Oliver Huddlestone is one of the most recognisable faces in the shirt game.
He's built one of the most engaged communities on social media around football shirt culture. Some of the biggest football clubs in the world have beaten down his door in the last year for a sprinkling of his stardust. He gets the modern fan's yearning for the good old days. He's one of them having not experienced the good old days himself in quite some time as a long-suffering Boro fan. More importantly, Olly is one of the nicest blokes you could meet. We sent our editor and fellow Boro lad, Lee Kelleher, to talk shirts.
Was there a shirt that sparked you becoming a collector or did it happen gradually?
I've always loved football shirts and fashion - trainers, jumpers, jackets, hats, the lot. I guess I started when I was about five or six, getting Boro and England shirts for my birthday and Christmas, but I obviously grew out of all my kits so had to buy them all again... and it has been a pricey process!
What was the first shirt you owned and do you still have it?
Boro home 1995-96. The first season at the Riverside. Juninho, Hignett, Barmby... what a time! I don't have the one I had back in the day, but I do have it in XXL with the Little Fella on the back.
Which shirt in your collection has the most sentimental value and why?
Possibly Boro's 2004 Carling Cup winning shirt with 'Juninho 10' on the back. The shirt itself is hideous, so uncomfortable to wear and the sizing is all over the gaff, but the memories of seeing my team lift the Carling Cup with my favourite player of all time on the pitch after a top day with my dad, you just can't beat that.
If your collection was a football team, which shirt would be the captain?
Italy 1994 with Maldini on the back. An iconic kit made famous for that Baggio penalty, but the man on the back just oozed class as a player and a captain. Greatest defender of all time.
Grails: Which shirt are you chasing?
Club America 1995. The Coca Cola sponsor, the colours, the iconic Adidas template, plus I'm missing a Club America shirt from my collection. I might have to get the latest for 2025/26 actually. Beauty!
One shirt you could save in a fire?
Probably my most valuable, an Inter 1992 player issue which is possibly matchworn. There's a real possibility it belonged to Dennis Bergkamp but I'm working to get that verified.
Right, let's get down to it. Give us your five favourite shirts in your collection, Olly.
I think I've got to start with Boro away from 1995. It's possibly my favourite shirt of all time, with my favourite player on the back: Juninho 25. The colours, the Cellnet sponsor, and the jacquard details - an unreal time to be a Boro fan. Banger!
Next up, England's home shirt from 1998. The first tournament I can remember watching and the heartbreak against Argentina - a proper World Cup classic. The shirt itself is a classic Umbro template and I'm a sucker for a centralised badge. Complete with England's 18-year-old wonderkid on the back.
Number three is England's third from 1992. It's criminal we never got to see this in a tournament. Umbro in the 90s was peak football - they just got it. I also wore this to the Euro 2024 semi-final in Dortmund. Ollie Watkins in the 89th minute! Without doubt the best game I've ever been to. Crazy memories.
Atletico's home shirt from 1997 is next up. The shirt that Juninho was presented in when he moved to Atletico Madrid after Boro's mental 1996/97 season that resulted in relegation from the Premier League. The first time I ever felt heartbreak as a football fan... but what a kit!
I've tried to avoid making all these about England and Boro. This PSG home shirt from 1994 is in there because I just love it. Nike were on top of their game that decade with the likes of Dortmund, PSV and PSG and this shirt just screams 90s. Vibrant colours, the central Nike logo and the biggest sponsor I've ever seen. Reminds me of Ginola. Classic!
We also think you'll like...