CHESTER'S SMILE IS A SMALL, DESIGN-LED BRAND BASED IN TORONTO, CANADA.

EVERY PIECE WE RELEASE STARTS WITH A STORY, NOT A TREND, NOT A GRAPHIC DROPPED ONTO COTTON.

WE DESIGN AROUND MOMENTS THAT STICK: SOUNDTRACK ERAS, CULTURAL SHIFTS, SPORTS RUNS, SCENES FROM LIFE THAT DON'T FADE.

EVERY DROP IS PRODUCED IN LIMITED QUANTITIES. NO RESTOCKS. NO RE-RUNS.

WHEN A PIECE IS GONE, IT'S ARCHIVED FOR GOOD.

OUR GRAPHICS DON'T START AS IMAGES. THEY START AS IDEAS, A FEELING, A MEMORY, A MOMENT WORTH HOLDING ONTO.

EACH DESIGN IS BUILT WITH INTENT. LAYERS, REFERENCES, AND DETAILS THAT ONLY REVEAL THEMSELVES WHEN YOU LOOK CLOSER.

THERE ARE EASTER EGGS IN ALMOST EVERY PIECE. COLORS PULLED FROM ERAS. NUMBERS THAT MEAN SOMETHING. REFERENCES THAT ONLY CLICK IF YOU KNOW.

THIS ISN'T FAST FASHION. IT'S SLOW, CONSIDERED DESIGN.

CHESTER'S SMILE IS DESIGNED AND LED BY HASSAN YAHYA.

A TORONTO NATIVE WHO SPENT YEARS IN SOUTHERN CALIFORNIA, SPLITTING TIME BETWEEN LOS ANGELES AND SAN DIEGO; WORKING WITH HIP-HOP ARTISTS, DESIGNERS, AND STREETWEAR TEAMS ON GRAPHICS, MERCH, AND FULL CLOTHING LINES.

THAT ERA SHAPED EVERYTHING: THE OVERSIZED FITS. THE VINTAGE REFERENCES. THE IDEA THAT A SHIRT COULD FEEL LIKE A MEMORY, NOT JUST CLOTHING.

WHEN HE MOVED BACK TO TORONTO, THAT PHILOSOPHY CAME WITH HIM.

SMALL RUNS. REAL MEANING. NOTHING WATERED DOWN.

OUR TEES ARE MADE USING 8OZ, 100% COTTON BLANKS SOURCED FROM PREMIUM MILLS IN PORTUGAL.

WE TESTED EVERYTHING. DIFFERENT SUPPLIERS, DIFFERENT WEIGHTS, DIFFERENT FINISHES.

SOME LOOKED GOOD ON DAY ONE AND LOST THEIR SHAPE. SOME FELT ROUGH. SOME DIDN'T HOLD UP AFTER A FEW WASHES.

THE PORTUGUESE COTTON DID. SOFT BUT STRUCTURED. SUBSTANTIAL WITHOUT FEELING STIFF. BUILT TO WEAR IN, NOT FALL APART.

EVERY DESIGN IS PRINTED WITH THE SAME STANDARD. BUILT TO LAST, NOT TO FLIP.

OUR FIT IS OVERSIZED WITH A STANDARD LENGTH. NOT CROPPED. NOT TOO LONG.

DESIGNED TO DRAPE PROPERLY AND AGE WELL OVER TIME.

IF YOU PREFER A RELAXED FIT, TAKE YOUR USUAL SIZE.

IF YOU'RE BETWEEN SIZES, SIZE UP.

EVERY PIECE IS PRODUCED IN SMALL BATCHES AFTER ORDERS ARE PLACED.

PRODUCTION TAKES APPROXIMATELY TWO WEEKS.

SHIPPING TAKES AN ADDITIONAL ONE TO TWO WEEKS, DEPENDING ON YOUR LOCATION RELATIVE TO TORONTO.

TRACKING IS SENT AS SOON AS YOUR ORDER SHIPS. UPDATES ARE ALWAYS SHARED ALONG THE WAY.

THIS IS INTENTIONAL PRODUCTION, NOT RUSHED FULFILLMENT.