Award-winning designer Keegan Simon wears creativity on his sleeve

Discipline, tolerance and production. These are well known as the national watchwords of Trinidad and Tobago, but one man has a different take.

Perhaps best known for his own Watchwords merchandise, which features words synonymous with local culture, Keegan Simon is a T-shirt designer and self-described "creative" who primarily grew up in Belmont, Port of Spain.

His mother was a flight attendant, allowing him to take frequent trips to Toronto and London, among other places, and spend lengths of time there.

Simon believes these frequent trips and the influence of his cousin Jameel Sagar helped mould him.

“As young as six, I had a cousin that I idolised and I wanted to be like him. He was very creative, so I was like, ‘This is something I have to do.’

“As long as I remember, I wanted to do something like him. When I was eight or nine, I realised what creativity is, and it was like, ‘You want to create something, you want to do something.’”

His education provided the framework to build on that creativity. His school, St James Government Secondary, offered over 20 different subjects.

“You could have done woodwork, metalwork, HSB (human and social biology), 'home ec' (home economics). You could have done any of those things, and it was valuable, so I really really loved what St James had to offer.”

He went on to Edna Manley College in Kingston, Jamaica, where he graduated with a bachelor of fine arts in painting before working toward his masters in creative design and entrepreneurship at UWI, St Augustine.

“Edna (Manley College) was one of the best experiences, because you had all these creatives finding different outlets to do things.

“I remember someone who, at midnight, would scream at the top of their lungs, I’m assuming as part of their acting. It was very cool to see different ways of creativity just be a part of one place.”

While at the college, he met Marlon James, a Jamaican photographer now based in Trinidad, who was then the lab tech and teaching assistant in the photography department. The pair became fast friends.

In a phone call with Newsday, James said, “I remember he would make T-shirt designs in the printing department or up in his room."

The pair worked together on projects like Simon’s venture Dirty Crayons – two exhibitions which featured art by Simon and Jamaican students Kemar Swaby, Leasho Johnson, Taj Francis and Jehan Jackson.

James added, “It was just an interesting body of work...different drawing styles and techniques combined in a exhibition.

“We’re good friends. When Keegan had ideas he’d run them by me. He used to call me the master of the in-between, because every time I would do a photoshoot, in the minute when the person wasn’t aware of the camera, I would capture it, and that would become the shot.”

“He is very much for the carefree and letting loose. His brand is all about the happiness. He’s found that way of tapping into mistakes, like when life gives you lemons and you make lemonade.

“I learnt a lot from him and a ton of great portraits came from working with him.”

Reminiscing about the college and its students, Simon said it was at the forefront of creativity in the Caribbean.

“It was so cool to see that the people that we are now were moulded by Edna, but we now are doing cool things around the world. I have friends who did work for Black Panther (the movie)...I had a friend who did the cover of Photoshop (a graphic design tool). I feel fortunate to be a part of that.”

That experience and education are still a part of his daily life.

“I use my creative knowledge a lot. (The programme) is just how I am now, because you get to mould creativity into a business structure.”

After graduating, Simon won the Royal Overseas League Art Showcase Residency in Scotland and the Annual Scholars Exhibition in London and an internship with Trinidad and Tobago advertising agency AboveGroup. He was one of four artists invited to assist in the Trinidad launch of vodka manufacturer Absolut's limited-edition Andy Warhol-inspired bottle design.

In 2012, he had the chance to work with soca legend Machel Montano as his creative director. He was responsible for visual concepts, merchandise designs and the stage design for Montano’s performances. He remained in this position for two years.

From 2016-18, Simon worked with The Lost Tribe as a costume designer, after creative director Valmiki Maharaj approached him. Initially, Simon created sketches around the idea of a dandelion, but after input from Maharaj, the idea was transformed.

“At the end of it he was like, ‘Scrap this. Let’s take the 'dandi' out of this, make this a lion and turn this into a piece.’

“And that’s what became the first costume I did, which was Roar of the Road, which is a lion.

"And the whole process was so cool, working with (members of the Lost Tribe team) Val (Valmiki Maharaj), Anya (Ayoung Chee), Chris (Boodoo), Matthew (Blackman) and JP (Richardson).”

“I think it was one of the first sections to sell out, it was so unique.”

The public reaction to his first Lost Tribe design exceeded Simon’s expectations. He recalled first seeing the costume on the road bringing him to tears.

His second year was a challenging one, as Simon was set on repeating his success.

“Don’t be a one-trick pony. What if someone took away all of your tricks? How do you start over?’ I started thinking of innovation."

So he brought silent headphones to the band. With music trucks not allowed to play along certain areas of the parade route, specifically near the Port of Spain General Hospital, an area prone to congestion, bands are often stuck in silence. Simon's silent headphones connected directly to the DJ’s equipment, allowing masqueraders to continue their enjoyment while still maintaining the peace.

