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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Stay Winning Royal Blue Sweats Stay Winning Royal Blue Sweats Quick View

Stay Winning Royal Blue Sweats

$ 44.99

Size
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

$ 64.99

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

$ 64.99

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

Stay Winning Cork Popper Gang Snapback Hat

$ 44.99

Quantity
5-panel snapback Mesh back panels Wool front panels Fully embroidered w/ chenille
Stay Winning Red Messenger Bag Quick View

Stay Winning Red Messenger Bag

$ 19.99

Quantity
100% Cotton Canvas 13"W x 13"H 
Stay Winning Royal Blue Messenger Bag Quick View

Stay Winning Royal Blue Messenger Bag

$ 19.99

Quantity
100% Cotton Canvas 13"W x 13"H 
Stay Winning Navy Blue Messenger Bag Quick View

Stay Winning Navy Blue Messenger Bag

$ 19.99

Quantity
100% Cotton Canvas 13"W x 13"H 
Stay Winning Black Messenger Bag Quick View

Stay Winning Black Messenger Bag

$ 19.99

Quantity
100% Cotton Canvas 13"W x 13"H 
Stay Winning Camo Mesh Shorts Stay Winning Camo Mesh Shorts Quick View

Stay Winning Camo Mesh Shorts

$ 59.99

Size
Quantity
3 zipper pockets Fully embroidered Inside drawstrings Polyester mesh material
Stay Winning Vintage Wash Logo Charcoal Tee Stay Winning Vintage Wash Logo Charcoal Tee Quick View

Stay Winning Vintage Wash Logo Charcoal Tee

$ 44.99

Size
Quantity
100% cotton Pre-shrunk Vintage wash
Stay Winning SW Black Snapback Hat Stay Winning SW Black Snapback Hat Quick View

Stay Winning SW Black Snapback Hat

$ 44.99

BLACK
Quantity
6 panel wool snap back Puff embroidery Black strap 
Stay Winning Black Snapback Hat Stay Winning Black Snapback Hat Quick View

Stay Winning Black Snapback Hat

$ 44.99

BLACK
Quantity
6 panel wool snap back Puff embroidery Black strap 
PEMDAS EMPIRE presents PEMD4S C-Roc x Tanibal (Full Album CD 2020) PEMDAS EMPIRE presents PEMD4S C-Roc x Tanibal (Full Album CD 2020) Quick View

PEMDAS EMPIRE presents PEMD4S C-Roc x Tanibal (Full Album CD 2020)

$ 19.99

RED
Quantity
IT'S WHATEVER LIFE ON THE LINE TALK TO ME  BETTER LIFE featuring Benny & DT1910 GORILLA GOOK  SKEMIN' featuring Gee Q Pham  MAJOR STR...
CSTEROC presents GOOK MOBB MUZIK (Double Disc CD 2014) CSTEROC presents GOOK MOBB MUZIK (Double Disc CD 2014) Quick View

CSTEROC presents GOOK MOBB MUZIK (Double Disc CD 2014)

$ 39.99

BLACK
Quantity
AIR MAX HOME RUN featuring Tanibal & D$ FRENCH WATER GANGSTA SHIT featuring Spice 1 O.G. HUSTLE  ROYAL BLUE featuring Too Sicc NINJA COP ...
CSTEROC - Stay Winning (Full Album CD 2011) CSTEROC - Stay Winning (Full Album CD 2011) Quick View

CSTEROC - Stay Winning (Full Album CD 2011)

$ 9.99

TEAL
Quantity
BRAIN FULLA GAME THE ONLY THING featuring Voodoo, Skitz & Matt Blaque D-BOY BLUEZ  SUN BLOCK featuring Skitz  GAME TIGHT PULL THE PLUG ...
CSTEROC  - Gamblin' & Grindin' (Full Album CD 2005) CSTEROC  - Gamblin' & Grindin' (Full Album CD 2005) Quick View

CSTEROC - Gamblin' & Grindin' (Full Album CD 2005)

$ 14.99

RED
Quantity
YA NEVA MET COME UPS FAMILY OVER SCRILL produced by Aliaz (Portland) GET MY CASH ON featuring Keek Dogg (Newark) LIGHT BROWN DO YOU REMEMBER? GO...
CSTEROC - In The East Bay (Full Album CD 2003) CSTEROC - In The East Bay (Full Album CD 2003) Quick View

CSTEROC - In The East Bay (Full Album CD 2003)

$ 14.99

GREEN
Quantity
IN THE EAST BAY VERSES featuring Tonestone & G-Bless BY THE HUB BE YOURSELF (Fremont x Oakland) AMERICA (1st music video)  DIME PIECE MR....
Young Csteroc laces you wit... REALITY RAPS (Compilation Album CD 2003) Young Csteroc laces you wit... REALITY RAPS (Compilation Album CD 2003) Quick View

Young Csteroc laces you wit... REALITY RAPS (Compilation Album CD 2003)

