• STAY WINNING BOUTIQUE
ORDER
$100+
FREE SHIPPING

NEW RELEASE "TROPHY" TEE

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

Stay Winning Never Losing Trophy Black Tee

$ 35.99

Size
Quantity
Stay Winning Never Losing Trophy Tee Exclusive drop from STAY WINNING! Created by the Winners for the Winners. 100% Cotton Enzyme wash for an ultr...
Stay Winning Never Losing Trophy Yellow Tee Stay Winning Never Losing Trophy Yellow Tee Quick View

Stay Winning Never Losing Trophy Yellow Tee

$ 35.99

Size
Quantity
Stay Winning Never Losing Trophy Tee Exclusive drop from STAY WINNING! Created by the Winners for the Winners. 100% Cotton Enzyme wash for an ultr...
Stay Winning Rising Sun Navy Tee Stay Winning Rising Sun Navy Tee Quick View

Stay Winning Rising Sun Navy Tee

$ 34.99

Size
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...
Stay Winning Rising Sun Coral Tee Stay Winning Rising Sun Coral Tee Quick View

Stay Winning Rising Sun Coral Tee

$ 34.99

Size
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...
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

$ 34.99

Size
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. ...
Stay Winning Spend Money Green Tee Stay Winning Spend Money Green Tee Quick View

Stay Winning Spend Money Green Tee

$ 31.99

Size
Quantity
Stay Winning Spend Money Green Tee 5.5 oz 100% Combed Ringspun Cotton
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

$ 31.99

Size
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 yo...
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

$ 31.99

Size
Quantity
Stay Winning Hyphy By Nature Navy/Red Tee Crafted in a modern cut that sits on the body for a clean silhouette, soft lightweight fabric has you ...
Stay Winning Family Over Everything Escobar Black Tee Stay Winning Family Over Everything Escobar Black Tee Quick View

Stay Winning Family Over Everything Escobar Black Tee

$ 31.99

Size
Color
BLACK
Quantity
Stay Winning Family Over Everything Escobar Black Tee 5.5 oz 100% Combed Ringspun Cotton
Stay Winning Family Over Everything Godfather Black Tee Stay Winning Family Over Everything Godfather Black Tee Quick View

Stay Winning Family Over Everything Godfather Black Tee

$ 31.99

Size
Color
BLACK
Quantity
Stay Winning Family Over Everything Godfather Black Tee 5.5 oz 100% Combed Ringspun Cotton
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

$ 34.99

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

Stay Winning Never Losing Godmother Maroon Tee

$ 34.99

Size
Quantity
Fine Knit  4.3 oz 100% Ringspun Cotton Exclusive limited print Product Description : Griselda Blanco de Medellin, Columbia w/ Charles Cosby of Eas...
Stay Winning Double Dragon Black Tee Stay Winning Double Dragon Black Tee Quick View

Stay Winning Double Dragon Black Tee

$ 34.99

Size
Quantity
Stay Winning Double Dragon Black Tee Crafted in a modern cut that sits on the body for a clean silhouette, soft lightweight fabric has you covere...
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

$ 99.99

Size
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...
Stay Winning Original Logo/Script Gray/White Varsity Jacket Stay Winning Original Logo/Script Gray/White Varsity Jacket Quick View

Stay Winning Original Logo/Script Gray/White Varsity Jacket

$ 99.99

Size
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...
Stay Winning Original Logo/Script Black/White Varsity Jacket Stay Winning Original Logo/Script Black/White Varsity Jacket Quick View

Stay Winning Original Logo/Script Black/White Varsity Jacket

$ 99.99

Size
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...
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

$ 99.99

Size
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...
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

$ 99.99

Size
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...
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

$ 49.99

Size
Quantity
Stay Winning Original Logo Olive/White Crewneck Sweater Comfort Weight Fleece 8.5 oz 80% Cotton 20% Polyester, Soft-washed Unisex
Stay Winning Script Olive/White Joggers Quick View

Stay Winning Script Olive/White Joggers

$ 59.99

Size
Quantity
Stay Winning Script Olive/White Joggers 8.5 oz Soft-washed 80/20 Cotton Poly Fleece Side slash pockets and back right pocket Crotch gusset f...
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

$ 49.99

Size
Quantity
Stay Winning Original Logo Navy/White Crewneck Sweater Comfort Weight Fleece 8.5 oz 80% Cotton 20% Polyester, Soft-washed Unisex
Stay Winning Script Navy/White Joggers Quick View

