SALE | Stay Winning

We've slashed prices on our most popular items. This is an opportunity that shouldn't be missed to get great deals. Nothing says style quite like grabbing something great while saving some cash & that’s exactly what’s offered here. Shop our limited Stay Winning Sale items before they're gone!

  • Sort by

  • Shop by Color

  • Shop by Material

Sale
Stay Winning Embroidered Velour Maroon Hoodie Stay Winning Embroidered Velour Maroon Hoodie Quick View

Stay Winning Embroidered Velour Maroon Hoodie

$ 29.99 $ 64.99

SIZE
COLOR
MAROON
Quantity
Velvet material Gold side zippers Kangaroo pocket  Pull over  Custom drawstrings w/ gold tips Embroidered gold Stay Winning on left chest 92% poly...
View Full Details

Stay Winning Embroidered Velour Maroon Hoodie
$ 29.99
$ 64.99
Sale
Stay Winning Embroidered Velour Maroon Joggers Stay Winning Embroidered Velour Maroon Joggers Quick View

Stay Winning Embroidered Velour Maroon Joggers

$ 29.99 $ 59.99

SIZE
COLOR
MAROON
Quantity
Velvet material Custom gold tip laces Gold embroidered SW on back right pocket 92% polyester 8% spandex
View Full Details

Stay Winning Embroidered Velour Maroon Joggers
$ 29.99
$ 59.99
Sale
Stay Winning Script Black/White Camo Hoodie Stay Winning Script Black/White Camo Hoodie Quick View

Stay Winning Script Black/White Camo Hoodie

$ 39.99 $ 49.99

SIZE
COLOR
BLACK
Quantity
Custom gold tip laces Gold side zippers Hand pockets on front 80% cotton 20% polyester Made in Pakistan
View Full Details

Stay Winning Script Black/White Camo Hoodie
$ 39.99
$ 49.99
Sale
Stay Winning Embroidered Velour Blue Hoodie Stay Winning Embroidered Velour Blue Hoodie Quick View

Stay Winning Embroidered Velour Blue Hoodie

$ 29.99 $ 64.99

SIZE
COLOR
BLUE
Quantity
Velvet material Gold side zippers Kangaroo pocket  Pull over  Custom drawstrings w/ gold tips Embroidered gold Stay Winning on left chest 92% poly...
View Full Details

Stay Winning Embroidered Velour Blue Hoodie
$ 29.99
$ 64.99
Sale
Stay Winning Black/White Dad Hat Stay Winning Black/White Dad Hat Quick View

Stay Winning Black/White Dad Hat

$ 19.99 $ 29.99

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

Stay Winning Black/White Dad Hat
$ 19.99
$ 29.99
Sale
Stay Winning Embroidered Velour Blue Joggers Stay Winning Embroidered Velour Blue Joggers Quick View

Stay Winning Embroidered Velour Blue Joggers

$ 29.99 $ 59.99

SIZE
COLOR
BLUE
Quantity
Velvet material Custom gold tip laces Gold embroidered SW on back right pocket 92% polyester 8% spandex
View Full Details

Stay Winning Embroidered Velour Blue Joggers
$ 29.99
$ 59.99
Sale
Stay Winning Script Navy/White Camo Hoodie Stay Winning Script Navy/White Camo Hoodie Quick View

Stay Winning Script Navy/White Camo Hoodie

$ 39.99 $ 64.99

SIZE
COLOR
BLUE
Quantity
Custom gold tip laces Gold side zippers Hand pockets on front 80% cotton 20% polyester Made in Pakistan
View Full Details

Stay Winning Script Navy/White Camo Hoodie
$ 39.99
$ 64.99
Sale
Stay Winning Black/Red Soccer Polo Tee Stay Winning Black/Red Soccer Polo Tee Quick View

Stay Winning Black/Red Soccer Polo Tee

$ 29.99 $ 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)
View Full Details

Stay Winning Black/Red Soccer Polo Tee
$ 29.99
$ 59.99
Sale
Stay Winning Black/Navy Soccer Polo Tee Stay Winning Black/Navy Soccer Polo Tee Quick View

Stay Winning Black/Navy Soccer Polo Tee

$ 29.99 $ 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
View Full Details

Stay Winning Black/Navy Soccer Polo Tee
$ 29.99
$ 59.99
Sale
Stay Winning Script Red/White Camo Hoodie Stay Winning Script Red/White Camo Hoodie Quick View

Stay Winning Script Red/White Camo Hoodie

$ 39.99 $ 64.99

SIZE
COLOR
RED
Quantity
Custom gold tip laces Gold side zippers Hand pockets on front 80% cotton 20% polyester Made in Pakistan
View Full Details

Stay Winning Script Red/White Camo Hoodie
$ 39.99
$ 64.99
Sale
Stay Winning Yellow Gold Chain Quick View

Stay Winning Yellow Gold Chain

$ 39.99 $ 59.99

SIZE
COLOR
GOLD
Quantity
24" chain Yellow Gold Plated High grade stainless steel Exclusive Limited Edition  
View Full Details

