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

Stay Winning Open End Embroidered Sweats Stay Winning Open End Embroidered Sweats Quick View

Stay Winning Open End Embroidered Sweats

$ 50.00

Color
Gray
Red
Size
Quantity
100% cotton Embroidery 320 GSM / 9.44 oz Back zipper pocket Side zipper pockets Open end bottom Pre-shrunk for minimum shrinkage
Stay Winning Embroidered Flare Sweatpants Stay Winning Embroidered Flare Sweatpants Quick View

Stay Winning Embroidered Flare Sweatpants

$ 50.00

Color
Black
Red
Gray
Size
Quantity
100% cotton Embroidery True to size fit 320 GSM / 9.44 oz Back zipper pocket Side zipper pockets
Stay Winning Chi-Town Black Tee Stay Winning Chi-Town Black Tee Quick View

Stay Winning Chi-Town Black Tee

$ 45.00

SIZE
COLOR
BLACK
Quantity
100% Cotton. Pre-shrunk material. For best results machine wash inside out warm, hang dry & iron inside out.
Stay Winning Chi-Town Jacket Quick View

Stay Winning Chi-Town Jacket

$ 100.00

Size
Quantity
35% cotton 65% polyester tapestry 2 side pockets True to size

Stay Winning Chi-Town Jacket

$ 100.00
Stay Winning Chi-Town Shorts Quick View

Stay Winning Chi-Town Shorts

$ 65.00

Size
Quantity
35% cotton 65% polyester tapestry 2 side pockets True to size
Stay Winning Corleon Jacket Stay Winning Corleon Jacket Quick View

Stay Winning Corleon Jacket

$ 100.00

Size
Quantity
35% cotton 65% polyester tapestry 2 side pockets True to size

Stay Winning Corleon Jacket

$ 100.00
Stay Winning Family Over Everything Escobar Zip Up Hoodie Stay Winning Family Over Everything Escobar Zip Up Hoodie Quick View

Stay Winning Family Over Everything Escobar Zip Up Hoodie

$ 100.00

Size
Quantity
35% cotton 65% polyester tapestry 2 side pockets True to size
Stay Winning Family Over Everything Mobfather Zip Up Hoodie Stay Winning Family Over Everything Mobfather Zip Up Hoodie Quick View

Stay Winning Family Over Everything Mobfather Zip Up Hoodie

$ 100.00

Size
Quantity
35% cotton 65% polyester tapestry 2 side pockets
Stay Winning Champion Shorts Stay Winning Champion Shorts Quick View

Stay Winning Champion Shorts

$ 65.00

Size
Quantity
35% cotton 65% polyester tapestry 2 side pockets True to size
Stay Winning Champion Zip Up Hoodie Stay Winning Champion Zip Up Hoodie Quick View

Stay Winning Champion Zip Up Hoodie

$ 100.00

Size
Quantity
35% cotton 65% polyester tapestry 2 side pockets True to size
Stay Winning Navy Blue Wool Jacket Stay Winning Navy Blue Wool Jacket Quick View

Stay Winning Navy Blue Wool Jacket

$ 180.00

Color
Size
Quantity
Embroidery & chenille Original wool
Stay Winning Navy Blue Bubbas Varsity Jacket Stay Winning Navy Blue Bubbas Varsity Jacket Quick View

Stay Winning Navy Blue Bubbas Varsity Jacket

$ 200.00

Color
Size
Quantity
Embroidery & chenille Sheep leather Original wool
Stay Winning Royalty Black Wool Jacket Stay Winning Royalty Black Wool Jacket Quick View

Stay Winning Royalty Black Wool Jacket

$ 180.00

Color
Black
Size
Quantity
Embroidery & chenille Original wool Gold zippers
Stay Winning Black Leather Jacket Stay Winning Black Leather Jacket Quick View

Stay Winning Black Leather Jacket

$ 300.00

Color
Black
Size
Quantity
Fully embroidered 100% genuine cow leather Go up one size for a better fit
Floats EGO Trends 3373 Sunglasses Floats EGO Trends 3373 Sunglasses Quick View

Floats EGO Trends 3373 Sunglasses

$ 30.00

Temple color
Gold
Black
Red
White
Quantity
These sunglasses feature a bold, oversized square frame with a sleek, modern aesthetic. The wide temples are accented with a unique embossed emblem...
Floats EGO Trends 3374 Sunglasses Floats EGO Trends 3374 Sunglasses Quick View

Floats EGO Trends 3374 Sunglasses

$ 30.00

Temple color
Gold
Black
Beige
White
Quantity
Bold. Sleek. Timeless. These statement sunglasses feature a sharp, modern silhouette with a structured frame that exudes confidence. Designed for b...
Stay Winning Sticker Quick View

Stay Winning Sticker

$ 2.00

Quantity
1 Random Sticker

Stay Winning Sticker

$ 2.00
Stay Winning Bay Area Keychain Quick View

Stay Winning Bay Area Keychain

$ 10.00

Quantity
Approximately the size of a half dollar Bay Area logo is size of a quarter Limited Edition
Stay Winning Sticker Pack Quick View

