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.

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Sale
Stay Winning Never Losing Trophy Black Tee Stay Winning Never Losing Trophy Black Tee Quick View

Stay Winning Never Losing Trophy Black Tee

$ 19.99 $ 35.99

SIZE
COLOR
BLACK
Quantity
100% Cotton Enzyme wash for an ultra soft feel.
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Stay Winning Never Losing Trophy Black Tee
$ 19.99
$ 35.99
Sale
Stay Winning Rising Sun Coral Tee Stay Winning Rising Sun Coral Tee Quick View

Stay Winning Rising Sun Coral Tee

$ 19.99 $ 39.99

SIZE
COLOR
ORANGE
Quantity
"Rising Sun" means Rising Funds... Exclusive drop from STAY WINNING! Only 95 Tees each color made so everyone can't have one! Created by the Wi...
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Stay Winning Rising Sun Coral Tee
$ 19.99
$ 39.99
Sale
Stay Winning Rising Sun Navy Tee Stay Winning Rising Sun Navy Tee Quick View

Stay Winning Rising Sun Navy Tee

$ 19.99 $ 39.99

SIZE
COLOR
BLUE
Quantity
"Rising Sun" means Rising Funds... Exclusive drop from STAY WINNING! Only 95 Tees each color made so everyone can't have one! Created by the Winne...
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Stay Winning Rising Sun Navy Tee
$ 19.99
$ 39.99
Sale
Stay Winning Never Losing "No Games" Black Tee Stay Winning Never Losing "No Games" Black Tee Quick View

Stay Winning Never Losing "No Games" Black Tee

$ 19.99 $ 39.99

SIZE
COLOR
BLACK
Quantity
Crafted in a modern cut that sits on the body for a clean silhouette, soft lightweight fabric has you covered for that timeless easy to go look...
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Stay Winning Never Losing "No Games" Black Tee
$ 19.99
$ 39.99
Sale
Stay Winning Original Logo/Script Red/White Varsity Jacket Stay Winning Original Logo/Script Red/White Varsity Jacket Quick View

Stay Winning Original Logo/Script Red/White Varsity Jacket

$ 59.99 $ 79.99

SIZE
COLOR
RED
Quantity
Front button snap closure, dual side pockets & contrasting rib-trim at the collar cuffs plus bottom hem. A soft terry style version of the cla...
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Stay Winning Original Logo/Script Red/White Varsity Jacket
$ 59.99
$ 79.99
Sale
Stay Winning Original Logo/Script Blue/White Varsity Jacket Stay Winning Original Logo/Script Blue/White Varsity Jacket Quick View

Stay Winning Original Logo/Script Blue/White Varsity Jacket

$ 59.99 $ 79.99

SIZE
COLOR
BLUE
Quantity
Front button snap closure, dual side pockets & contrasting rib-trim at the collar cuffs plus bottom hem. A soft terry style version of the cla...
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Stay Winning Original Logo/Script Blue/White Varsity Jacket
$ 59.99
$ 79.99
Sale
Stay Winning Original Logo/Script Grey/White Varsity Jacket Stay Winning Original Logo/Script Grey/White Varsity Jacket Quick View

Stay Winning Original Logo/Script Grey/White Varsity Jacket

$ 59.99 $ 79.99

SIZE
COLOR
GREY
Quantity
Front button snap closure, dual side pockets & contrasting rib-trim at the collar cuffs plus bottom hem. A soft terry style version of the cl...
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Stay Winning Original Logo/Script Grey/White Varsity Jacket
$ 59.99
$ 79.99
Sale
Stay Winning Original Logo/Script Maroon/White Varsity Jacket Stay Winning Original Logo/Script Maroon/White Varsity Jacket Quick View