$ 39.99

YELLOW
Quantity
WAR TIME - Skitz WHAT YOU THINK? - R.E.G. ROGUE LIFE - Skitz FRAUDULENT - Millanina 510 CLICK - SDFB NEVA SOBER - Sidewayz YOUNG VIETNAMESE ...
Lil' C'Ster - Young Viet Vet (EP Cassette Tape 1998) Lil' C'Ster - Young Viet Vet (EP Cassette Tape 1998) Quick View

Lil' C'Ster - Young Viet Vet (EP Cassette Tape 1998)

$ 999.99

BLACK
Quantity
SIDE A : Mr. Cster (3:15)  Sicc Manish Wicced (5:22)  415-510 (6:22) SIDE B : Gettin' Faded (3:18)  On A Mission (4:10)  Street Poetry (7:40) Recor...
Stay Winning French Water Pin Stay Winning French Water Pin Quick View

Stay Winning French Water Pin

$ 9.99

Quantity
Iron stamped soft enamel lapel pin  Rubber back
Stay Winning Sports Pin Stay Winning Sports Pin Quick View

Stay Winning Sports Pin

$ 9.99

BLACK
Quantity
Silkscreen print die cut lapel pin Rubber back

Stay Winning Sports Pin

$ 9.99
Stay Winning Gold Script Pin Stay Winning Gold Script Pin Quick View

Stay Winning Gold Script Pin

$ 9.99

GOLD
Quantity
Iron stamped soft enamel lapel pin w/ sand blast Rubber back
Stay Winning Neon Button Stay Winning Neon Button Quick View

Stay Winning Neon Button

$ 9.99

BLACK
Quantity
- Screenprint button

Stay Winning Neon Button

$ 9.99
Stay Winning Bubbas Pin Stay Winning Bubbas Pin Quick View

Stay Winning Bubbas Pin

$ 9.99

Quantity
Iron stamped soft enamel lapel pin  Rubber back

Stay Winning Bubbas Pin

$ 9.99
Stay Winning Americano Pin Stay Winning Americano Pin Quick View

Stay Winning Americano Pin

$ 9.99

WHITE
Quantity
Iron stamped soft enamel lapel pin  Rubber back
Stay Winning Loudy Bo Hoodie Stay Winning Loudy Bo Hoodie Quick View

Stay Winning Loudy Bo Hoodie

$ 64.99

Size
Quantity
10.5 oz 80% cotton/20% polyester Double lined hood
Stay Winning Loudy Bo Tee Stay Winning Loudy Bo Tee Quick View

Stay Winning Loudy Bo Tee

$ 39.99

Size
Quantity
6 oz 100% cotton Preshrunk

Stay Winning Loudy Bo Tee

$ 39.99
Stay Winning Maroon Flare Sweatpants Stay Winning Maroon Flare Sweatpants Quick View

Stay Winning Maroon Flare Sweatpants

$ 49.99

SIZE
COLOR
MAROON
Quantity
100% cotton Screen printing 320 GSM / 9.44 oz Back zipper pocket Side zipper pockets Pre-shrunk for minimum shrinkage
Stay Winning SW Stay Winning Maroon Hoodie Stay Winning SW Stay Winning Maroon Hoodie Quick View

Stay Winning SW Stay Winning Maroon Hoodie

$ 64.99

SIZE
COLOR
MAROON
Quantity
100% cotton Screen printing 320 GSM / 9.44 oz Pre-shrunk for minimum shrinkage
Stay Winning Black Sweatpants Stay Winning Black Sweatpants Quick View

Stay Winning Black Sweatpants

$ 49.99

SIZE
COLOR
BLACK
Quantity
100% cotton Screen printing 320 GSM / 9.44 oz Back zipper pocket Side zipper pockets Pre-shrunk for minimum shrinkage
Sold Out
Stay Winning SW Stay Winning Black Hoodie Stay Winning SW Stay Winning Black Hoodie Quick View

Stay Winning SW Stay Winning Black Hoodie

Sold Out

SIZE
COLOR
BLACK
100% cotton Screen printing 320 GSM / 9.44 oz Pre-shrunk for minimum shrinkage
Stay Winning x Loudy Bo Snapback Hat Stay Winning x Loudy Bo Snapback Hat Quick View

Stay Winning x Loudy Bo Snapback Hat

$ 44.99

SIZE
COLOR
BLACK
Quantity
Stay Winning x Loudy Bo 5-panel snap back Mesh back panels Wool front panels Fully embroidered Yellow back strap
Stay Winning x Wrldclo Snapback Hat Stay Winning x Wrldclo Snapback Hat Quick View

Stay Winning x Wrldclo Snapback Hat

$ 44.99

SIZE
COLOR
BLACK
Quantity
Stay Winning x Wrldclo Black strap Curved bill Premium wool  Fully embroidered
Stay Winning Kasino Trucker Hat Stay Winning Kasino Trucker Hat Quick View