Stay Winning Script Navy/White Joggers

$ 59.99

Size
Quantity
Stay Winning Script Navy/White Joggers 8.5 oz Soft-washed 80/20 Cotton Poly Fleece Side slash pockets and back right pocket Crotch gusset fo...
Stay Winning Original Logo Red/White Crewneck Sweater Stay Winning Original Logo Red/White Crewneck Sweater Quick View

Stay Winning Original Logo Red/White Crewneck Sweater

$ 49.99

Size
Quantity
Stay Winning Original Logo Red/White Crewneck Sweater Comfort Weight Fleece 8.5 oz 80% Cotton 20% Polyester, Soft-washed Unisex
Stay Winning Script Red/White Joggers Quick View

Stay Winning Script Red/White Joggers

$ 59.99

Size
Quantity
Stay Winning Script Red/White Joggers 8.5 oz Soft-washed 80/20 Cotton Poly Fleece Side slash pockets and back right pocket Crotch gusset for...
Stay Winning Original Logo Black/White Crewneck Sweater Stay Winning Original Logo Black/White Crewneck Sweater Quick View

Stay Winning Original Logo Black/White Crewneck Sweater

$ 49.99

Size
Quantity
Stay Winning Original Logo Black/White Crewneck Sweater Comfort Weight Fleece 8.5 oz 80% Cotton 20% Polyester, Soft-washed Unisex
Stay Winning Script Black/White Joggers Quick View

Stay Winning Script Black/White Joggers

$ 59.99

Size
Quantity
Stay Winning Script Black/White Joggers 8.5 oz Soft-washed 80/20 Cotton Poly Fleece Side slash pockets and back right pocket Crotch gusset f...
Stay Winning Script Navy/White Camo Hoodie Stay Winning Script Navy/White Camo Hoodie Quick View

Stay Winning Script Navy/White Camo Hoodie

$ 64.99

Size
Quantity
Stay Winning Script Navy/White Camo Hoodie Custom gold tip laces Gold side zippers Hand pockets on front 80% cotton 20% polyester Made in Pakistan
Stay Winning Script Black/White Camo Hoodie Stay Winning Script Black/White Camo Hoodie Quick View

Stay Winning Script Black/White Camo Hoodie

$ 64.99

Size
Quantity
Stay Winning Original Script Black Camo Hoodie Custom gold tip laces Gold side zippers Hand pockets on front 80% cotton 20% polyester Made in Paki...
Stay Winning Script Red/White Camo Hoodie Stay Winning Script Red/White Camo Hoodie Quick View

Stay Winning Script Red/White Camo Hoodie

$ 64.99

Size
Quantity
Stay Winning Script Red/White Camo Hoodie Custom gold tip laces Gold side zippers Hand pockets on front 80% cotton 20% polyester Made in Pakistan
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

$ 159.99

Size
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...
Stay Winning Olive Crop Top Hoodie Quick View

Stay Winning Olive Crop Top Hoodie

$ 47.99

Size
Quantity
7.8 Ounce Cotton Fleece Oversized Look + Crop Top Heavy Weight Fit
Stay Winning Gray Crop Top Hoodie Quick View

Stay Winning Gray Crop Top Hoodie

$ 47.99

Size
Quantity
7.8 Ounce Cotton Fleece Oversized Look + Crop Top Heavyweight Fit
Stay Winning Black Crop Top Hoodie Quick View

Stay Winning Black Crop Top Hoodie

$ 47.99

Size
Quantity
7.8 Ounce Cotton Fleece Oversized Look + Crop Top Heavyweight Fit
Stay Winning Red Crop Top Hoodie Quick View

Stay Winning Red Crop Top Hoodie

$ 47.99

Size
Quantity
7.8 Ounce Cotton Fleece Oversized Look + Crop Top Heavyweight Fit
Stay Winning Embroidered Velour Black Hoodie Stay Winning Embroidered Velour Black Hoodie Quick View

Stay Winning Embroidered Velour Black Hoodie

$ 64.99

Size
Quantity
Velvet material Gold side zippers Kangaroo pocket  Pull over  Custom drawstrings w/ gold tips Embroidered gold Stay Winning on left chest 92% Poly...
Stay Winning Embroidered Velour Black Joggers Stay Winning Embroidered Velour Black Joggers Quick View

Stay Winning Embroidered Velour Black Joggers

$ 59.99

Size
Quantity
Velvet material Custom gold tip laces Gold embroidered SW on back right pocket 92% polyester 8% spandex
Stay Winning White/Black Snap Back Stay Winning White/Black Snap Back Quick View

