Creative Cover 002 – Kenny Annan-Jonathan : DESIGNER, MENTOR, FAMILY MAN


They say the average lifespan of every start-up business is three years, after three years if you survive the struggles of an entrepreneur, it’ll push your limits and teach you things about yourself you didn’t know. Kenny has experienced a decade of dressing how he feels and influenced many to do the same with through his brand, Playdot Apparel.

We met up with Kenny on a day like any other day, schedule packed and on the move as always. We got to watch him being documented and were part of the documentary as the shots were taken for this cover. It has been a while since we linked up with Kenny, and there was a lot to catch up on as he is a friend as well as the second creative cover star.

December officially marks 10 years of Playdot Apparel’s lifespan so we had to sit with him and talk about the year’s journey, the trials and tribulations as well as the success of growing a brand globally.

We start our journey in Croydon South London where Kenny lives before heading off to the ‘dress how you feel HQ’. As we get ready, cameras are all on us and we notice Kenny’s wife looking at flights to LA for this year’s Complexcon for the team, we’re told this is a spontaneous creative decision.

As we are looking at his different outfits, we see both old and new collections and discuss our favourites. Kenny adds; “the new stuff is something special” going through designs on his laptop and as well as his stock. “It’s going to be a great way to celebrate the longevity we’ve had in fashion”.

He says in an excited tone, as he puts on his Comme De Garcons x Converse trainers alongside a new Playdot release that complements the outfit while posing away with years of Playdot Apparel collections behind him.

You can tell that Kenny has studied fashion thoroughly. From what he wears, to his personal favourite brands, and how he talks about pushing the boundaries within his field. Shoot done, we decide to relax and talk more on the ten-year stretch and what it means to have reached this point while being a Designer, Mentor, and Family Man.  


So 10 years has passed did you think you would make it this far?

‘No way, I was just making clothes for now, at the beginning I hadn’t really had any commitment in anything so I wasn’t thinking of it as something where I need to set goals that would last that long. It was almost like a hobby now we’re here.’

So at what point did you think this is something big?

‘Even though the brand started in 2007, we didn’t have our Skitz character till 2009. When we saw the reaction towards the Skitz character that’s when I knew that this could blow.’


Thinking retrospectively, what particular milestones do you think that any brand should have hit within 10 years?

‘I actually really hate putting pressure on people, everyone moves at different paces, we should not beat ourselves up about meeting certain goals. Of course I had goals for the brand that I wanted to meet in terms of growth but there is nothing solid. For me it’s just about pushing through. I was still young, I just wanted to get to my end results.’


What were some of the turning points of the brand in the last 10 years?

‘When we released our stadium jackets that was big because it was one of our first pieces of Cut and Sew Garments. We also did a pop-up with Robot Bunny, and we released the stadium jackets on that day, and randomly Dappy from N-Dubz was wearing it at V-Festival on the same day! So people were watching it and then after they had finished watching the festival, they were coming into the pop-up store to buy the jacket!

When Odell Beckham was wearing our Hockey Jersey, this Jersey has really done a lot for us as we have sold it to a diverse market. We put in a pre-order for the jersey and when we did that, we sold out. Even in our restock, 82% of our customers were from the U.S!

Finally our most recent game changer came with the release of our camo truckers. I’ve always wanted to experiment with hats but we never had the right manufacturer, but instantly we had an amazing response to them! We have really pushed the boundaries by selling to people who wouldn’t normally wear street wear especially with these colours.’

What has been the most challenging parts of the last 10 years?

‘The transition of going from a local brand selling to friends to working on e-commerce has been tough! Another one would be always creating but not having the finances or materials to bring them to fruition. Also the balance between being a husband, a father, and a brand owner, is tough because I never want to neglect my family for the sake of my business.’


Next 10 years?

‘Whilst we are a fashion brand, I do gravitate towards a whole lifestyle aspect, meaning that it’s not just about the clothes, it’s also about art, collectibles, furnishing, having a part in people’s everyday lives. Only now have we released the Vinyl toy which is something I am heavily into and I want others to be the same. Just like people are into Takashi Murakami and Kaws, I want to venture out into bigger things outside of the fashion remit.’ 

Are you looking to have a more international presence?

