The End of an Era


When we started Gilmour & Gray in 2013 Charlie and I knew that it would be a huge undertaking and we didn’t take this lightly. Backed by our family and with momentous support from our parents, we were full of enthusiasm and ready to crack on.

It was the best idea and still is we think. Charlie and I were young wannabe entrepreneurs keen to make our mark with a new fresh idea. We made our mark in our own way, but it has not worked out as we had planned. Hopefully there will be some insight in this blog to help future entrepreneurs. Also, we would like to use this as an opportunity to share our gratitude to our family, friends and customers who came on the journey with us, and explain why it hasn’t worked out.

The idea - Chelsea boots with a one-piece leather design (akin to a certain Australian brand) with coloured elastic - everyone we spoke to loved it – this was our market testing! At the time we had not seen this design anywhere else. It turns out we were close to cutting edge however became aware that Penelope Chilvers had already designed something similar. This did not dampen our enthusiasm but instead fuelled our view that this was a good idea and one to be pursued. Our boots were also going to be targeting a different market so we felt we had a place in the market, with a unique brand and strong story.

The beginning..

In 2012 around the London Olympics, Charlie mentioned whilst having a pint and listening to a band in the Shacklewell Arms that he wanted to start a business and knew of a government scheme that would help financially towards a venture. David Cameron brought together a group of businessmen, women and dragons, who would mentor young entrepreneurs with new business ideas. It was called Brightside. Charlie and I went along to one of the meetings to find out what it was all about and were encouraged by what we heard and saw. We needed to build a business plan and pitch for the funding in a ‘Dragon’s Den’ like set up. We were off.

At the time..

At the time Charlie was waiting tables at events, fully qualified as a sound engineer from Point Black Studios and had an EP release behind him. The nature of the royalties ensured he still needed to work full time elsewhere. I, Nick, had been working in the city in insurance as a trainee broker and was not overly fulfilled or very good at it. I had been between a few jobs and was looking for something different that would enable me to be creative and the thought of working with my brother on an innovative and forward-thinking business, felt exciting. This formed the basis for our intrigue in Brightside and the business grants on offer. It was Charlie though that was astute enough to bring the Brightside scheme to the table.

As the oldest two of four we are different in many ways, had spent a few years living different lives whilst still living in the same London. This was a great way of us re-connecting as brothers and bringing our different styles together to the G&G brand.

Next steps..

Once we had decided we wanted to start a business, we quickly came to our idea. As our website says we grew up in a family where R.M Williams were the boot to wear for adults and cool kids who tried to look like cowboys.

‘Forget the cool kids and our parents’ friends’ Charlie would tell me, ‘they are wearing these boots in the Shacklewell Arms son - 😉’.

Chelsea boots that sell to our parents’ generation and the younger kids, wherever they were. East London meets West was our thinking. Town meets country.

Chelsea boots, unrelated to us, went on to be the boot worn by everyone from Pete Doherty to Beckham and more importantly the high street. Not because of us, obviously, but because a timeless classic was reborn. We started the business during this time. I repeat nothing to do with us, but it validated our idea which was great.

We then set about researching the idea and meeting suppliers. We went to Bethnal Green High Road to meet a supplier who worked with Gucci making elastic, he was helpful and liked two young brothers who showed some passion for fashion. I started meeting design guys and Charlie started sourcing manufacturers with trips to Portugal – port and cheese helped!

We then went to the BrightSide events, pitched our idea and one of the mentors was wearing RM Williams boots. He loved the idea and again it was a validation of what we trying to do.

We put the numbers together for sales projections and modelled our P&L, target margin and revenue and were awarded £19,000 of funding. This was not a grant it was a business loan to two budding entrepreneurs who otherwise would never have got a business loan from a bank. It was a great thing.

With the funding we set about sampling the boots from manufacturers all over Europe. We were specific about the requirement of manufacturing one-piece leather boots like RM Williams and this in the end was a real issue for the factories, but we persisted. This one-piece leather design was a big part of our pitch, and a key element to making us stand out, so we had to get this right.

The Launch..

We found a manufacturer in Portugal who made a few samples as we wanted and subsequently, we ordered a few hundred pairs across various sizes - using only a finger in the air as a guide for which sizes to major on.

My wife Tilly was working in Knightsbridge at the time and there was a pop-up shop next door which we used for the launch of our boots. It was the most amazing evening and Charlie and I felt like we had made it before we had even started! Everyone was trying on boots and buying a plenty. Mostly friends and family but still, they liked the product and were complimentary.

We had a great brand and already a good following of people online, through friends and family and this continued for some time. The lesson I take is that all this ‘good will’ didn’t mean anything in terms of cash in the bank and ROI. We had fun though and it was good to announce our launch and first trading.


Inevitably Chelsea boots brings comparisons to polo. Polo players wear them, and we had contacts in the industry, so it was a good place to market our boots.