Stay Winning Original Logo/Script Maroon/White Varsity Jacket

$ 59.99 $ 79.99

SIZE
COLOR
MAROON
Quantity
Front button snap closure, dual side pockets & contrasting rib-trim at the collar cuffs plus bottom hem. A soft terry style version of the cla...
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Stay Winning Original Logo/Script Maroon/White Varsity Jacket
$ 59.99
$ 79.99
Sale
Stay Winning Hyphy By Nature Navy/Red Tee Stay Winning Hyphy By Nature Navy/Red Tee Quick View

Stay Winning Hyphy By Nature Navy/Red Tee

$ 19.99 $ 39.99

SIZE
COLOR
BLUE
Quantity
Crafted in a modern cut that sits on the body for a clean silhouette, soft lightweight fabric has you covered for that timeless easy to go look. ...
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Stay Winning Hyphy By Nature Navy/Red Tee
$ 19.99
$ 39.99
Sale
Stay Winning Hyphy By Nature Black/White Tee Stay Winning Hyphy By Nature Black/White Tee Quick View

Stay Winning Hyphy By Nature Black/White Tee

$ 19.99 $ 39.99

SIZE
COLOR
BLACK
Quantity
Stay Winning Hyphy By Nature Black/White Tee Crafted in a modern cut that sits on the body for a clean silhouette, soft lightweight fabric has ...
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Stay Winning Hyphy By Nature Black/White Tee
$ 19.99
$ 39.99
Sale
Stay Winning Double Dragon Black Tee Stay Winning Double Dragon Black Tee Quick View

Stay Winning Double Dragon Black Tee

$ 19.99 $ 29.99

SIZE
COLOR
BLACK
Quantity
Crafted in a modern cut that sits on the body for a clean silhouette, soft lightweight fabric has you covered for that timeless easy to go look. ...
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Stay Winning Double Dragon Black Tee
$ 19.99
$ 29.99
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Stay Winning Original Logo Olive/White Crewneck Sweater Stay Winning Original Logo Olive/White Crewneck Sweater Quick View

Stay Winning Original Logo Olive/White Crewneck Sweater

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SIZE
COLOR
GREEN
Comfort Weight Fleece 8.5 oz 80% Cotton 20% Polyester, Soft-washed Unisex
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Stay Winning Original Logo Olive/White Crewneck Sweater
$ 29.99
$ 49.99
Sale
Stay Winning Original Logo Navy/White Crewneck Sweater Stay Winning Original Logo Navy/White Crewneck Sweater Quick View

Stay Winning Original Logo Navy/White Crewneck Sweater

$ 29.99 $ 54.99

SIZE
COLOR
NAVY
Quantity
Stay Winning Original Logo Navy/White Crewneck Sweater Comfort Weight Fleece 8.5 oz 80% Cotton 20% Polyester, Soft-washed Unisex
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Stay Winning Original Logo Navy/White Crewneck Sweater
$ 29.99
$ 54.99
Sale
Stay Winning Script Black/White Camo Hoodie Stay Winning Script Black/White Camo Hoodie Quick View

Stay Winning Script Black/White Camo Hoodie

$ 29.99 $ 49.99

SIZE
COLOR
BLACK
Quantity
Custom gold tip laces Gold side zippers Hand pockets on front 80% cotton 20% polyester Made in Pakistan
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Stay Winning Script Black/White Camo Hoodie
$ 29.99
$ 49.99
Sale
Stay Winning Script Red/White Camo Hoodie Stay Winning Script Red/White Camo Hoodie Quick View

Stay Winning Script Red/White Camo Hoodie

$ 29.99 $ 64.99

SIZE
COLOR
RED
Quantity
Custom gold tip laces Gold side zippers Hand pockets on front 80% cotton 20% polyester Made in Pakistan
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Stay Winning Script Red/White Camo Hoodie
$ 29.99
$ 64.99
Sale
Stay Winning Script Navy/White Camo Hoodie Stay Winning Script Navy/White Camo Hoodie Quick View