Stay Winning Yellow Gold Chain
$ 39.99
$ 59.99
Sale
Stay Winning Red/White Dad Hat Stay Winning Red/White Dad Hat Quick View

Stay Winning Red/White Dad Hat

$ 19.99 $ 29.99

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

Stay Winning Red/White Dad Hat
$ 19.99
$ 29.99
Sale
Stay Winning Cream/Royal Soccer Polo Tee Stay Winning Cream/Royal Soccer Polo Tee Quick View

Stay Winning Cream/Royal Soccer Polo Tee

$ 29.99 $ 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)
View Full Details

Stay Winning Cream/Royal Soccer Polo Tee
$ 29.99
$ 59.99
Sold Out
Stay Winning Script Olive/White Joggers Quick View

Stay Winning Script Olive/White Joggers

Sold Out

SIZE
COLOR
GREEN
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...
View Full Details

Stay Winning Script Olive/White Joggers
$ 29.99
$ 64.99
Sale
Stay Winning Script Navy/White Joggers Quick View

Stay Winning Script Navy/White Joggers

$ 29.99 $ 64.99

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...
View Full Details

Stay Winning Script Navy/White Joggers
$ 29.99
$ 64.99
Sale
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

$ 29.99 $ 49.99

SIZE
COLOR
GREEN
Quantity
Comfort Weight Fleece 8.5 oz 80% Cotton 20% Polyester, Soft-washed Unisex
View Full Details

Stay Winning Original Logo Olive/White Crewneck Sweater
$ 29.99
$ 49.99
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  
View Full Details

Stay Winning Cartel Angel Crew Neck Sweater
$ 29.99
$ 49.99
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...
View Full Details

Stay Winning x Meet The Dealers Coast To Coast Reversible Jacket
$ 89.99
$ 159.99
Sale
Stay Winning Black/Pink Soccer Polo Tee Stay Winning Black/Pink Soccer Polo Tee Quick View

Stay Winning Black/Pink Soccer Polo Tee

$ 29.99 $ 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)
View Full Details

Stay Winning Black/Pink Soccer Polo Tee
$ 29.99
$ 59.99
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
View Full Details

Stay Winning Original Logo Navy/White Crewneck Sweater
$ 29.99
$ 54.99
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

$ 29.99 $ 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. 
View Full Details

Stay Winning Never Losing El Chapo Navy Tee
$ 29.99
$ 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
View Full Details

Stay Winning Spend Money Green Tee
$ 19.99
$ 39.99
Sale
Stay Winning Red/Navy Soccer Polo Tee Stay Winning Red/Navy Soccer Polo Tee Quick View

Stay Winning Red/Navy Soccer Polo Tee

$ 29.99 $ 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
View Full Details

Stay Winning Red/Navy Soccer Polo Tee
$ 29.99
$ 59.99
Sale
Stay Winning Punch Out Royal Blue Tee Stay Winning Punch Out Royal Blue Tee Quick View

Stay Winning Punch Out Royal Blue Tee

$ 19.99 $ 39.99

SIZE
COLOR
BLUE
Quantity
Stay Winning Punch Out Royal Blue Tee (95 PRINTED) Exclusive drop from STAY WINNING! Created by the Winners for the Winners. 100% Cotton Enzyme w...
View Full Details

Stay Winning Punch Out Royal Blue Tee
$ 19.99
$ 39.99
Sale
Stay Winning White/Navy Baseball Tee Stay Winning White/Navy Baseball Tee Quick View

Stay Winning White/Navy Baseball Tee

$ 19.99 $ 24.99

SIZE
COLOR
WHITE
Quantity
6 oz. 100% Cotton Tubular Jersey Classic Raglan fit double-needle sleeve opening and curved saddle hem Pre-shrunk to minimize shrinkage
View Full Details

Stay Winning White/Navy Baseball Tee
$ 19.99
$ 24.99
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...
View Full Details

Stay Winning Never Losing Godmother Maroon Tee
$ 19.99
$ 39.99
Sale
Stay Winning Youth Black Script Tee Quick View

Stay Winning Youth Black Script Tee

$ 19.99 $ 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...
View Full Details

Stay Winning Youth Black Script Tee
$ 19.99
$ 24.99
Sale
Stay Winning Rose Gold Chain Quick View

Stay Winning Rose Gold Chain

$ 39.99 $ 59.99

SIZE
COLOR
ROSE GOLD
Quantity
24" chain Rose Gold Plated High grade stainless steel Exclusive Limited Edition
View Full Details

Stay Winning Rose Gold Chain
$ 39.99
$ 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

$ 29.99 $ 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)
View Full Details

Stay Winning Navy/Yellow Soccer Polo Tee
$ 29.99
$ 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

$ 32.99 $ 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)
View Full Details

Stay Winning Long Sleeve Navy Blue Soccer Polo Tee
$ 32.99
$ 64.99
Sale
Stay Winning Women SW Logo Gold Embroidered Dusty Rose Joggers Quick View

