In 2007, I faced a challenge that would teach me invaluable lessons about building a wardrobe: I needed to test bespoke tailors and find reliable partners for my fledgling business. The solution? I set out to buy 20 custom suits in 10 days.
This wasn't a vanity purchase or a fashion experiment—it was business research. I traveled to Hong Kong, Bangkok, London, and New York, meeting close to 100 tailors to find the right partners. It was intense, expensive, and surprisingly educational. Looking back over the nearly 20 years since, I can distill that experience into five critical lessons that apply whether you're building a custom wardrobe or buying ready-made clothing.
Lesson 1: Your Style Evolves—Invest in Classics
Here's the brutal truth: of the 20 custom suits I bought in that whirlwind 10 days, only 2 are still in my wardrobe.
I have the receipts. I spent the money. Yet nearly 90% of those suits have been discarded. Why? My style evolved. The suits I chose in 2007 don't represent the man I am now, nor do they reflect what I've learned about timeless dressing.
The two that survived? Navy blue and charcoal grey, both solid colors, both classic cuts—nothing trendy, nothing fashion-forward. The suits I thought were unique at the time? Many featured fabrics, patterns, or details that seemed brilliant in the moment but looked dated within a few years.
The lesson: Stick with classics. A solid-colored, single-breasted, two-button suit in navy or charcoal will work whether you're 20, 40, or 60. Trends come and go. Classics endure.
When building a wardrobe—whether custom or off-the-rack—prioritize timeless pieces over fashion-forward details. You'll thank yourself in five years.
Lesson 2: Time Saves Money—Give Yourself Space to Negotiate
I didn't have time to negotiate. I was on a mission, moving from city to city, meeting tailor after tailor. So I paid close to full retail price for most of my suits.
Some tailors claimed they were giving me deals because I represented a potential business partnership. Others charged me double the price of their competitors for nearly identical work. I had no leverage and no time to shop around.
The lesson: If you have time, you can build an exceptional wardrobe for a fraction of the cost. Time is currency in the world of clothing.
- Give yourself weeks or months to find the right tailor rather than days
- Shop for sales and discounts; patience reveals better deals
- Build relationships with tailors and clothiers; they'll often negotiate better rates for repeat business
- Thrift high-quality vintage pieces that have already proven their staying power
Conversely, if you need a custom suit in two weeks, expect to pay a premium. Urgency always costs money in bespoke tailoring.
Lesson 3: Less Is More—Avoid the “Kitchen Sink” Suit
I made a critical mistake early on: I tried to incorporate every detail I'd learned about suit design into single garments. Slanted pockets on striped fabric with peak lapels? Sure, let's try it. A bold pattern combined with multiple construction details? Why not?
The result was what I call “Frankenstein suits”—interesting in concept but awkward in reality. I was throwing too many spices into the pot and creating a mess.
The lesson: Simplicity is sophisticated. The best suits are built on classic silhouettes with minimal embellishment. When you add too many details, you confuse the eye and date the garment faster.
A well-tailored suit in a solid fabric with a classic cut will always outperform a trendy suit packed with details. Master the basics before experimenting with advanced design.
Lesson 4: Get Expert Advice, Not Salesman's Advice
I assumed that successful tailors would automatically be good at giving style advice. I was wrong.
The tailor industry (like most industries) has specialists: salesmen, tailors, and designers. The best are rare combination of all three. What I found instead were:
- Salesmen who prioritize making a sale over giving good advice
- Master tailors who can execute beautifully but don't understand classic style or proportion
- Designers who sell interesting ideas but charge premium prices without delivering premium construction
Finding someone who combines all three—excellent sales acumen, superior tailoring skills, AND a deep understanding of classic design—is rare. When you find them, they become invaluable.
The lesson: Before trusting a tailor or clothier with your wardrobe, verify their credentials. Ask to see finished suits. Check their understanding of classic proportions and silhouettes. Don't take design advice from someone whose primary job is to sell you something.
Lesson 5: Work with the Best When You Can Afford It—It Saves Time
I visited legendary tailors like Narin Couture in Bangkok, W.W. Chan in Hong Kong, and tailors on Savile Row in London. I also discovered talented tailors in Chiang Mai and Kowloon who charged considerably less.
The difference? The established masters consistently delivered on all three fronts: excellent sales service, expert design guidance, and flawless tailoring. The underdiscovered gems sometimes offered amazing quality, but they often had communication barriers, language issues, or scaling problems that made long-term relationships difficult.
I found one exceptional tailor in Kowloon who spoke only Chinese. Working through a translator would have required constant effort and created margin for error. There was a reason he hadn't scaled his business—the communication barrier that saved him money was the same barrier that made him difficult to work with.
The lesson: If you can afford to work with established masters, do it. You pay for their expertise, communication skills, consistency, and reliability. These things save you time in the long run, which has real value.
However, if you have more time than money, diamonds in the rough exist. Just be prepared to invest your time in communication and management.
Building Your Wardrobe: The 20-Year Perspective
Looking back at that intense 10 days in 2007, I learned more through mistakes than I would have through perfection. Those 20 suits taught me that wardrobe building is a marathon, not a sprint.
The two surviving suits remind me daily that classic, well-made pieces compound in value over time. A timeless suit serves you for decades. A trendy suit is outdated in years.
Whether you're investing in custom bespoke or building a wardrobe from quality ready-made pieces, these five lessons apply:
- Prioritize classics over trends
- Give yourself time to make good decisions and negotiate better prices
- Keep designs simple and elegant
- Get advice from true experts, not salesmen
- When possible, work with the best—time has real value
Start with these fundamentals, and you'll build a wardrobe that lasts.
Watch: 5 Lessons Learned Buying 20 Custom Suits in 10 Days
For more on building a quality wardrobe, read our guides to buying suits and building a timeless men's wardrobe.