Stay Winning Script Navy/White Camo Hoodie

$ 29.99 $ 64.99

SIZE
COLOR
BLUE
Quantity
Custom gold tip laces Gold side zippers Hand pockets on front 80% cotton 20% polyester Made in Pakistan
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Stay Winning Script Navy/White Camo Hoodie
$ 29.99
$ 64.99
Sale
Stay Winning Never Losing El Chapo Navy Tee Stay Winning Never Losing El Chapo Navy Tee Quick View

Stay Winning Never Losing El Chapo Navy Tee

$ 19.99 $ 39.99

SIZE
COLOR
BLUE
Quantity
Fine Knit  4.3 oz 100% Ringspun Cotton Exclusive limited print Product Description : El Chapo Guzman de Sinalo, Mexico as seen on Narcos. 
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Stay Winning Never Losing El Chapo Navy Tee
$ 19.99
$ 39.99
Sale
Stay Winning Never Losing Godmother Maroon Tee Stay Winning Never Losing Godmother Maroon Tee Quick View

Stay Winning Never Losing Godmother Maroon Tee

$ 19.99 $ 39.99

SIZE
COLOR
MAROON
Quantity
Fine Knit  4.3 oz 100% Ringspun Cotton Exclusive limited print Product Description : Griselda Blanco de Medellin, Columbia w/ Charles Cosby of Eas...
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Stay Winning Never Losing Godmother Maroon Tee
$ 19.99
$ 39.99
Sale
Stay Winning Spend Money Green Tee Stay Winning Spend Money Green Tee Quick View

Stay Winning Spend Money Green Tee

$ 19.99 $ 39.99

SIZE
COLOR
GREEN
Quantity
5.5 oz 100% Combed Ringspun Cotton
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Stay Winning Spend Money Green Tee
$ 19.99
$ 39.99
Sale
Stay Winning Script Red Tank Top Quick View

Stay Winning Script Red Tank Top

$ 19.99 $ 29.99

SIZE
COLOR
RED
Quantity
Description: Red tank top with original Stay Winning Script in white on front, solid back. Fabric: 5.5 oz. 100% Combed Ring-Spun Cotton, Soft-Washed.
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Stay Winning Script Red Tank Top
$ 19.99
$ 29.99
Sale
Stay Winning Script Navy Tank Top Quick View

Stay Winning Script Navy Tank Top

$ 19.99 $ 29.99

SIZE
COLOR
BLUE
Quantity
Description: Navy tank top with original Stay Winning Script in white on front, solid back.  Fabric: 5.5 oz. 100% Combed Ring-Spun Cotton, Soft-Was...
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Stay Winning Script Navy Tank Top
$ 19.99
$ 29.99
Sale
Stay Winning Script White Tank Top Quick View

Stay Winning Script White Tank Top

$ 19.99 $ 29.99

SIZE
COLOR
WHITE
Quantity
Description: White tank top with original Stay Winning Script in black on front, solid back. Fabric: 5.5 oz. 100% Combed Ring-Spun Cotton, Soft-Was...
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Stay Winning Script White Tank Top
$ 19.99
$ 29.99
Sale
Stay Winning Original Logo White/Red Elongated Scoop Tee Stay Winning Original Logo White/Red Elongated Scoop Tee Quick View

Stay Winning Original Logo White/Red Elongated Scoop Tee

$ 19.99 $ 24.99

SIZE
COLOR
WHITE
Quantity
Ultra Soft Hand, Tightly Knit Side-Seamed 4.3 oz 30 Singles 100% Combed Ringspun Cotton, Soft-Washed The length is 2 inches longer than standard ...
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Stay Winning Original Logo White/Red Elongated Scoop Tee
$ 19.99
$ 24.99
Sale
Stay Winning Original Logo Maroon Elongated Scoop Tee Stay Winning Original Logo Maroon Elongated Scoop Tee Quick View

