The Journey of Purpose
How a sketch on paper became a lifetime calling
I never chose fashion – fashion chose me.
From the moment I stepped into my first pattern-making class, I knew with absolute certainty that this was what I was meant to do. My soul demanded this path, not what I wanted to do or what seemed like a good career path. That clarity has carried me through every struggle, every setback, every moment of doubt over the past 17 years.
This is my story. Not the polished version you might expect, but the real one, filled with failures, pivots, losses, and the relentless pursuit of a vision that refused to let me go. It’s a story about finding your calling, no matter how unconventional the path.
The Beginning
Growing up, I knew deep inside that I was meant to do this, but at that age, I did not know what it would look like. In troublesome moments, I found peace in a different place, with a pencil in my hand and blank paper in front of me. I would draw for hours in my own quiet space, whenever I got the chance. Sometimes the images came from places I’d seen, sometimes from magazines or music videos, but most often, they were about beauty and fashion.
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I didn’t have formal training. I taught myself to sketch and shade, improvising different techniques. I just practised whenever I could because I loved the process, and it gave me so much peace. There was something meditative about bringing an idea to life on paper, about capturing a vision and making it tangible.
As I grew older, my interest evolved beyond just drawing. I became fascinated by style and its effect on culture. This was the era of hip-hop and R&B dominance, and the fashion was incredible. The way artists dressed wasn’t just about clothing; it was about identity, confidence, and character. When you dressed a certain way, you became someone. You felt different. More powerful. More yourself.
That’s when everything clicked for me. Art and fashion weren’t separate interests; they were two sides of the same creative vision. My brain started seeing things differently, making connections others didn’t see. Fashion wasn’t just about making clothes; it was about creating confidence, building identity, and telling stories through fabric and form.
The Rebellion
Despite this growing passion, I was never encouraged to follow this path; it was just my inner desire and love, which I kept to myself. I forced myself to believe that an alternative path was my best option; I found myself studying computer science and engineering. It wasn’t my choice; it was the “practical” path that was expected of me. Every day felt wrong. Where fashion and art filled me with energy, engineering drained me. The stress was overwhelming; the work was unfulfilling. I was living someone else’s vision for my life.
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Something had to break, and eventually, it did. I couldn’t continue on a path that was killing my spirit. So I rebelled. I broke from the mould and went soul searching, trying to figure out what my real purpose was. There were wrong turns and right turns, moments of clarity and periods of complete confusion.
Finally, after what felt like wandering in the dark, I made a decision that would change everything: I enrolled in a fashion design school here in Sydney.
"This was my calling, my soul's desire."
Harsh Realities
Graduating from fashion school filled me with optimism and ambition. I was ready to make my mark. But the Australian fashion industry had a very different welcome waiting for me. The reality was harsh: when you leave school, you don’t actually have much skill yet. Most of the real learning happens on the job, in real studios, working with experienced professionals. That’s where theory becomes practice. The problem? Almost every established designer or studio I approached was looking to exploit young designers as free labour. They’d dangle the promise of “experience” while using us to do actual production work without compensation.
It was a terrible, demoralising experience. I watched talented designers get used and discarded. I saw the system designed to benefit those already established while crushing those trying to break in. After multiple disappointing attempts to find legitimate opportunities, I made a decision: I’m not playing this game. If the industry won’t give me a fair chance to learn and grow, I’ll create my own path.
With whatever limited experience I’d managed to gain, I decided to go on my own. It was terrifying and probably premature, but staying in that exploitative system would have destroyed my passion before I ever got started.
Graduating from fashion school filled me with optimism and ambition. I was ready to make my mark. But the Australian fashion industry had a very different welcome waiting for me. The reality was harsh: when you leave school, you don’t actually have much skill yet. Most of the real learning happens on the job, in real studios, working with experienced professionals. That’s where theory becomes practice. The problem?
Read More
Almost every established designer or studio I approached was looking to exploit young designers as free labour. They’d dangle the promise of “experience” while using us to do actual production work without compensation.
It was a terrible, demoralising experience. I watched talented designers get used and discarded. I saw the system designed to benefit those already established while crushing those trying to break in. After multiple disappointing attempts to find legitimate opportunities, I made a decision: I’m not playing this game. If the industry won’t give me a fair chance to learn and grow, I’ll create my own path.
With whatever limited experience I’d managed to gain, I decided to go on my own. It was terrifying and probably premature, but staying in that exploitative system would have destroyed my passion before I ever got started.
Building Something Together
Going solo was liberating but lonely and expensive. Every cost fell on my shoulders: materials, equipment, studio space, marketing, everything. As a young designer with no established client base, it was financially crushing. I could barely afford to create, let alone showcase my work.
