A fitted cap veteran, Alessandro’s obsession with headwear spans 20 years, making his first 59FIFTY fitted purchase before he even entered high school. It was the classic Yankees cap that first caught his eye, although his keenness was undone by the error of getting the wrong size, a mistake he would not repeat.

Now with a staggering cap collection which exceeds well over 100 pieces, Alessandro has a penchant for MLB Fitteds. His cap choice is a reflection of his style, both vibrant and innovative, he uses his selection to coordinate his 59FIFTY with his sneakers to good effect. 

Alessandro cites the dirty south rappers of the early 2000’s as the inspiration behind his love for fitted caps. A staple during this era of music, it was these rappers who influenced his style and gave birth to his contemporary mix of both US and European mix of fashion trends. When it comes to getting ready for the day he’s a fitted first person, opting to let his headwear dictate the rest of his outfit.

His undoubted go-to cap of choice is the Cincinnati Reds On-Field, “no patch, grey brim”. A cap that resonates so strongly with Alessandro that he has lost count of the number of times he has purchased this particular 59FIFTY.

Having seen the rise and rebirth of fitted cap culture, Alessandro notes the evolution of the 59FIFTY, where once you could easily purchase a cap of your choice, he now finds that the growth in popularity sometimes even forces him to purchase caps at resell – a sign of broadening appreciation for fitteds both as a sportwear item and fashion accessory. His current most coveted cap is his red Paper Planes 59FIFTY, a hat which doesn’t see many regular releases. Alongside this his favourite cap is the all-black Seattle Mariners, another rare release.

To him this is more than just his collection of caps, these are symbols of the taste and culture which over the years has grown to define and embody his personal aesthetic, which bleeds into not only his style but also his artistry and influence as a creator. Even after over 20 years Alessandro’s passion for headwear remains intact, still feeling the buzz of seeing a new fitted colourway he has to have, as strong as ever.

Checkout Alessandro’s collection below and show him some love @sgamo1990.