Stay Winning Sticker Pack

$ 5.00

Quantity
3 Random Stickers
Stay Winning Cork Popper Gang Miami Club Poster Quick View

Stay Winning Cork Popper Gang Miami Club Poster

$ 10.00

Quantity
By the late Steve Nazar Tony Montana & Manolo 18"x24"
Stay Winning Embroidered SW Logo Cursive Hoodie Stay Winning Embroidered SW Logo Cursive Hoodie Quick View

Stay Winning Embroidered SW Logo Cursive Hoodie

$ 65.00

Size
Color
Black
Red
Gray
Quantity
100% cotton Embroidery 320 GSM / 9.44 oz Pre-shrunk for minimum shrinkage Relaxed fit, go down one size for snug look
Stay Winning Original Script Crewneck Women Sweater Stay Winning Original Script Crewneck Women Sweater Quick View

Stay Winning Original Script Crewneck Women Sweater

$ 55.00

Color
Black
Blue
Yellow
Size
Quantity
Relaxed fit Pullover crew, drop shoulder, crew neck Mid weight, 9.4oz 80% cotton 20% recycled polyester anti-pill fleece, sleeve cuff ribbing
Stay Winning Original Script Youth Hoodie Stay Winning Original Script Youth Hoodie Quick View

Stay Winning Original Script Youth Hoodie

$ 45.00

Color
Red
Black
Blue
Gray
Size
Quantity
Unisex. Ultra soft hand. Side-seamed. Tightly knit. 2-panel hood. Ribbing at cuffs and waistband made with lycra for long lasting performance. S(7...
Stay Winning Black/Red Snapback Hat Stay Winning Black/Red Snapback Hat Quick View

Stay Winning Black/Red Snapback Hat

$ 45.00

Quantity
5 panel Curved bill Premium wool  Fully embroidered Gold pin
Stay Winning Red Trucker Hat Stay Winning Red Trucker Hat Quick View

Stay Winning Red Trucker Hat

$ 45.00

Quantity
Embroidered White back strap Foam / Mesh Trucker
Stay Winning Original SW Script Logo Red/White Long Sleeve Tee Stay Winning Original SW Script Logo Red/White Long Sleeve Tee Quick View

Stay Winning Original SW Script Logo Red/White Long Sleeve Tee

$ 45.00

Size
Color
Red
Quantity
5.5 oz soft-washed, combed ring-spun fabric 100% combed ring-spun cotton Substantial ribbed cuffs
Sale
Stay Winning Bart The Menace Pocket Tee Stay Winning Bart The Menace Pocket Tee Quick View

Stay Winning Bart The Menace Pocket Tee

$ 10.00 $ 31.99

Color
Size
Quantity
Go up one size for a better fit
Sale
Stay Winning 1981 Trophy Beige Tee Stay Winning 1981 Trophy Beige Tee Quick View

Stay Winning 1981 Trophy Beige Tee

$ 10.00 $ 31.99

Color
Beige
Size
Quantity
100% Cotton

Stay Winning 1981 Trophy Beige Tee

$ 10.00
$ 31.99
Sale
Stay Winning Frostiez Black Tee Stay Winning Frostiez Black Tee Quick View

Stay Winning Frostiez Black Tee

$ 20.00 $ 44.99

Color
Black
Size
Quantity
100% Cotton

Stay Winning Frostiez Black Tee

$ 20.00
$ 44.99
Sale
Stay Winning Golden State Winners Blue Tee Stay Winning Golden State Winners Blue Tee Quick View

Stay Winning Golden State Winners Blue Tee

$ 10.00 $ 31.99

Color
Blue
Size
Quantity
100% cotton
Sale
Stay Winning Cork Popper Gang Navy Sweat Shorts Quick View

Stay Winning Cork Popper Gang Navy Sweat Shorts

$ 15.00 $ 29.99

Color
Size
Quantity
100% Cotton
Sale
Stay Winning Green Killa Kali Black Pocket Tee Quick View

Stay Winning Green Killa Kali Black Pocket Tee

$ 10.00 $ 29.99

Color
Black
Size
Quantity
1" side vents Suggest to go up one size for a perfect fit
Sale
Stay Winning Maroon Paisley Black Pocket Tee Quick View

Stay Winning Maroon Paisley Black Pocket Tee

$ 10.00 $ 29.99

Color
Black
Size
Quantity
1" side vents Suggest to go up one size for a perfect fit
Sale
Stay Winning Black Crop Top Tee Quick View

Stay Winning Black Crop Top Tee

$ 20.00 $ 31.99

SIZE
COLOR
BLACK
Quantity
Relaxed fit.  Crew neck. 100% combed cotton. Short body, dropped shoulders, neck ribbing, side seamed, shoulder to shoulder tape, double needle he...