Stay Winning Women SW Logo Gold Embroidered Dusty Rose Joggers

$ 29.99 $ 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...
View Full Details

Stay Winning Women SW Logo Gold Embroidered Dusty Rose Joggers
$ 29.99
$ 59.99
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...
View Full Details

Stay Winning Original Logo/Script Grey/White Varsity Jacket
$ 59.99
$ 79.99
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...
View Full Details

Stay Winning Original Logo/Script Red/White Varsity Jacket
$ 59.99
$ 79.99
Sale
Stay Winning Youth Hot Pink Script Tee Quick View

Stay Winning Youth Hot Pink Script Tee

$ 19.99 $ 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...
View Full Details

Stay Winning Youth Hot Pink Script Tee
$ 19.99
$ 24.99
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

$ 32.99 $ 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
$ 32.99
$ 64.99
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

$ 39.99 $ 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...
View Full Details

Stay Winning Women Script Logo Gold Embroidered Marled Ash Hoodie
$ 39.99
$ 64.99
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

$ 29.99 $ 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...
View Full Details

Stay Winning Women SW Logo Gold Embroidered Marled Ash Joggers
$ 29.99
$ 59.99
Sale
Stay Winning Women's Script Scoop Tee (Black) Quick View

Stay Winning Women's Script Scoop Tee (Black)

$ 19.99 $ 31.99

SIZE
COLOR
BLACK
Quantity
4.3 oz. 60/40 Combed Ring-Spun Cotton/Polyester. Soft-Washed. Ultra Soft Hand, Side-Seamed, Tightly Knit, Tapered Waist.
View Full Details

Stay Winning Women's Script Scoop Tee (Black)
$ 19.99
$ 31.99
Sale
Stay Winning Youth Grey Heather Script Tee Quick View

Stay Winning Youth Grey Heather Script Tee

$ 19.99 $ 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...
View Full Details

Stay Winning Youth Grey Heather Script Tee
$ 19.99
$ 24.99
Sale
Stay Winning Women's Script Scoop Tee (Cantaloupe) Quick View

Stay Winning Women's Script Scoop Tee (Cantaloupe)

$ 19.99 $ 31.99

SIZE
COLOR
ORANGE
Quantity
4.3 oz. 60/40 Combed Ring-Spun Cotton/Polyester. Soft-Washed. Ultra Soft Hand, Side-Seamed, Tightly Knit, Tapered Waist.
View Full Details

Stay Winning Women's Script Scoop Tee (Cantaloupe)
$ 19.99
$ 31.99
Sale
Stay Winning Youth Green Script Tee Quick View

Stay Winning Youth Green Script Tee

$ 19.99 $ 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...
View Full Details

Stay Winning Youth Green Script Tee
$ 19.99
$ 24.99
Sale
Stay Winning Women's Script Scoop Tee (Charcoal Heather) Quick View

Stay Winning Women's Script Scoop Tee (Charcoal Heather)

$ 19.99 $ 31.99

SIZE
COLOR
GREY
Quantity
4.3 oz. 60/40 Combed Ring-Spun Cotton/Polyester. Soft-Washed. Ultra Soft Hand, Side-Seamed, Tightly Knit, Tapered Waist.
View Full Details

Stay Winning Women's Script Scoop Tee (Charcoal Heather)
$ 19.99
$ 31.99
Sale
Stay Winning Pink/White Dad Hat Quick View

Stay Winning Pink/White Dad Hat

$ 19.99 $ 29.99

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

Stay Winning Pink/White Dad Hat
$ 19.99
$ 29.99
Sale
Stay Winning Navy Blue/White Dad Hat Stay Winning Navy Blue/White Dad Hat Quick View

Stay Winning Navy Blue/White Dad Hat

$ 19.99 $ 29.99

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

Stay Winning Navy Blue/White Dad Hat
$ 19.99
$ 29.99
Sale
Stay Winning Royal Blue/White Dad Hat Stay Winning Royal Blue/White Dad Hat Quick View

Stay Winning Royal Blue/White Dad Hat

$ 19.99 $ 29.99

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

Stay Winning Royal Blue/White Dad Hat
$ 19.99
$ 29.99
Sale
Stay Winning Grey/White Dad Hat Quick View

Stay Winning Grey/White Dad Hat

$ 19.99 $ 29.99

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

Stay Winning Grey/White Dad Hat
$ 19.99
$ 29.99
Sale
Stay Winning Maroon/White Dad Hat Stay Winning Maroon/White Dad Hat Quick View

Stay Winning Maroon/White Dad Hat

$ 19.99 $ 29.99

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

Stay Winning Maroon/White Dad Hat
$ 19.99
$ 29.99
Sale
Stay Winning Green/White Dad Hat Stay Winning Green/White Dad Hat Quick View

Stay Winning Green/White Dad Hat

$ 19.99 $ 29.99

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

Stay Winning Green/White Dad Hat
$ 19.99
$ 29.99