That’s when an idea formed: what if we didn’t do this alone? What if young designers shared costs, shared resources, and built something together?
From that thought, the Australian Fashion Exchange (AFX), the first fashion cluster in New South Wales, was born. The concept was simple: pool our resources, share expenses, and create opportunities that none of us could access individually.
Together, we achieved things that seemed impossible alone. We showcased at Australian Fashion Week. We exhibited at the QVB. We gained visibility and legitimacy as a collective.
Going solo was liberating but lonely and expensive. Every cost fell on my shoulders: materials, equipment, studio space, marketing, everything. As a young designer with no established client base, it was financially crushing. I could barely afford to create, let alone showcase my work.
Read More
That’s when an idea formed: what if we didn’t do this alone? What if young designers shared costs, shared resources, and built something together?
From that thought, the Australian Fashion Exchange (AFX), the first fashion cluster in New South Wales, was born. The concept was simple: pool our resources, share expenses, and create opportunities that none of us could access individually.
Together, we achieved things that seemed impossible alone. We showcased at Australian Fashion Week. We exhibited at the QVB. We gained visibility and legitimacy as a collective.
But success came with lessons I wasn’t prepared for. I was young, passionate, and completely absorbed in building the business. I worked days in a row without breaks, determined to stay on top of everything. I was doing too much solo work, handling too many aspects personally, driven by the belief that if I just worked hard enough, everything would work out.
The lesson I learned came brutally: manage your risk. Watch your cash flow. Build a proper team. I was so busy creating, producing, and pushing forward that I failed to follow up on payments. Our cash flow dried up. The company went bust. We had to close everything.
I lost everything. The house. All the income. Everything I’d built.
It was devastating. But in that devastation, I learned the most important lesson of my career: start small and grow organically. Manage risk within your means. Ambition is essential, but sustainable growth is what keeps you alive in this industry.
But success came with lessons I wasn’t prepared for. I was young, passionate, and completely absorbed in building the business. I worked days in a row without breaks, determined to stay on top of everything. I was doing too much solo work, handling too many aspects personally, driven by the belief that if I just worked hard enough, everything would work out.
Read More
The lesson I learned came brutally: manage your risk. Watch your cash flow. Build a proper team. I was so busy creating, producing, and pushing forward that I failed to follow up on payments. Our cash flow dried up. The company went bust. We had to close everything.
I lost everything. The house. All the income. Everything I’d built.
It was devastating. But in that devastation, I learned the most important lesson of my career: start small and grow organically. Manage risk within your means. Ambition is essential, but sustainable growth is what keeps you alive in this industry.
Starting Over
After losing everything, I could have given up. Many people would have. But that burning desire, that calling I felt from day one in fashion school, wouldn’t let me quit. I had to keep creating. I had to build something.
I started with what I loved: my own label. I launched a small women’s wear collection, focusing on luxury pieces with leather, interesting prints, and unique designs. Because we manufactured locally in Australia, the pricing was high, too high, as it turned out, for most local stores. Getting retailers to stock my pieces became an uphill battle.
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So I adapted. I travelled overseas, working directly with offshore manufacturers to learn their processes and understand how to produce quality at more accessible price points. During this exploration, I noticed a gap in the market: made-to-measure for women. At that time, most women’s fashion was ready-to-wear with limited sizing options.
The concept of custom-fit garments tailored to individual measurements wasn’t widely available.
I pivoted the entire business model from ready-to-wear to made-to-measure for personal clients.
Without a studio at this point, I adapted again. I travelled to clients’ office spaces and homes. Sometimes clients came to my own home. It wasn’t conventional, but it worked. I was building relationships, creating custom pieces, and slowly rebuilding what I’d lost.
Then something unexpected happened: a few of my female clients asked, “Do you also do menswear?” I started small, just a few custom shirts.
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But the menswear requests kept growing. Shirts led to trousers. Trousers led to full suits. Vests. Complete formal wear. The menswear side of the business grew faster than women’s wear ever had, and I found myself more in control, better able to understand and meet customer needs.
We reached a decision point: we couldn’t do both well with limited resources. We put all our budget into growing one category and committed fully to menswear.
It felt like finding my niche within my niche. This was where I belonged.
The Apartment Studio
As the menswear business grew, driving to clients became inefficient. I couldn’t deliver the level of quality and service I envisioned while working out of a car and conducting fittings in clients’ homes. I needed a studio. But I didn’t have the capital for proper commercial space.
So I did what any obsessed designer would do: I converted my apartment into a studio. The living room became the showroom. The dining area became the consultation space. Storage, fabric cutting, sewing machines – everything filled the apartment. I lived in just the bedroom.