Stay Winning Black Crop Top Tee

$ 20.00
$ 31.99
Stay Winning Original SW Script Logo White Tee Stay Winning Original SW Script Logo White Tee Quick View

Stay Winning Original SW Script Logo White Tee

$ 40.00

Size
Color
White
Quantity
5.5 oz, 20 Singles 100% Combed Ringspun Cotton
Stay Winning Original SW Script Logo Black Tee Stay Winning Original SW Script Logo Black Tee Quick View

Stay Winning Original SW Script Logo Black Tee

$ 40.00

Size
Color
Black
Quantity
5.5 oz, 20 Singles 100% Combed Ringspun Cotton
Stay Winning Original SW Script Logo Navy Blue Long Sleeve Tee Stay Winning Original SW Script Logo Navy Blue Long Sleeve Tee Quick View

Stay Winning Original SW Script Logo Navy Blue Long Sleeve Tee

$ 45.00

Size
Color
Quantity
5.5 oz soft-washed, combed ring-spun fabric 100% combed ring-spun cotton Substantial ribbed cuffs
Stay Winning Original SW Script Logo Pink Tee Stay Winning Original SW Script Logo Pink Tee Quick View

Stay Winning Original SW Script Logo Pink Tee

$ 40.00

Size
Color
Pink
Quantity
5.5 oz, 20 Singles 100% Combed Ringspun Cotton
Stay Winning Original SW Script Logo Grey Hoodie Stay Winning Original SW Script Logo Grey Hoodie Quick View

Stay Winning Original SW Script Logo Grey Hoodie

$ 50.00

Size
Color
Gray
Quantity
8.0 oz 50% Cotton/50% Poly NuBlend® Pre-shrunk Fleece Seamless body with set-in sleeves Matching drawcord Double-ply hood with grommets Front muf...
Stay Winning Original SW Script Logo White Hoodie Stay Winning Original SW Script Logo White Hoodie Quick View

Stay Winning Original SW Script Logo White Hoodie

$ 65.00

Size
Color
White
Quantity
8.5 oz Soft-Washed Comfort Weight Fleece 65% Ringspun Cotton 35% Polyester, 3-end yarn Flat draw cords
Stay Winning Original SW Script Logo Olive Hoodie Stay Winning Original SW Script Logo Olive Hoodie Quick View

Stay Winning Original SW Script Logo Olive Hoodie

$ 65.00

Size
Color
Green
Quantity
8.5 oz Soft-Washed Comfort Weight Fleece 65% Ringspun Cotton 35% Polyester, 3-end yarn Flat draw cords
Stay Winning The North Cal Pink Jacket Stay Winning The North Cal Pink Jacket Quick View

Stay Winning The North Cal Pink Jacket

$ 80.00

Size
Quantity
100% Polyester Detachable hoodie Zipper pockets Go up one size for a looser fit (slim) Drawstrings  Water-resistant Transfer print Limited quantity
Stay Winning The North Cal Olive Jacket Stay Winning The North Cal Olive Jacket Quick View

Stay Winning The North Cal Olive Jacket

$ 80.00

Size
Quantity
100% Polyester Detachable hoodie Zipper pockets Go up one size for a looser fit (slim) Drawstrings  Water-resistant Transfer print Limited quantity
Stay Winning The North Cal Cream Jacket Stay Winning The North Cal Cream Jacket Quick View

Stay Winning The North Cal Cream Jacket

$ 80.00

Size
Quantity
100% Polyester Detachable hoodie Zipper pockets Go up one size for a looser fit (slim) Drawstrings  Water-resistant Transfer print Limited quantity
Stay Winning Embroidered Zipper Sweats Stay Winning Embroidered Zipper Sweats Quick View

Stay Winning Embroidered Zipper Sweats

$ 45.00

Size
Color
Blue
Black
Quantity
100% cotton Embroidery 320 GSM / 9.44 oz Back zipper pocket Side zipper pockets Bottom zippers Pre-shrunk for minimum shrinkage
Stay Winning Knowledge Royal Blue Hoodie Stay Winning Knowledge Royal Blue Hoodie Quick View

Stay Winning Knowledge Royal Blue Hoodie

$ 65.00

SIZE
Quantity
100% cotton Chenille embroidery 320 GSM / 9.44 oz Pre-shrunk for minimum shrinkage
Stay Winning x Supdawk Cream Snapback Hat Stay Winning x Supdawk Cream Snapback Hat Quick View

Stay Winning x Supdawk Cream Snapback Hat

$ 60.00

Quantity
Stay Winning x Supdawk 5 panel Curved bill Premium wool  Fully embroidered Gold pin
Stay Winning Cork Popper Gang Snapback Hat Stay Winning Cork Popper Gang Snapback Hat Quick View

Stay Winning Cork Popper Gang Snapback Hat

$ 60.00

Quantity
5-panel snapback Mesh back panels Wool front panels Fully embroidered w/ chenille

Join Our Mailing List