Stay Winning Kasino Trucker Hat

$ 24.99

SIZE
COLOR
BLACK
Quantity
Embroidered Last Kickz hat ever (Stay Winning x Kickz) White back strap Foam / Mesh Trucker
Stay Winning Kasino Hoodie Stay Winning Kasino Hoodie Quick View

Stay Winning Kasino Hoodie

$ 64.99

SIZE
COLOR
BLACK
Quantity
Unisex Made in U.S.A Mid-Weight French Terry 100% Cotton

Stay Winning Kasino Hoodie

$ 64.99
Stay Winning Faded Teal Embroidered Joggers Stay Winning Faded Teal Embroidered Joggers Quick View

Stay Winning Faded Teal Embroidered Joggers

$ 59.99

SIZE
COLOR
TEAL
Quantity
Regular fit Mid-weight, 8.5 oz 80% cotton 20% polyester anti-pill fleece Self-fabric elasticated waistband & hem cuffs, 2 side pockets, single ...
Stay Winning Faded Teal Embroidered Hoodie Stay Winning Faded Teal Embroidered Hoodie Quick View

Stay Winning Faded Teal Embroidered Hoodie

$ 64.99

SIZE
COLOR
TEAL
Quantity
Regular fit Mid weight, 8.5 oz 80% cotton 20% polyester anti-pill fleece Pullover hood, raglan sleeves, kangaroo pocket, lined hood, tonal flat dra...
Stay Winning Faded Blue Embroidered Joggers Stay Winning Faded Blue Embroidered Joggers Quick View

Stay Winning Faded Blue Embroidered Joggers

$ 59.99

SIZE
COLOR
BLUE
Quantity
Regular fit Mid-weight, 8.5 oz 80% cotton 20% polyester anti-pill fleece Self-fabric elasticated waistband & hem cuffs, 2 side pockets, single ...
Stay Winning Faded Blue Embroidered Hoodie Stay Winning Faded Blue Embroidered Hoodie Quick View

Stay Winning Faded Blue Embroidered Hoodie

$ 64.99

SIZE
COLOR
BLUE
Quantity
Regular fit Mid weight, 8.5 oz 80% cotton 20% polyester anti-pill fleece Pullover hood, raglan sleeves, kangaroo pocket, lined hood, tonal flat dra...
Stay Winning Faded Black Embroidered Joggers Stay Winning Faded Black Embroidered Joggers Quick View

Stay Winning Faded Black Embroidered Joggers

$ 59.99

SIZE
COLOR
BLACK
Quantity
Regular fit Mid-weight, 8.5 oz 80% cotton 20% polyester anti-pill fleece Self-fabric elasticated waistband & hem cuffs, 2 side pockets, single ...
Stay Winning Faded Black Embroidered Hoodie Stay Winning Faded Black Embroidered Hoodie Quick View

Stay Winning Faded Black Embroidered Hoodie

$ 64.99

SIZE
COLOR
BLACK
Quantity
Regular fit Mid weight, 8.5 oz 80% cotton 20% polyester anti-pill fleece Pullover hood, raglan sleeves, kangaroo pocket, lined hood, tonal flat dra...
Stay Winning Carty The Frog Trucker Hat Stay Winning Carty The Frog Trucker Hat Quick View

Stay Winning Carty The Frog Trucker Hat

$ 44.99

Royal Blue
Quantity
5 panel Chenille/Embrodery Adjustable snapback Foam/Mesh Trucker Hat
Stay Winning Green Floral Jacket Hoodie Stay Winning Green Floral Jacket Hoodie Quick View

Stay Winning Green Floral Jacket Hoodie

$ 79.99

Size
Color
Green
Quantity
100% cotton Hoodie Jacket Zippers & buttons Inside polyester linen Floral design w/ SW logos
Stay Winning Maroon Floral Jacket Hoodie Stay Winning Maroon Floral Jacket Hoodie Quick View

Stay Winning Maroon Floral Jacket Hoodie

$ 79.99

Size
Color
Maroon
Quantity
100% cotton Hoodie Jacket Zippers & buttons Inside polyester linen Floral design w/ SW logos
Stay Winning Talent Black Tee Stay Winning Talent Black Tee Quick View

Stay Winning Talent Black Tee

$ 39.99

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

Stay Winning Talent White Tee

$ 39.99

SIZE
COLOR
WHITE
Quantity
100% Cotton. Pre-shrunk material. For best results machine wash inside out warm, hang dry & iron inside out.
Stay Winning GOAT Trophy Black Tee Stay Winning GOAT Trophy Black Tee Quick View

Stay Winning GOAT Trophy Black Tee

$ 39.99

SIZE
COLOR
BLACK
Quantity
100% Cotton. Pre-shrunk material. For best results machine wash inside out warm, hang dry & iron inside out.
Stay Winning My Other Brother White Tee Stay Winning My Other Brother White Tee Quick View

Stay Winning My Other Brother White Tee

$ 39.99

SIZE
COLOR
WHITE
Quantity
100% Cotton. Pre-shrunk material. For best results machine wash inside out warm, hang dry & iron inside out.