‘When we launched with Lids – which is world’s biggest hat distribution company we viewed this as our stateside introduction and because the response was so amazing they would like to have a second collaboration in the future.’ 


You’ve been around for 10 years you’ve seen brands come and go, there are some brands you see and you will want to help them because you believe in it, which brands are these and why do you want to mentor their designers?

‘Certainly for me it’s about the people behind the brand. For example NNC London that’s a brand that I love to support, I know that they put a lot of work into it and I know that their reason for being in this industry is genuine. In some cases they have pushed boundaries far quicker than I did when I started out. Their hard work is inspiring and I will always support in whatever way I can.’

Which piece of advice sticks out most to you that you always pass on?

‘Always remember to love what you do. Finances are a by-product of the love that you have for your brand. Another piece of advice that was actually given to me was that if you are working with a business partner, make sure that you guys are right. If you guys are right then that is what matters. Understand how each other work, do not take offence to decisions and ideas. As long as you and your partner are aligned and have a good relationship that is what matters. I know people say don’t mix friendship and business but I feel it can work if it’s treated right.’

Are there any people in the fashion or arts world that you would like to be mentored by?

Nigo – Founder of Bape, now creative director of Uni-Qlo. Absolutely Iconic and definitely one of my influences

Pharrell- His creativity is always pushing the envelope. Even putting a song into a time lock that is crazy to me.

Brian Donnelly – Creator of Kaws- because his approach to life in general is a humble one.

Do you think there’s ever a time where you can advise a designer to quit the day job when the creativity has gone?

‘No, it’s never up to another man to dictate when someone is over. A designer can do anything they put their mind to. You can’t sell people your passion. Even when I put out Skitz, a lot of people did not know what else I can do with the face, how many other emotions it could show. I’m not in a position to tell a brand when to end, it will last as long as you want it to.’

Who are you mentors in real life?

‘My Pastor – my pastor is my life coach on a spiritual level. I have been feeling like I’m hitting a wall in terms of branding myself as an individual and I have not had a mentor to help me understand how to overcome that and maybe I will.’ 



How did your life change when you got married and became a dad?

To be honest at first I didn’t think it changed anything, but then later I realized, I went from a young man chasing a dream to man chasing a dream to support a family, divide my time and share my world. It made me take life more seriously because my decisions don’t just affect me.

What role do you think your family have had in you having a successful brand?

‘My wife has allowed me to have the headspace I need to create in my own time, network, and push the brand in whatever way. Even when this has meant we have had less time to do things. She also gives me her honest opinion, I know she has a good eye for it so she has the final say on ideas I have come up with. I enjoy speaking to her about the direction I have in my head for the brand. Even my daughter has had influence. The colors on some of the pieces are due to the emotions that I feel, these emotions are inspired by my daughter. She gives me a fun and positive aspect on the brand. Watching her being creative, even if she is just playing with lego, keeps my creativity alive.’

Do you think a 50/50 balance can be achieved between fashion and family?

‘I can’t say 50/50 because under no circumstances can the brand come before my family. I love Playdot to death but if push came to shove my family comes above all without a doubt. It is evenly balanced based on what I need to do but I wouldn’t say that balance is 50/50. I have learnt now to prioritize better and know what to sacrifice in order to spend more time with my family.’

Will we ever see a more obvious representation of your family in your brand?

‘Definitely in the future, this is the natural progression of life to want to show those that inspire you the most. It might be done in an obscure way but it will be there. There will be a story behind what we put out and most certainly some will link to my family.’

Speaking a little more near-term what can we expect for 2018?

‘So, we have a pop up store in an Art Gallery in the Philippines, this is a renowned gallery. We also have a collaboration with the individual that runs the gallery but can’t say who. Just know that this is good for the culture. We will be doing a pop up store for Part 2 of our collaboration with Long Live. We have others as well but it is too early to disclose – all we can say is watch this space. This is going to be THE YEAR OF THE COLLAB!’


You can purchase the official cover in our store and you can also get the exclusive 10 year Playdot collectors Cover











Words by Jojo Vandalkidd

Photography by FromNicksLens

Cover Design by Jamain Gordon

Styling by Kenny Annan-Jonathan (Playdot Apparel, Comme De Garcons, Converse)

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