Windbreaker Zip-Up Jacket Quick View

Stay Winning Red 3M Windbreaker Zip-Up Jacket

$ 65.00 $ 99.99

SIZE
COLOR
RED
Quantity
3M REFLECTIVE WATER PROOF 100% POLYESTER MULTIPLE DRAWSTRINGS 6 LOGOS GO UP 1 SIZE FOR A BETTER FIT. (Model is 5'6" 165 lbs wearing a medium.)
Sale
Stay Winning Grey 3M Windbreaker Zip-Up Jacket Stay Winning Grey 3M Windbreaker Zip-Up Jacket Quick View

Stay Winning Grey 3M Windbreaker Zip-Up Jacket

$ 65.00 $ 99.99

SIZE
COLOR
GREY
Quantity
3M REFLECTIVE WATER PROOF 100% POLYESTER MULTIPLE DRAWSTRINGS 6 LOGOS GO UP 1 SIZE FOR A BETTER FIT. (Model is 5'6" 165 lbs wearing a medium.)
Sale
Stay Winning Split Camo Chenille Hoodie Stay Winning Split Camo Chenille Hoodie Quick View

Stay Winning Split Camo Chenille Hoodie

$ 30.00 $ 59.99

SIZE
COLOR
BLACK
Quantity
Chenille patch Print on hood 100% Cotton Side vent
Sale
Stay Winning Westside Neon Black Hoodie Stay Winning Westside Neon Black Hoodie Quick View

Stay Winning Westside Neon Black Hoodie

$ 30.00 $ 64.99

SIZE
COLOR
BLACK
Quantity
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
Stay Winning Script Navy/Yellow Joggers Quick View

Stay Winning Script Navy/Yellow Joggers

$ 30.00 $ 59.99

SIZE
COLOR
BLUE
Quantity
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
Stay Winning OG/Script Logo Navy/Yellow Full Zip-Up Hoodie Stay Winning OG/Script Logo Navy/Yellow Full Zip-Up Hoodie Quick View

Stay Winning OG/Script Logo Navy/Yellow Full Zip-Up Hoodie

$ 30.00 $ 64.99

SIZE
COLOR
BLUE
Quantity
8.5 oz, soft washed 80% Cotton 20% Polyester 3-End Yarn Silver Metal Zipper w/"scuba" hood
Sale
Stay Winning Script Navy/Red Joggers Quick View

Stay Winning Script Navy/Red Joggers

$ 30.00 $ 59.99

SIZE
COLOR
BLUE
Quantity
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
Stay Winning OG/Script Logo Navy/Red Full Zip-Up Hoodie Stay Winning OG/Script Logo Navy/Red Full Zip-Up Hoodie Quick View

Stay Winning OG/Script Logo Navy/Red Full Zip-Up Hoodie

$ 30.00 $ 64.99

SIZE
COLOR
BLUE
Quantity
8.5 oz, soft washed 80% Cotton 20% Polyester 3-End Yarn Silver Metal Zipper w/"scuba" hood
Sale
Stay Winning Script Black/Neon Yellow Joggers Quick View

Stay Winning Script Black/Neon Yellow Joggers

$ 30.00 $ 59.99

SIZE
COLOR
BLACK
Quantity
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
Stay Winning OG/Script Logo Black/Neon Yellow Full Zip-Up Hoodie Stay Winning OG/Script Logo Black/Neon Yellow Full Zip-Up Hoodie Quick View

Stay Winning OG/Script Logo Black/Neon Yellow Full Zip-Up Hoodie

$ 30.00 $ 64.99

SIZE
COLOR
BLACK
Quantity
8.5 oz, soft washed 80% Cotton 20% Polyester 3-End Yarn Silver Metal Zipper w/"scuba" hood
Sale
Stay Winning Women SW Logo Gold Embroidered Marled Ash Joggers Stay Winning Women SW Logo Gold Embroidered Marled Ash Joggers Quick View

Stay Winning Women SW Logo Gold Embroidered Marled Ash Joggers

$ 30.00 $ 59.99

SIZE
COLOR
BLACK
Quantity
Slim fit, flat draw-cord, front side pockets & a single back patch pocket. Finely-knit 3-end French Terry 65/35 cotton/polyester 8.0 oz. y...
Sale
Stay Winning Women Script Logo Gold Embroidered Marled Ash Hoodie Stay Winning Women Script Logo Gold Embroidered Marled Ash Hoodie Quick View

Stay Winning Women Script Logo Gold Embroidered Marled Ash Hoodie

$ 30.00 $ 64.99

SIZE
COLOR
BLACK
Quantity
Double lined hood, pouch pocket, flat draw-cord, side-seamed w/ satin neck taping. Finely-knit 3-end French Terry 65/35 cotton/polyester 8.0 oz...
Sale
Stay Winning Women SW Logo Gold Embroidered Dusty Rose Joggers Quick View

Stay Winning Women SW Logo Gold Embroidered Dusty Rose Joggers

$ 30.00 $ 59.99

SIZE
COLOR
PINK
Quantity
Slim fit, flat draw-cord, front side pockets & a single back patch pocket. Finely-knit 3-end French Terry 65/35 cotton/polyester 8.0 oz. y...
Sale
Stay Winning Maroon/Black Track Pants Stay Winning Maroon/Black Track Pants Quick View

