Jay Pond-Jones has navigated a remarkable and multifaceted career. He began his professional journey training as a Graphic Designer, which led to roles as an Art Director and eventually a celebrated Creative Director in the advertising industry. Throughout his career, Jay has collaborated with leading brands, where his expertise and creative vision have left a lasting cultural impact. However, his journey didn’t stop there. Jay ventured into the comedy scene, where he made a significant mark by creating, producing, and directing TV shows, as well as creating live stand-up comedy events across London under the @colourfulcontentcomedy banner.
Beyond his work in comedy and advertising, Jay’s entrepreneurial spirit has led him to launch several successful ventures. He founded ColourBolt, a distinctive bike brand recognized for its unique design and craftsmanship. More recently, he introduced Jay Boy, Jay’s very own clothing line, starting with a line of Bucket hats that reflects his deep passion for design and the Ivy League look we all know and love. With plans for expansion, this latest endeavour adds another exciting chapter to Jay’s dynamic and ever-evolving career. We sat down with Jay to learn more about his life, career, the importance of a well-fitting pair of Sta-Prest and why Levi’s iconic 1954 501z, might be the most versatile denim cut known to man.
CAN YOU REMEMBER THE FIRST SIGNIFICANT PIECE OF CLOTHING YOU PURCHASED? WHAT WAS IT AND WHERE WAS IT BOUGHT?
I’d have to say it was a pair of black Levi’s Sta-Prest trousers. I bought them when I was 13 from Michael Martins in Uxbridge. The store had Sta-Prest in every colour, tonic suits, Prince of Wales check trousers, and Ben Sherman shirts – pretty much everything you could want!
At the time, it was all about finding ways to navigate the strict school uniform rules. The black Sta-Prest trousers were acceptable, and I managed to get away with wearing a black barathea blazer instead of the standard blue one. I also had a pair of ‘aubergine’ loafers instead of black, and a beige Brutus button-down shirt that I bought at Hayes Market. It was definitely an upgrade from the standard school uniform.
This is probably why many years later I was so happy to find Real Hoxton’s Stay Pressed – which are even better than the originals in my view.
WHEN WAS YOUR FIRST VISIT TO THE SHOP AND WHAT WERE YOUR FIRST IMPRESSIONS?
I remember window shopping at The Squire Shop on Brewer Street – probably because I was only earning £7 a week as a messenger in a commercial art studio on Goodge Street. So, gazing through the windows was as far as I got. My first proper John Simons experience was at Russell Street. The feeling I had then, and still have today, is that I would happily wear everything in the shop. It was like discovering all the clothes and shoes I had ever wanted, all in one place. It was, and still is, the best.
WHAT ITEM OF CLOTHING COULD YOU NOT LIVE WITHOUT?
I’ve collected so many clothes over the years that anything I buy now is something I’ve convinced myself I can’t live without. My most recent must-have purchase was a pair of black suede Playboy shoes. It’s definitely worth having a read about them on the John Simons site. Going to my out-of-town lock-up is like shopping in my own store, which is pretty much what I do when I go there to swap a few things out.
I’d certainly include Levi’s 501z in the “couldn’t-live-without” list. I love the slightly slimmer silhouette of this zip-fly version. They were first introduced on the East Coast of America in 1954, where they were the preferred alternative to the button fly. You can pair them with anything. They look great with an M-65 jacket or a classic sports coat. I have them in all variations, from unwashed, to every degree of fade, with different length options, and with or without the all-important half-inch turn-up.
I know it sounds obsessive, but if the length is off by just the smallest amount for the shoes or boots, I’m wearing, it doesn’t feel right. I’m under no delusions that this is normal behaviour! When I wear Redwing boots, I usually go for the 1966 Levi’s 501 because the slightly wider leg opening sits perfectly. To me, these details are important. I suppose it’s my original background as a graphic designer – things need to be precise.
WHAT IS YOUR NUMBER ONE STYLE TIP FOR THE READERS AT HOME?
Find your thing, and then work around that. I don’t want to spend too much time thinking about what to wear every day. Plus, get a small portable steamer.
DO YOU HAVE A SARTORIAL HERO?
Charlie Watts. There’s an amazing book of Rolling Stones photographs on the table next to the lift at White City House. Whenever I’m waiting there, I always find a good picture of Charlie and leave it open on that spread.
IF YOU COULD CHOOSE TO ATTEND A CONCERT FROM ANY ARTIST, DEAD OR ALIVE, WHO WOULD IT BE AND WHAT WOULD YOU WEAR?
James Brown’s ‘Live at The Apollo’ show in October 1962 would have to be my choice. The live recording captured his raw energy and brought it to a broader audience. It played a huge role in celebrating Black cultural excellence and elevating African American artists. Additionally, it supported the civil rights movement by showcasing the incredible talent of Black performers. This album’s success set the stage for James Brown’s lasting influence on funk, soul, and eventually hip-hop, cementing his legacy as a pioneer.
I’d wear an Ivy suit, probably in dark grey cotton from Brooks Brothers, paired with a navy button-down shirt, white socks, and highly polished black loafers. I’d complete the look with a black silk knitted tie, which I’d allow myself to loosen very slightly as the temperature rose in The Apollo over the course of the evening.
YOU CLEARLY LIKE YOUR CLOTHES. WHAT TOOK YOU SO LONG TO START JAY BOY?
I actually branded my first Jay Boy item back in 1974 when I was just 17. I had just started working as a trainee commercial artist, and everyone called me Jay Boy. I remember using white Letraset to rub down the word “JAYBOY” on the side of a pair of loafers. Unfortunately, the letrafix spray I used didn’t do the job, and the letters peeled off the first time I wore them. I even used the Futura font!
Fast forward 50 years, and I decided to give it another go, this time starting with my ‘Snap-Brim Bucket Hat’. The whole JAY BOY brand look is a nod to my formative years, including the use of Letratone rubdowns in the illustrations. With a 50-year pause, I’ve had plenty of time to think it through!
