The pilotka hat—also known as the garrison cap, flight cap, or side cap—started out as purely practical military headwear in the early 20th century, most famously worn by the Soviet Red Army. Over time, it’s quietly found its way into fashion. It’s still very much a niche piece, but that’s part of the appeal. The pilotka has a strong sense of character, thanks to its clear military roots and clean, structured shape. You do see it pop up occasionally in designer collections. Giorgio Armani, for example, has often looked to military clothing for inspiration because of its functionality and sharp lines, and side caps have appeared in his collections over the years. What makes the pilotka so interesting is its simplicity. It folds flat, sits neatly on the head, and manages to carry a lot of history without being showy. Traditionally, it’s worn slightly tilted to the right, with the lower edge just above the right ear and the badge or star centred on the forehead. It should fit snugly, with a gentle pinch at the front and back to keep its shape.
The pilotka was originally designed out of
necessity. Its name comes from the Russian word for pilot, as it was first
introduced in 1913 for military aviators. During the Soviet era, it became one
of the most recognisable symbols of the Red Army, especially during World War
II. It was practical, easy to store, and usually made from khaki cotton or
wool. Similar versions of the side cap were later adopted by other armies,
including Italian and German forces during the World Wars. Variations of the
garrison cap are still worn today, particularly in the U.S. Air Force.
Even though it was never meant to be a fashion item, the pilotka has occasionally been picked up in style circles because of what it represents. Military headwear often carries ideas of discipline, rebellion, or heritage. The beret has definitely had more time in the spotlight—thanks to figures like Che Guevara and the Black Panthers—but the pilotka sits in a similar space, just in a much quieter way. These days, it’s mostly worn by collectors, re-enactors, or history enthusiasts, and it rarely shows up in mainstream fashion. Unlike the beret, which keeps coming back on runways at houses like Dior or Louis Vuitton, the pilotka tends to feel more at home in styled or vintage-inspired looks than everyday outfits.
That said, the garrison cap can work really well
when it’s styled thoughtfully. In this outfit, I’ve paired it with a teal-blue
V-neck sweater with dark red and white detailing, layered over a crisp white
button-up shirt. Pleated ivory trousers keep everything balanced, finished with
a red leather belt and gold buckle. The multicolour striped socks add a bit of
fun, while grey lace-up shoes keep things simple and grounded. The vintage blue
trench coat pulls the whole look together, echoing the colour palette and
leaning into that military feel. It’s a classic long-length style with all the
right details—epaulettes, a storm shield, sleeve loops, and a back vent. To
give the silhouette a bit more shape, I’ve added a chunky leather belt in a
matching blue tone at the waist. Gloves are a winter essential for me, and the
two-tone pair I’m wearing subtly picks up on the coat’s buttons.
Brown-and-ivory colour-block sunglasses add a modern touch, and finally, the
vintage laptop pouch finishes the look. It’s a colourful fabric piece showing a
Victorian-era horse race, trimmed with brown leather sides—small detail, but
one that adds personality, history, and a bit of storytelling to the outfit.
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