Stay Winning Maroon/Black Track Pants

$ 30.00 $ 44.99

SIZE
COLOR
MAROON
Quantity
100% Recycled Polyester Tricot Imported Front zipper pockets Drawcord on elastic waist Slim fit
Sale
Stay Winning Maroon/Black Track Jacket Stay Winning Maroon/Black Track Jacket Quick View

Stay Winning Maroon/Black Track Jacket

$ 30.00 $ 64.99

SIZE
COLOR
MAROON
Quantity
100% Recycled Polyester Tricot Imported Regular fit strikes a comfortable balance between loose and snug Stand-up collar for coverage Full zip let...
Stay Winning Black Toddler Script Tee Quick View

Stay Winning Black Toddler Script Tee

$ 20.00

SIZE
COLOR
BLACK
Quantity
Fabric 30 single 4.3 oz. Soft-washed 100% combed ring-spun cotton 60% cotton / 40% polyester Features Unisex Ultra soft hand Side-seamed Tightly...
Stay Winning Mint Toddler Script Tee Quick View

Stay Winning Mint Toddler Script Tee

$ 20.00

SIZE
COLOR
MINT
Quantity
Fabric 30 single 4.3 oz. Soft-washed 100% combed ring-spun cotton 60% cotton / 40% polyester Features Unisex Ultra soft hand Side-seamed Tightly...
Stay Winning Grey Heather Toddler Script Tee Quick View

Stay Winning Grey Heather Toddler Script Tee

$ 20.00

SIZE
COLOR
GREY
Quantity
Fabric 4.3 oz. Soft-washed 100% combed ring-spun cotton 60% cotton / 40% polyester Features Unisex Ultra soft hand Side-seamed Tightly knit Stan...
Stay Winning Hot Pink Toddler Tee Stay Winning Hot Pink Toddler Tee Quick View

Stay Winning Hot Pink Toddler Tee

$ 20.00

SIZE
COLOR
PINK
Quantity
Fabric 30 single 4.3 oz. Soft-washed 100% combed ring-spun cotton 60% cotton / 40% polyester Features Unisex Ultra soft hand Side-seamed Tightly...
Sale
Stay Winning Youth Black Script Tee Quick View

Stay Winning Youth Black Script Tee

$ 20.00 $ 24.99

SIZE
COLOR
BLACK
Quantity
Fabric 30 single 4.3 oz. Soft-washed 100% combed ring-spun cotton 60% cotton / 40% polyester Features Unisex Ultra soft hand Side-seamed Tightly...
Sale
Stay Winning Youth Green Script Tee Quick View

Stay Winning Youth Green Script Tee

$ 20.00 $ 24.99

SIZE
COLOR
GREEN
Quantity
Fabric 30 single 4.3 oz. Soft-washed 100% combed ring-spun cotton 60% cotton / 40% polyester Features Unisex Ultra soft hand Side-seamed Tightly...
Sale
Stay Winning Youth Grey Heather Script Tee Quick View

Stay Winning Youth Grey Heather Script Tee

$ 20.00 $ 24.99

SIZE
COLOR
GREY
Quantity
Fabric 30 single 4.3 oz. Soft-washed 100% combed ring-spun cotton 60% cotton / 40% polyester Features Unisex Ultra soft hand Side-seamed Tightly...
Sale
Stay Winning Youth Hot Pink Script Tee Quick View

Stay Winning Youth Hot Pink Script Tee

$ 20.00 $ 24.99

SIZE
COLOR
PINK
Quantity
Fabric 30 single 4.3 oz. Soft-washed 100% combed ring-spun cotton 60% cotton / 40% polyester Features Unisex Ultra soft hand Side-seamed Tightly...
Sale
Stay Winning Elvira Pink Crop Top Sweater Quick View

Stay Winning Elvira Pink Crop Top Sweater

$ 30.00 $ 39.99

SIZE
COLOR
PINK
Quantity
Made of high quality cotton blended fabric, soft and smooth Crop top, long sleeve, loose casual, round neck pullover, prefect for womens, teens an...
Sale
Stay Winning Elvira Black Crop Top Sweater Quick View

Stay Winning Elvira Black Crop Top Sweater

$ 30.00 $ 39.99

SIZE
COLOR
BLACK
Quantity
Made of high quality cotton blended fabric, soft and smooth Crop top, long sleeve, loose casual, round neck pullover, prefect for womens, teens an...
Sale
Stay Winning French Water Black Tee Stay Winning French Water Black Tee Quick View

Stay Winning French Water Black Tee

$ 20.00 $ 34.99

SIZE
COLOR
BLACK
Quantity
100% Combed Ring-Spun Cotton. Soft-Washed. 
Sale
Stay Winning Black/White Dad Hat Stay Winning Black/White Dad Hat Quick View

Stay Winning Black/White Dad Hat

$ 20.00 $ 29.99

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

Stay Winning Black/White Dad Hat

$ 20.00
$ 29.99
Sale
Stay Winning French Water Black Tank Top Stay Winning French Water Black Tank Top Quick View

Stay Winning French Water Black Tank Top

$ 20.00 $ 29.99

SIZE
COLOR
BLACK
Quantity
100% Combed Ring-Spun Cotton. Soft-Washed. 

Join Our Mailing List