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It’s time to champion a look that’s effortless and timeless. The varsity jacket’s logo-emblazoned crests have been a staple for preps and sporty types for decades. This week, I’m getting you clued up on how this all-American classic bomber can lift your styling game.

LEFT: BASEBALL JACKET WITH PATCHES, SHOP NOW, SILK MONOGRAM PAJAMA SHORTS, SHOP NOW, SILHOUETTE ANKLE BOOTS, SHOP NOW, LOUIS VUITTON. RIGHT: PALOMA S MEDIUM BAG, CHRISTIAN LOUBOUTIN, SHOP NOW 

LOOK ONE

To date every designer has made their own iteration, from Louis Vuitton (as seen above), to Tommy Hilfiger and Thom Browne. But did you know the first letterman jacket actually dates back to 1865, and with strict rules: Harvard baseball athletes got to wear the iconic jacket to represent how well they played and air a level of athleticism or “jock” as we all know it. Athletes kept the jacket for the season, but if they were “benched”, the jacket was returned. Nothing like a bit of competition. These days anyone can wear a letterman jacket; streetwear sultanas, sporty types, fashion fanatics.

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LOOK TWO

One of my favourite letterman jackets is the Celine’s version, where designer Hedi Slimane created the calculated thrown-together vibe, layering a hoodie under the varsity bomber with a subtle ripped jean and prepster appeal. Consider a tee or tank for warmer months. Or if you’re going from the gym to the cafe, opt for an unbuttoned white shirt with bike shorts. It’s ideal light layering.

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LOOK THREE

Oversize still rules. Whether it’s a cable knit, crew sweatshirt or beefy-T (As an American, I can tell you this term is American for heavy weight t-shirt], they tend to hold their shape better. A pleated skirt like this one by Max Mara adds a sophisticated take without losing street cred. By the way, no one is more clever than Loewe when it comes to accessories telling a story. This woven pocket pouch is perfect for holding the absolute essentials whether you’re going from the pool to the bar or gazing at the sunset…smartphone tucked away.

LEFT: CREPE SATIN SHIRT, SHOP NOW, WOOL SHORTS, SHOP NOW, FENDI. RIGHT: DYLAN FLARED JEANS IN SUNSET WASH DENIM, SHOP NOW, CT-02 MID SNEAKER WITH SCRATCH IN CALFSKIN, SHOP NOW, AVA BAG IN TRIOMPHE CANVAS & CALFSKIN, SHOP NOW, CELINE

LOOK FOUR & FIVE

The preppy vibe would be lost without a Bermuda short, or dial in a sexier look with this high waisted pleated version and cropped shirting as seen here from Fendi. For those who like everything oversized, choose your jeans one size larger and cinch in at the waist with a belt.

Photography: Sean Slattery
Fashion Director: Aileen Marr
Hair & Makeup: Desiree Wise
Model: Narah Baptista / Chic

SHOP OUR FAVOURITE BOMBER JACKETS:

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FRAME X RITZ PARIS, RITZ VARSITY JACKET, $3,748, SHOP NOW
TOMMYXTIMBERLAND, DUAL GENDER REVERSIBLE VARSITY JACKET, $899, SHOP NOW
AIMÉ LEON DORE, CHESS CLUB VARSITY JACKET, $1,950, SHOP NOW
STADIUM GOODS, STADIUM VARSITY LETTERMAN JACKET, $769, SHOP NOW