An Afternoon With Winston’s Legacy

TVG dropped by Winston’s Legacy HQ for a coffee and a chat with co-owner Dave Liddell about handcrafted neckwear, Winston Churchill and doing what you love. 

Firstly, for those that haven’t heard of your brand, who and what is Winston’s Legacy?
Winston’s Legacy is a menswear label that started mid-last year. We are made up of two brothers with a passion for the finer things in life, and we love the idea that something as simple as a bow-tie or pocket-square can really ignite someone’s outfit and the way they carry themselves.



Your name and logo obviously takes inspiration from Winston Churchill, what was the thought process behind this?
Winston Churchill described wearing a bow-tie as a ‘statement maker’. We have always been big fans of Churchill, not so much from a political point of view, more as a style icon. He wore trenches, sported bow ties and blazed big old cigars. The controversy that surrounded him has kept him in the spotlight for decades and we wanted to (potentially) carry on his legacy in some small way.


Tell us a bit about the business, who, when, where, why?
We first had the idea a way back in 2008 when we lived together in London and fell in love with the attention to detail in the English gentleman’s wardrobe. Around mid-last year we decided it was time to take the gamble. I quit my job, we bought a sewing machine and since have spent countless hours teaching ourselves the craftsmanship of sewing.


My brother and I started the business because we have always had a keen interest in men’s style and a drive to create something special. We want to make a difference. We want our clientele to feel confident wearing our pieces because the can really set you apart from the mundane world of Australian menswear. We have big dreams however we understand it will take time.



Where do you source your fabrics and who makes your products?
We source our fabric from local stores as well as spending countless hours browsing the web finding the right yardage we are after. Our fabric all comes from Japan and Italy and we produce everything here in Sydney.



Where can we buy your products and how has the response been so far?
Coming from a digital background, we have decided to focus on an online store for now that is minimalistic and user friendly. We offer complimentary worldwide shipping and have received a great response from international customers – gaining orders from France, Italy, the UK and especially the States. We currently have our products in half a dozen Sydney stores & one in Melbourne. The response has been fantastic and exactly as envisioned. Our stockists have been incredibly supportive and more often than not we find ourselves ‘sold-out’ and it’s back to the ‘sweat-shop’ for more sewing!


Your packaging is excellent, how important is the entire ‘package’ for a product like yours?
After years of observing the market, we decided that packaging was just as important as the product itself. It sounds cliché, but we want a purchase from Winston’s to be an experience rather than a one off. We are constantly improving our packaging and thinking of new ideas to set us apart from the competition. The aim is for our client to have a great initial experience, hopefully reuse their packaging to store cufflinks or collarbones and most importantly, tell their friends.



What’s been your greatest challenge and achievement so far?
Learning to sew was a real struggle – after plenty of coffee, whisky & late nights, we were able to produce the hand-crafted product we had envisaged. Finances have also been a challenge because as much as creativity goes into it, at the end of the day, it is all about cents and dollars. After quitting my job I’ve been eating into the savings and making full use of credit cards – thanks NAB. If it was easy though, everyone would be doing it, and we have come to terms with the fact that it will take a long, long time until we can sit back and have a full night sleep, until then, head down and bum up!


What’s next for Winston’s? You previously did a stint at Polo shirts, will we see shirts in the future?
Most definitely, however for now we want to focus on accessories and really own the space we are in. Down the track we will potentially start thinking about next steps, whether it be knitwear, leather goods or shirting – for now we are happy to focus on neckwear and pocket squares.


Finally, what advice would you give to someone out there looking to start their own business?
Be prepared to spend the first few years poor, very, very poor. It takes ten years to become an overnight success…



James is the Founder and Editor of The Versatile Gent.

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