It sounds crazy now, but at the time, it was the solution that let me deliver quality service while keeping costs manageable. Clients came to my apartment-studio for consultations and fittings. It was intimate, personal, and honestly, a bit unconventional, but it worked.
Of course, nothing is perfect. We had to be quiet after certain hours, which meant all machines had to shut down in the evening. When multiple clients came for appointments, the space got cramped quickly. The apartment had no air conditioning; winter was fine, but summer? Trying on wool suits in a hot apartment isn’t anyone’s idea of luxury.
But we kept pushing forward. Every dollar we made went back into the business. We saved relentlessly, invested in better equipment, improved our processes, and built our reputation client by client. Word of mouth started working in our favour. Referrals increased. We were growing organically, exactly the way I’d learned we should after the AFX experience.
The Milestone
By the end of last year, we’d reached a tipping point. Referral clients were coming consistently. We were organically growing beyond what the apartment studio could handle. We needed more space, not just for clients, but for machines, for a proper workshop, and for the ability to work without noise restrictions.
Most importantly, we needed a space that reflected the quality of work we were producing. Our clients deserved better than a converted apartment, no matter how well we’d made it work.
When the opportunity came up for a beautiful studio space in St Leonards, in the area where we’d been building our reputation, we jumped on it. We took on the lease knowing it was a significant financial commitment but also knowing it was the right move.
This wasn’t just about more square footage. This was about taking Winslow to the next level. About creating an environment where clients could experience true luxury service. About having the proper facilities to expand our capabilities. About building a team, we’re now around four people and growing.
This studio represents everything I’ve learned: start small, grow organically, manage risk, invest wisely, and never compromise on quality or vision.
The Why
Here’s what I haven’t told you yet, or maybe what I haven’t explicitly said: none of this has ever been about money. Don’t misunderstand, I run a business, and businesses need to be profitable. But that’s not the why. That’s not what gets me out of bed every morning, what keeps me working late into the night, or what makes me obsess over every detail of every garment.
Inside me, from that first day in fashion school, there’s been a burning desire to create a successful designer brand and business. Not for wealth. Not for fame. Not even primarily for the clients, though I deeply care about every person who trusts me with their important moments.
This is my calling. This is my soul’s desire.
Fashion design, specifically, creating bespoke menswear that changes how men feel about themselves – this is my purpose. When a nervous groom puts on the suit I’ve created and suddenly stands taller, breathes deeper, and and smiles wider because he’s seen himself transformed, that’s not just a business transaction. That’s me fulfilling my purpose.
"Fashion design, specifically, creating bespoke menswear that changes how men feel about themselves – this is my purpose."
Winslow isn’t just a tailoring service. It’s a brand with a story, a personality, and a mission. We’re building something that will outlast trends, that will create lasting value for our clients, that represents excellence in every stitch.
When people ask how I’ve persevered through all the setbacks, the exploitation in the early years, losing everything with AFX, the uncertainty of starting over, and the years in a cramped apartment, the answer is simple: This is what I am meant to do. I am walking the path that God has created for me, and no challenge can stop me.
This is my why.
THE PHILOSOPHY
What does my journey mean for you, for someone considering Winslow for their tailoring needs? It means that when you work with us, you’re not just hiring a service; you’re partnering with someone for whom this isn’t a job or even a career. This is a calling. Every garment I create carries the weight of that 17-year journey, all those lessons learned, all those failures survived, and all that passion channelled into creating something perfect for you.
It means I care about your garment as much as you do, maybe more. Your wedding suit isn’t just another order; it’s part of my life’s work, part of building this brand, and part of fulfilling my purpose. Your satisfaction isn’t a business metric; it’s validation that I’m doing what I’m meant to do.
It means that the attention to detail, the obsession with fit, and the countless hours spent perfecting techniques – these aren’t marketing claims. They’re the natural expression of someone doing their life’s work.
- Every ounce of passion, skill, and dedication I possess
- 17 years of experience condensed into the garment we create together
- The benefit of every failure I've survived and every lesson I've learned
- A piece of my life's purpose, tailored to your body and your story
The Journey Continues
This story isn’t finished. Winslow is still growing, still evolving, still striving towards that vision I’ve carried since my first pattern-making class in fashion school. Every day brings new challenges, new opportunities to refine our craft, and new clients whose trust we have the privilege of earningThe studio is established. The team is growing. The reputation we’ve built is strong.
‘m grateful you’ve taken the time to read my story. If it resonates with you, if you’re looking for that same level of passion and commitment in the person creating your wardrobe, I’d be honoured to work with you.
-Ashan Winslow-
Founder & Creative Director, Winslow