Stay Winning Original Logo Maroon Elongated Scoop Tee

$ 19.99 $ 24.99

SIZE
COLOR
MAROON
Quantity
Ultra Soft Hand, Tightly Knit Side-Seamed 4.3 oz 30 Singles 100% Combed Ringspun Cotton, Soft-Washed The length is 2 inches longer than standard ...
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Stay Winning Original Logo Maroon Elongated Scoop Tee
$ 19.99
$ 24.99
Stay Winning Baby Blue Infant Onesie Quick View

Stay Winning Baby Blue Infant Onesie

$ 19.99

SIZE
COLOR
BLUE
Quantity
100% Baby Rib cotton construction  Shrinkage: will shrink an average of one size when put in the dryer Unisex Fabric weight 5.8 oz/yd² (197 g/m²) ...
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Stay Winning Baby Blue Infant Onesie
$ 19.99
Sale
Stay Winning Bay Area Grey Tee Stay Winning Bay Area Grey Tee Quick View

Stay Winning Bay Area Grey Tee

$ 19.99 $ 29.99

SIZE
COLOR
GREY
Quantity
Crafted in a modern cut that sits on the body for a clean silhouette Our soft lightweight fabric has you covered for that timeless easy to go loo...
View Full Details

Stay Winning Bay Area Grey Tee
$ 19.99
$ 29.99
Sale
Stay Winning Scarface Cork Popper Gang Maroon Tee Quick View

Stay Winning Scarface Cork Popper Gang Maroon Tee

$ 19.99 $ 29.99

SIZE
COLOR
MAROON
Quantity
Crafted in a modern cut that sits on the body for a clean silhouette, our soft lightweight fabric has you covered for that timeless easy to go lo...
View Full Details

Stay Winning Scarface Cork Popper Gang Maroon Tee
$ 19.99
$ 29.99
Sale
Stay Winning Scarface Cork Popper Gang Red Tee Quick View

Stay Winning Scarface Cork Popper Gang Red Tee

$ 19.99 $ 29.99

SIZE
COLOR
RED
Quantity
Crafted in a modern cut that sits on the body for a clean silhouette, our soft lightweight fabric has you covered for that timeless easy to go lo...
View Full Details

Stay Winning Scarface Cork Popper Gang Red Tee
$ 19.99
$ 29.99
Sale
Stay Winning Scarface Cork Popper Gang Black Tee Quick View

Stay Winning Scarface Cork Popper Gang Black Tee

$ 19.99 $ 29.99

SIZE
COLOR
BLACK
Quantity
Crafted in a modern cut that sits on the body for a clean silhouette, our soft lightweight fabric has you covered for that timeless easy to go lo...
View Full Details

Stay Winning Scarface Cork Popper Gang Black Tee
$ 19.99
$ 29.99
Sale
Stay Winning Cartel Angel Crew Neck Sweater Stay Winning Cartel Angel Crew Neck Sweater Quick View

Stay Winning Cartel Angel Crew Neck Sweater

$ 29.99 $ 49.99

SIZE
COLOR
BLACK
Quantity
Front hand pockets w/zippers Raglan fit 100% cotton  Made in Pakistan  
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Stay Winning Cartel Angel Crew Neck Sweater
$ 29.99
$ 49.99
Sale
Stay Winning Never Losing Navy Slides Stay Winning Never Losing Navy Slides Quick View

Stay Winning Never Losing Navy Slides

$ 19.99 $ 39.99

SIZE
COLOR
BLUE
Quantity
Sizes 7-13 Slip resistant Black/gold dust bag
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Stay Winning Never Losing Navy Slides
$ 19.99
$ 39.99
Sale
Stay Winning Air Americano Slides Stay Winning Air Americano Slides Quick View

Stay Winning Air Americano Slides

$ 19.99 $ 39.99

SIZE
COLOR
RED
Quantity
Slip resistant Black/gold dust bag Sizes 7-13
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Stay Winning Air Americano Slides
$ 19.99
$ 39.99
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Stay Winning SW Red Slides Stay Winning SW Red Slides Quick View

