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I’ve written about the advantages of buying quality over quantity before, but I wanted to illustrate the point further using an example from my personal experience.

This black leather jacket by Ralph Lauren Purple Label is my favorite piece in my entire wardrobe. I paid $600 for it seven years ago. It was on clearance at the Ralph Lauren outlet at Woodbury Commons in upstate NY (I used to take the bus there every month to stock-up on items for my college eBay hustle – but that’s a story for a different day). The original retail value was $4,200.

Not only is the fit perfect and the lambskin butter soft, but over the years this simple bomber jacket has become a sort of urban legend among my group of close friends. One of my boys dubbed it “the piece”. And when “the piece” gets broken out, that means it’s going to be a good night – or at least a long one.

The thing is, when I wear this jacket, I feel like a million bucks. It’s like a piece of armor; I walk taller with it on and feel damn near immortal. It’s also like an old friend, full of incredible memories from the past seven years.

Here’s three stories that illustrate the power of a beautiful investment piece:

Show Stopper 

2008. I was at a comedy show in the LES years ago (sitting in the front row, like a rookie) and the comedian improvised a series of jokes that started with this jacket. He started with something like “Damn Whiteboy, that’s a fly leather jacket…(looks over at my date)…you’re not with him for him are you…you’re with him for that fine leather”. We all laughed. Later that night he invited us backstage to hang with the other comedians. 

Real Recognize Real

2010. I was stopped in the street in NYC by a sharply dressed older gentlemen who asked my wear I got the jacket. We got to talking about menswear, took each other’s contacts, and kept in touch. Later he became my first client for personal styling/shopping and eventually introduced me to my first custom tailor, which changed my life.

Velvet Rope Mover

2013. This tough-nose bouncer wouldn’t let one of my friends into the club because he was wearing a t-shirt and sneakers. Inspired by how we used to sneak into movie theaters as kids, I went inside with my other friend, we both got stamped, and I sent him back outside with “the piece” off my back. Our t-shirt wearing friend put the jacket on and slid right by the same bouncer fifteen minutes later. Then somehow he convinced me to keep the jacket for the night…and it turned out to be an epic one for him. Now he wants to wear the piece every time we go out.

The moral of the story: when it comes to classic pieces like a black leather jacket, don’t buy cheap. Think long-term investment.

  • Quality generally fits better (thanks to years of pattern development, research, and trial & error sampling)
  • Quality looks and feels better every time you wear it. And you will wear it more often…I wear this jacket roughly three times a week
  • Quality lasts longer, which can save you money in the long run
  • Quality only gets better with age. This jacket has been in some tough spots over the past seven years, but it still looks fantastic
  • Quality can serve as a memento that sticks with you over the years. When you look back at one of your favorite pieces, you will be reminded of some of those unforgettable moments
  • Quality can be passed down, so you can watch your children enjoy similar memories
  • Quality can give you confidence and make you feel like a better man. This can be a priceless transformative feeling
  • And, of course, quality doesn’t have to be ridiculously expensive. Anything can be found on sale if you know where and when to look


I’m not saying everything in your closet has to be (or should be) high quality – I’m all about the high/low mix. But when it comes to wardrobe staples, like a black leather jacket, there are several reasons to invest in a keeper.

Do you have a go-to “investment piece” in your wardrobe?

Thanks, as always, for reading.

Yours in style,

Dan Trepanier