Stay Winning White/Black Snap Back

$ 34.99

Quantity
Comes with an exclusive Stay Winning Gold Pin 80% Acrylic / 20% Wool (60% Cotton / 40% Polyester) Classic shape Premium wool blend Matching plasti...
Stay Winning Green/White Snap Back Stay Winning Green/White Snap Back Quick View

Stay Winning Green/White Snap Back

$ 34.99

Quantity
Comes with an exclusive gold Stay Winning Pin 80% Acrylic / 20% Wool (60% Cotton / 40% Polyester) Classic shape Premium wool blend Matching plasti...
Stay Winning Green/Gold Snap Back Stay Winning Green/Gold Snap Back Quick View

Stay Winning Green/Gold Snap Back

$ 34.99

Quantity
Comes with an exclusive gold Stay Winning Pin 80% Acrylic / 20% Wool (60% Cotton / 40% Polyester) Classic shape Premium wool blend Matching plasti...
Stay Winning Royal/White Snap Back Stay Winning Royal/White Snap Back Quick View

Stay Winning Royal/White Snap Back

$ 34.99

Quantity
Comes with an exclusive Stay Winning Gold Pin 80% Acrylic / 20% Wool (60% Cotton / 40% Polyester) Classic shape Premium wool blend Matching plasti...
Stay Winning Royal/Gold Snap Back Stay Winning Royal/Gold Snap Back Quick View

Stay Winning Royal/Gold Snap Back

$ 34.99

Quantity
Comes with an exclusive Stay Winning Gold Pin 80% Acrylic / 20% Wool (60% Cotton / 40% Polyester) Classic shape Premium wool blend Matching plasti...
Stay Winning Black/White Snap Back Hat Stay Winning Black/White Snap Back Hat Quick View

Stay Winning Black/White Snap Back Hat

$ 34.99

Quantity
Comes with an exclusive Gold Pin 80% Acrylic / 20% Wool (60% Cotton / 40% Polyester) Classic shape Premium wool blend Matching plastic snap Classi...
Stay Winning Black/Blue Snap Back Hat Stay Winning Black/Blue Snap Back Hat Quick View

Stay Winning Black/Blue Snap Back Hat

$ 34.99

Quantity
Comes with an exclusive Gold Stay Winning Pin 80% Acrylic / 20% Wool (60% Cotton / 40% Polyester) Classic shape Premium wool blend Matching plasti...
Stay Winning Black/Gold Snap Back Hat Stay Winning Black/Gold Snap Back Hat Quick View

Stay Winning Black/Gold Snap Back Hat

$ 34.99

Quantity
Comes with an exclusive Gold Stay Winning Pin 80% Acrylic / 20% Wool (60% Cotton / 40% Polyester) Classic shape Premium wool blend Matching plasti...
Stay Winning Black/Red Snap Back Hat Stay Winning Black/Red Snap Back Hat Quick View

Stay Winning Black/Red Snap Back Hat

$ 34.99

Quantity
Comes with an exclusive Stay Winning Pin 80% Acrylic / 20% Wool (60% Cotton / 40% Polyester) Classic shape Premium wool blend Matching plastic sna...
Stay Winning Maroon/White Snap Back Hat Stay Winning Maroon/White Snap Back Hat Quick View

Stay Winning Maroon/White Snap Back Hat

$ 34.99

Quantity
Comes with an exclusive Gold Stay Winning Pin Contents: 80% acrylic / 20% wool (60% cotton / 40% polyester) Classic shape Premium wool blend Class...
Stay Winning Maroon/Gold Snap Back Hat Stay Winning Maroon/Gold Snap Back Hat Quick View

Stay Winning Maroon/Gold Snap Back Hat

$ 34.99

Quantity
Comes with an exclusive Gold Stay Winning Pin Contents: 80% acrylic / 20% wool (60% cotton / 40% polyester) Classic shape Premium wool blend Class...
Stay Winning Red/Gold Snap Back Stay Winning Red/Gold Snap Back Quick View

Stay Winning Red/Gold Snap Back

$ 34.99

Quantity
Comes with an exclusive Stay Winning Gold Pin 80% Acrylic / 20% Wool (60% Cotton / 40% Polyester) Classic shape Premium wool blend Matching plasti...

S W N L

Follow @staywinningboutique On Instagram

Join Our Mailing List