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In the last three years of my #menswear journey I’ve learned a lot about how to build my wardrobe from both personal experience and those who are much farther ahead. I have summarized these into bite-sized pieces for those starting to put more effort into dressing better or those clueless on how to move forward. Think of these lessons as a practical guide to wardrobe building.

1. Build your wardrobe around the places you frequent and lifestyle you lead.

I live in the city, spend most of my time in an office, occasionally visit a nice restaurant or bar and attend social gatherings – in short, urban and cosmopolitan. I’ve built my wardrobe around that notion and it keeps my spending focused. This means I have more dress and sport shirts than polo shirts, more chinos than jeans, and more dress shoes than sneakers. Dress according to where you go and what you do most often, and add items to your wardrobe that will help you fit in.

2. You don’t become well-dressed overnight.

Men’s magazines like to prescribe the “top 10 items a man should have in his wardrobe”. They make it sound easy and effortless but it couldn’t be farther from the truth. It takes real courage to dress better and get over the fear of being ridiculed by peers. It takes time to find out what look/brand/tailor/fit works and what doesn’t. It’s not just about wearing a suit but rather being confident and comfortable in one. These things don’t happen overnight so take it one step at a time, slowly but surely.

3. Start with inexpensive basics and upgrade them over time.

When starting out make sure you’re adequately stocked with inexpensive basics. As you start buying more expensive items, like shoes, you don’t want to wear out a nice pair too soon. Once you have two to three pairs of inexpensive shoes you can start buying expensive pairs to slowly replace the old ones that are most likely reaching the end of their lifespan. Apply the same strategy to everything else in your wardrobe.

4. Don’t forget the big picture.

It’s easy to get carried away buying small items like ties and pocket squares. It’s also easy to get carried away buying a cult brand that comes up on your radar. I’ve been down this road before and it’s easy to lose focus when you’re constantly being bombarded with the latest and greatest. However, do not be distracted by the trees and focus on the forest. The goal is to be well-dressed and have a uniform, not someone who has a large collection of ties and pocket squares or the latest piece.

5. Use an inexpensive item to see if the look works then buy the real thing.

Often times it’s hard to justify an expensive purchase when you’re not sure of how it will fit into your wardrobe or if you’ll ever use it as often as you think you’ll do. I recommend starting out with something that looks relatively the same yet won’t blow a hole in your pocket. When you’re sure that it fits into your wardrobe and you’ll actually use it then by all means get the real deal.

6. If you’re having a hard time with ready to wear clothes try bespoke.

There has never been a better time to buy ready to wear clothing. There are plenty of brands each with multiple fits that are constantly being tweaked to meet the demand of consumers. However, if you don’t fit into the theoretical average then the only recourse is to go bespoke. There are plenty of tailors in the Philippines that can make shirts, suits and trousers for a reasonable price.

7. Bespoke is not for everyone.

It seems like I am contradicting myself but I assure you I am not. It takes a different kind of person to appreciate bespoke. You’ll need to understand a bit of everything: cloth, cut, fit, proportion, and style. You’ll need the patience for multiple fittings. You’ll discover that the first shirt you had made is less than perfect but you accept it anyway knowing it’s never perfect the first time around. Bespoke is not for everyone but it is very rewarding.

8. Do your homework.

No one likes doing homework but it has to be done. There are plenty of books, blogs and forums out there of those that have been down this road before. Use this accumulated knowledge to avoid making the same, usually costly, mistakes.

9. Buying better is not the same as buying luxury.

I recall the story of a friend who told me that the soles of his shoes were separating from the uppers after a few years of wear. They were expensive but nonetheless held together by glue. This meant that sooner or later it would fall apart compared to shoes stitched together. This is a good example wherein buying better does not mean buying luxury. What you’re actually paying for is the design and exclusivity—not the construction. Of course there are a few exceptions to this but much harder to discern when many of the great, previously low profile brands were bought up by major players in the luxury business.

10. Paying more doesn’t always mean it will last longer.

I bought my first pair of Japanese selvedge jeans in August 2011 and stopped using them in January 2014 when I saw that the hip area was thinning out. Looking back it would seem that I paid too much for a pair I wore for two years and five months. But it’s not about having a longer lifespan. In the case of jeans it’s about owning a pair made using vintage machines and better materials. It’s nice to have these items in your wardrobe but don’t expect them to last longer than average especially clothing.

I welcome discussions over email at kevin@bespokemanblog.com.