Stay Winning SW Red Slides

Sold Out

SIZE
COLOR
RED
Sizes 7-13 Slip resistant Black/gold dust bag
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Stay Winning SW Red Slides
$ 39.99
Sale
Stay Winning Warriors Blue Tee Stay Winning Warriors Blue Tee Quick View

Stay Winning Warriors Blue Tee

$ 19.99 $ 39.99

SIZE
COLOR
BLUE
Quantity
4.3 oz 100% Deluxe combed ringspun cotton. 50/50 Cotton Polyester Pre-shrunk to minimize shrink
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Stay Winning Warriors Blue Tee
$ 19.99
$ 39.99
Sale
Stay Winning x Meet The Dealers Coast To Coast Reversible Jacket Stay Winning x Meet The Dealers Coast To Coast Reversible Jacket Quick View

Stay Winning x Meet The Dealers Coast To Coast Reversible Jacket

$ 89.99 $ 159.99

SIZE
COLOR
BLUE
Quantity
Fully embroidered logos. West Coast Stay Winning side champagne bottle representing success w/ a Toast to the good life. East Coast Meet The Deale...
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Stay Winning x Meet The Dealers Coast To Coast Reversible Jacket
$ 89.99
$ 159.99
Sale
Stay Winning Black/Navy Soccer Polo Tee Stay Winning Black/Navy Soccer Polo Tee Quick View

Stay Winning Black/Navy Soccer Polo Tee

$ 19.99 $ 59.99

SIZE
COLOR
NAVY
Quantity
Cut & Sew 2-tone fabric w/ Embroidery & Patch Designer fit (go up 1 size for a loose fit) 40% Cotton 60% Polyester Dry Fit Material
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Stay Winning Black/Navy Soccer Polo Tee
$ 19.99
$ 59.99
Sale
Stay Winning Black/Pink Soccer Polo Tee Stay Winning Black/Pink Soccer Polo Tee Quick View

Stay Winning Black/Pink Soccer Polo Tee

$ 19.99 $ 59.99

SIZE
COLOR
BLACK
Quantity
40% Cotton 60% Polyester Dry Fit Material Cut & Sew 2-tone fabric w/ Embroidery & Patch Designer fit (go up 1 size for a loose fit)
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Stay Winning Black/Pink Soccer Polo Tee
$ 19.99
$ 59.99
Sale
Stay Winning Cream/Royal Soccer Polo Tee Stay Winning Cream/Royal Soccer Polo Tee Quick View

Stay Winning Cream/Royal Soccer Polo Tee

$ 19.99 $ 59.99

SIZE
COLOR
WHITE
Quantity
40% Cotton 60% Polyester Dry Fit Material Cut & Sew 2-tone fabric w/ Embroidery & Patch Designer fit (go up 1 size for a loose fit)
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Stay Winning Cream/Royal Soccer Polo Tee
$ 19.99
$ 59.99
Sale
Stay Winning Black/Red Soccer Polo Tee Stay Winning Black/Red Soccer Polo Tee Quick View

Stay Winning Black/Red Soccer Polo Tee

$ 19.99 $ 59.99

SIZE
COLOR
BLACK
Quantity
40% Cotton 60% Polyester Dry Fit Material Cut & Sew 2-tone fabric w/ Embroidery & Patch Designer fit (go up 1 size for a loose fit)
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Stay Winning Black/Red Soccer Polo Tee
$ 19.99
$ 59.99
Sale
Stay Winning Red/Navy Soccer Polo Tee Stay Winning Red/Navy Soccer Polo Tee Quick View

Stay Winning Red/Navy Soccer Polo Tee

$ 19.99 $ 59.99

SIZE
COLOR
RED
Quantity
Cut & Sew 2-tone fabric w/ Embroidery & Patch Designer fit (go up 1 size for a loose fit) 40% Cotton 60% Polyester Dry Fit Material
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Stay Winning Red/Navy Soccer Polo Tee
$ 19.99
$ 59.99
Sale
Stay Winning Navy/Yellow Soccer Polo Tee Stay Winning Navy/Yellow Soccer Polo Tee Quick View