After three years with the band, Simon decided to focus on his own brand, 1ndividual Aesthetic (pronounced individual). Inspired by skateboard culture and design, Simon took those elements and injected his own personal style. Although created in 2015, 1ndividual wasn’t Simon’s top priority, as his focus was divided between his education and other projects.

He thought his life would be one where he passed on his knowledge and ideas.

"But I went in a different direction. I got back to 1ndividual I would probably say in December 2018 or the start of 2019.”

Initially, when refocusing on his brand, he recalled feeling unmotivated.

“I didn’t know what I was doing. I didn’t feel to do 1ndividual.”

So he turned to his friends.

“It’s a funny story, actually. I never thought I would be a market guy. A very good friend of mine actually said, ‘Why not try the markets?’”

So Simon took part in his first UpMarket, the (usually monthly) food and craft market for small businesses and artisans, and was shocked at its profitability when he made $5,000.

“I said to myself, ‘This is what it is?’ and my whole brain changed. Especially in the landscape that we live in in Trinidad and Tobago, markets are one of the best business-to-consumer interactions you could ever have.”

He now believes every business should take part in a market because it allows owners to use the feedback they get from customers to improve their processes.

“I would say from then to now, markets have really helped me love 1ndividual again.”

Simon uses the brand as a way to showcase his perspectives.

“It’s only recently I’ve understood that it’s my version of things. It’s not a matter of beauty, it’s my version of what Trinidad and Tobago is. It could be the Watchwords (referring to the shirt he was wearing) or the Thanos, which is my version of what soca is.”

To Simon, collaboration has been a key component in his growth so far as it allowed him to learn and grow. Likening his collaborations to the symbiotic relationship between comic-book character Venom and its host, Eddie Brock, he said, “That was one of my first steps when I came back to Trinidad.

“Just like Venom, I said to myself, ‘If I want to do these things, I have to latch onto a larger person to get these things done.’ So that’s when I started to do collaborations.”

Those collaborations started with Scorch, the local magazine and radio station, where he designed T-shirts for Panorama semifinals, which led to Simon consulting on projects for four years. That in turn led to working with artists like Bunji Garlin and Kees Dieffenthaller.

“I knew how important and invaluable my creativity was for that. Those things helped to buy the equipment and to get the printery to where it is now.

“I was very blessed to see the fruits of it, because I could have never done that if it was just myself.”

To this point, 1ndividual has been a one-man show, with Simon creating all his designs and printing the merchandise. Being so hands-on has allowed him to plan every element, down to the finest details. Simon, a self-professed fan of puns and Easter eggs (hidden elements or meanings), adds them to every design. An example of this is in his Thanos merchandise: the design features two clasped arms with dozens of fete bands on each arm with the text: "Till Fete Do Us Part."

Many people can relate to this, as they collect their fete bands during the Carnival season, but the design goes even deeper. The prints feature a glow-in-the-dark overlay of the bone structure of the two arms, which only becomes visible under black light.

Although they were launched during the 2018 Carnival season, one customer recently tagged Simon on X (formerly Twitter) expressing his shock when he discovered this. Simon, explained, “The Easter egg is 'Till Fete Do Us Part.' I wanted to show even when we parted in the afterlife, we pumping still, with the skeleton.”

That level of attention to detail recently won Simon another gold ADDY from the Caribbean Advertising Federation, one of the most prestigious awards in the industry.

The gold ADDY was for the packaging of another of his designs, Living Single Eating Doubles. The bright yellow shirts were rolled, wrapped in greaseproof paper and put in a branded brown paper bag. This packaging also held hints at a future product release – the 1 Happy Place logo.

This was Simon’s second gold. The first was for his packaging inspired by spray-paint cans, which also received a special award called Best in Print.

Simon explained that even his awards had Easter eggs as well. For both entries, he listed members of his family who supported him through the process as team members, to honour their contributions. This meant that when he won his first gold, his mother did as well. His second was shared with his cousin.

Simon’s latest releases have been well-received. His One Happy Place hats feature a smiling face as the logo, with each eye replaced by drawings of Trinidad and Tobago. He initially planned a limited release, but the significant public interest has necessitated four additional releases so far.

“Now, my scalability has reached a point where as much as I love my printery, I realise that the printery was here for me to learn about quality control.

“Now I know that I am able to impart that knowledge to a larger scale, Trinidad is a lot more rewarding and a lot better for me to sink my teeth into.”

Simon plans to continue his growth by releasing the hats to both American and European markets and hopes to make the tagline, 2 Islands 1 Happy Place, the unofficial slogan of Trinidad and Tobago tourism.