In the 1820s, rowers at the Lady Margaret Boat Club of St. John’s College wore bright red flannel jackets. They were loose-fitting, unstructured, and made to keep athletes warm on the river. Their vivid color earned them the nickname “blazers,” and the name stuck.

A few decades later, the British Royal Navy adopted the idea—refining it into something darker, more structured, and more formal. Navy wool. Brass buttons. Double-breasted front. Still relaxed enough for life at sea, but sharp enough for officers receiving guests or heading ashore. That’s the version most people think of when they hear “blazer” today.

From there, the blazer spread. British schools and clubs adopted striped versions to signal team allegiance. Ivy League campuses turned it into a preppy essential. Hollywood stars like Cary Grant and Paul Newman gave it elegance and edge. By the 1980s and ’90s, Giorgio Armani reimagined it entirely—softening the shape, relaxing the shoulder, and showing us that tailoring didn’t have to be stiff to be smart.

Today, the blazer continues to evolve. It’s worn over T-shirts, hoodies, polos, and ties. It’s been cropped, deconstructed, oversized, and minimalized. But the essence remains: a jacket with structure and ease, history and range. A tailored piece that doesn’t box you in.

At Tailors’ Keep, we’re interested in garments that carry history but aren’t trapped by it. Here are three new takes on the blazer, each nodding to its heritage—while speaking to how we wear it now:

The navy blazer has long signaled polish, tradition, and conformity. It’s the uniform of prep schools, country clubs, and corporate lobbies. But that’s precisely what made it such a powerful tool for subversion.

Style icons like Miles Davis and Andy Warhol understood the code—and then rewrote it from the inside. Davis wore his blazers with controlled nonchalance, pairing gold buttons with slim trousers and attitude, reinventing Ivy style for the cool jazz era. Warhol, ever the provocateur, wore his like armor: clean on the outside, chaos beneath the surface.

The blazer gave them access to the room—but then they gave the room the finger. That’s the beauty of the garment: it can signal belonging or rebellion, depending entirely on how you wear it.

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