We partnered with British Polo Day and sponsored an event in Beijing. Our boots were made in China by now and the bosses of the factory went to the British Polo Day in China and were impressed with the prestigious set up Gilmour & Gray had introduced them too. We also passed our boots on to the Princes at this time through polo prizes and so the brand was doing well but the sales were not providing enough margin to support the business.

Our manufacturers were asking for more and more volumes to be ordered and due to the lack of margin in our sales price we were not able to re-order in the quantities the factory needed. This resulted in us us not being able to re-stock some sizes, which understandably did not look so good on our site.


Continuing to pursue the polo line we attended the Guards Polo event in Petworth. We had a large stand opposite Jack Wills and did a roaring trade. After the event we were down £2,000, despite selling over 50 pairs and the writing was on the wall. We were not selling enough; the margin wasn’t good enough and the business was not making enough money.

We ran before we could walk with this event and pitched our tent opposite some much larger brands. We partnered with a Gin brand, were handing out drinks and selling lots of boots but again the event ended up costing us money. The idea that the brand would ultimately develop, and grow was proving difficult as we needed funding to support these sort of events. We could not rely on the profit from sales to attend these events in this way.


Trying to predict the volumes to order and which would be the most popular was challenging. Our first batch sold very well and more of the smaller sizes. Our second batch we sold more of the larger sizes and so on until we had a garage full of boots…hence the sale now 😉. One consistent was Mens 9’s and 10’s. Women’s was a full range from 3-9.

I was so excited about our black and pink boots, convinced they would be bought by men for parties and girls alike. My wife Tillz shared a picture of one of the samples on Instagram and subsequently we received a considerable amount of interest, however another learning curve was that we couldn’t meet the demands of the quick turn-around expected by the online consumer.

Another learning curve was our marketing efforts - we didn’t dive deep enough into this. We did have a lovely quarter page feature in The Telegraph Magazine which resulted in 20 orders that day – which in hindsight showcases how investment in PR and marketing could have had a beneficial impact on our sales. Ultimately, because we both had second jobs our focus was divided, the signs were there that we were struggling to take the company from the successful SME in its infancy to a medium business growing and ready for SEED round investment.

The supply chain continued to be the most difficult part of G&G. From perfect samples then quality control issues, to minimum order quantities that were difficult to justify for a small start-up, it was a difficult nut to crack. Our advice to all those starting a fashion business would be to ensure your supply chain is aware of your plans for growth, to manage expectations around order quantities and ensure your supplier is onboard with the quality standard you set.


When we started the business, we studied the market and carried out our research into competitors, price point and direct and in-direct methods of sale. We had an issue with wholesalers as they tended to want to retail at 2.5 times the purchase price. We bought at a price and retailed on our website – more reasonable than a wholesaler would retail and this meant we could not sell our boots to wholesalers. Confusing?

This was a route to market we could not capitalise on, hindered our sales volumes and the prospects of the business’ success were therefore affected.

The lesson here is to make sure you cater for the wholesale market within your retail price point. It is too big a route to market to miss.

We thought we could rely on online sales, but it is difficult to reach certain markets without wholesalers.

Life takes over..

The Gilmour & Gray journey was born out of a determination to do something different and build a business for the future, for both of us. However over the five years we reached a point where we both had to decide if we were going to go full time on Gilmour & Gray or continue our ‘day jobs’. When your career is providing you with more security you have a decision to make.

G&G was our passion but it had become something that was second fiddle to my career and with a young family to support a decision had to be made. Some more brave or daring individuals would have continued with the G&G project but when we weighed up our options we decided to concentrate on other areas. Not an easy decision to make as we loved our work on G&G and the photos in this blog are testament to the fun we had and small success we enjoyed.

Christmas closing down sale..

So! We now have our Christmas Closing Down Sale. It’s a sad sight to see the Closing Down Sale banner across the page but also an opportunity to look back and reflect on so many good times.


We thank all of our friends - you know who you are! - who have helped out with G&G and provided huge support over the years.

You were also our customers which meant you were really an important part of this, so thanks again to our mates.

Maybe a final plug to get your hands on one last pair of G&G boots! ABC!

Gray Store

The most amazing thing about this journey is that post the G&G venture, we have a new project through which we can adopt all the learnings from this project.

Gray Store is Charlie’s brainchild and will manufacture trainers from only ethically sourced materials; manmade leather replacement fabric from specialists in Portugal and Italy. Yes, the supply chain has been thought through very carefully!

There are many lessons, some highlighted above that will stand this venture in good stead and I hope you will all support this venture as you have G&G. We will keep your email addresses on file for Gray Store if that’s ok but please let us know if you would like to un-subscribe.

Final thought..

Do as we did, be adventurous, follow your dream and set up the venture you believe will succeed but don’t do this part time. It must be your sole focus.

Thanks to our customers..

We really appreciate all your support over the last five years. We have had the best time providing you all with Chelsea boots that we hope you have enjoyed wearing. We promise you aways looked the part 😉

If you have any questions for either of us please contact –