Stay Winning Navy/Yellow Soccer Polo Tee

$ 19.99 $ 59.99

SIZE
COLOR
BLUE
Quantity
40% Cotton 60% Polyester Dry Fit Material Cut & Sew 2-tone fabric w/ Embroidery & Patch Designer fit (go up 1 size for a loose fit)
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Stay Winning Navy/Yellow Soccer Polo Tee
$ 19.99
$ 59.99
Sale
Stay Winning Long Sleeve Navy Blue Soccer Polo Tee Stay Winning Long Sleeve Navy Blue Soccer Polo Tee Quick View

Stay Winning Long Sleeve Navy Blue Soccer Polo Tee

$ 19.99 $ 64.99

SIZE
COLOR
NAVY
Quantity
40% Cotton 60% Polyester Dry Fit Material Cut & Sew 2-tone fabric w/ Embroidery & Patch Designer fit (go up 1 size for a loose fit)
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Stay Winning Long Sleeve Navy Blue Soccer Polo Tee
$ 19.99
$ 64.99
Sale
Stay Winning Long Sleeve Royal Blue Soccer Polo Tee Stay Winning Long Sleeve Royal Blue Soccer Polo Tee Quick View

Stay Winning Long Sleeve Royal Blue Soccer Polo Tee

$ 19.99 $ 64.99

SIZE
COLOR
BLUE
Quantity
40% Cotton 60% Polyester Dry Fit Material Cut & Sew 2-tone fabric w/ Embroidery & Patch Designer fit (go up 1 size for a loose fit)
View Full Details

Stay Winning Long Sleeve Royal Blue Soccer Polo Tee
$ 19.99
$ 64.99
Sale
Stay Winning Anti-Hater Player's Club Maroon Scoop Tee Stay Winning Anti-Hater Player's Club Maroon Scoop Tee Quick View

Stay Winning Anti-Hater Player's Club Maroon Scoop Tee

$ 19.99 $ 24.99

SIZE
COLOR
MAROON
Quantity
The length is 2 inches longer than standard in front, 4 inches longer in the back, with a swooping scallop hemline The neckline is also more open ...
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Stay Winning Anti-Hater Player's Club Maroon Scoop Tee
$ 19.99
$ 24.99
Stay Winning SW Pin Stay Winning SW Pin Quick View

Stay Winning SW Pin

$ 9.99

Quantity
Iron stamped soft enamel lapel pin w/ sand blast Butterfly back
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Stay Winning SW Pin
$ 9.99
Stay Winning Never Losing Carty Pin Stay Winning Never Losing Carty Pin Quick View

Stay Winning Never Losing Carty Pin

$ 9.99

Green
Quantity
Iron stamped soft enamel lapel pin  Rubber back
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Stay Winning Never Losing Carty Pin
$ 9.99
Sale
Stay Winning Navy Embroidered Short Sleeve Hoodie Stay Winning Navy Embroidered Short Sleeve Hoodie Quick View

Stay Winning Navy Embroidered Short Sleeve Hoodie

$ 29.99 $ 49.99

SIZE
COLOR
BLUE
Quantity
Soft french terry pullover with drawstring hood Kangaroo pocket and short sleeves 70% Cotton 30% Polyester Construction Kangaroo Pockets Stay Winn...
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Stay Winning Navy Embroidered Short Sleeve Hoodie
$ 29.99
$ 49.99
Sold Out
Stay Winning Never Losing Pepe Black Tee Stay Winning Never Losing Pepe Black Tee Quick View

Stay Winning Never Losing Pepe Black Tee

Sold Out

SIZE
COLOR
BLACK
4.3 oz 100% Deluxe combed ringspun cotton. 50/50 Cotton Polyester Pre-shrunk to minimize shrinkage Product Description : Young Fly Frog w/ Cartie...
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Stay Winning Never Losing Pepe Black Tee
$ 19.99
$ 39.99