Old money

The varsity jacket, also known as a baseball, college, or letterman jacket, brings back memories of the main characters in those popular teen TV series from the ’90s. Fashion is nothing if not cyclical, and this trend, which was huge only a couple of decades ago, has made a strong comeback in recent years. Personally, I think it’s here to stay — destined to become another timeless classic. It was once championed by Lady Di, and today you’ll spot celebrities like Gigi and Bella Hadid, Kaia Gerber, Drake, and Justin Bieber rocking this ever-coveted style.

The varsity jacket first appeared in 1865, created by the Harvard baseball team. To set themselves apart, they stitched an “H” on the left side of the chest. Little did they know that, by the 1930s, the fashion world would revive the look — a revival that only grew after the release of Grease. Fun fact: Diana, Princess of Wales, made it a staple in her wardrobe, proving that varsity jackets weren’t just great for layering with basics but could also elevate more elegant outfits.

Traditionally tied to preppy style, the varsity jacket got a 21st-century update that broke all the old rules, breathing new life into fashion. Designers like Ralph Lauren and Tommy Hilfiger have repeatedly featured them in their collections, and the look quickly moved into streetwear, embraced by hip-hop artists and urban fashion. Beyond the cultural influence, the cut itself is flattering — it defines the silhouette and enhances posture, giving that sharp, stylish finish. Best of all, it’s versatile: perfect with jeans and sneakers for a laid-back vibe, or paired with tailored trousers and loafers for something smarter.

These jackets have been a fall essential for years. Made of cotton, wool, leather, or polyester, they’re perfect for chilly weather. They also look amazing oversized, styled almost like a coat. Their popularity hasn’t wavered — something that was crystal clear during Fashion Week in New York, London, Milan, Paris, and Copenhagen. Both the Autumn/Winter 2023 shows and the Spring/Summer 2024 runways highlighted varsity jackets as one of the standout street-style trends.

As for me, I’m wearing a vintage varsity jacket in bottle green and mustard — a colour combo I love. The wool body contrasts perfectly with the leather sleeves, and underneath I kept it simple with a sleeveless T-shirt tucked into high-waisted jeans. The jeans feature an asymmetrical fly with diagonally aligned buttons, giving a chic wrap effect. For a playful touch, I added red and navy striped socks with one of my favourite pairs of shoes: classic brogues printed with an Atlas map. They’re a real gem — timeless, but with a quirky twist that makes the outfit feel relaxed and modern. The gold sunglasses pick up the mustard in the jacket, while the red socks echo the pop of colour in my Mickey Mouse briefcase. I love sprinkling in a bit of childlike fun, and this green-and-red colour-block piece delivers perfectly. Finally, I threw on a navy cap to nail that ’90s American baseball-player vibe we all know and love.