Quality Menswear: An Investment for Life

June 29th, 2014


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 much more than forty two hundred. 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?

Yours in Style,

Dan Trepanier

Shop Custom Menswear Made in America


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  • Chris

    Today, while strolling downtown in Toronto, I think I hit the “motherload”. I found a vintage A-2 US army bomber jacket, made in the USA. The dark brown was exactly what I wanted and the fit was PERFECT. I immediately sent it to drycleaning but when I get it back, I expect to have similar experiences as this article. And I relate perfectly to the notion that this jacket makes you feel like a million bucks. Just has that vibe to it.

  • R_Theriault

    Hey Dan, great article and great jacket! Is it possible to get some further information and photos of that jacket? Since it is 7-8 years old, the only hope of finding it is via the secondary markets such as eBay or Craigslist. Can I contact you directly via email? If so, let me know how.

  • Sergio Arteaga

    Definitely have to go with my first bespoke suit on this one from MAB.

  • http://www.lucidlingo.com.au/ Gazman

    Many men spend oodles on individual items of clothing on the premise that quality is the key. In the main, I agree. But there is one factor that pours cold water on this approach: our changing body shapes and changing lifestyles. Spending $1K on that in-vogue brand blazer may seem like a good investment but after a season on the weights machine it’ll soon be on eBay or the back of the closet. Likewise, spending large sums on $200 dress shirts for work may seem a good choice at the time, but not so good when you jack in that job in the sharp end of town for one as a hobby-farmer.

  • Jeff P.

    I have a bomber jacket that gets a ton of compliments. It’s not buttery smooth like Dan’s purple label piece, but it’s still one of my favorites. I wore it during the November 2013 TSB Giveaway, and it scored me in the top 10!
    Can’t wait until fall comes so that I can wear that thing again!

  • Francis

    My grandpa gave me his pair of 1980’s RM Williams boots a few years ago as the leather soles became a little to slippery for him in his old age. I have worn them at least weekly ever since. RM’s have had a massive resurgence in the past couple of years in Aus and as mine differ to those newer models around me I am forever being asked when I got them and if I picked them up on sale? When I tell them they are more than 30 years old they are amazed at how long they have lasted and how great they still look. A friend of mine even surprisingly conceded that they came up better after a polish than his 6 months old pair. Myself of course with the knowledge of the “gets better with age” principle, maybe a little less surprised.

  • Oisik

    “sharply dressed older gentlemen who asked my wear I got the jacket.” – Typo! Should be “me where”

  • Preston

    Love the stories Dan. TSB is much more than the aesthetic appeal; it’s the rich history of your clothes in relation to the world around you, told in great editorial fashion.

  • Stuart

    It’s great to hear the stories behind these pieces. It makes the connection to the menswear lineage that much more authentic.

  • Harrison Krupnick

    Do you have any suggestions of where to get a jacket like this? I hear great things about Schott but all their jackets are quilted lined and probably a lot heavier than yours. Great post by the way!

  • Juan

    This is one of my favorite articles as well. I love hearing about the history of a particular clothing item and the stories that go with it, as, for me, that’s what it’s all about, i.e. the relationship you build with your wardrobe and the experiences you share with it.
    Buying quality means you can share years, maybe even your whole life, worth of experiences and great stories with your clothes and, ultimately, isn’t that what we are all looking for?
    My first tie was given to me by my dad when I was seven years old. It’s a vintage Dior tie from the late 60s that my dad no longer used at the time because it had gotten too short for him (he always ties a full-Windsor). I had never handled silk at the time, and I remember how luxurious and fascinating the whole process of tying such a soft piece of clothing felt. I still wear the tie regularly 15+ years later, the silk is still as soft as ever even after 40+ years of wear, and every time I wear it I get this same thrilling sensation in my chest.
    More recently, thanks to TSB, I decided to pull the trigger on some burgundy tassel loafers from J&M. They were 350+ euros (no thrift stores over here sadly), but these beauties are made in the US and the quality is just something I have never experienced before, even in “quality” footwear supposedly made in England.

    • http://www.TSBmen.com/ Dan Trepanier

      YES!! Couldn’t agree more.
      Thank you for sharing Juan.

  • Harrison G

    Great piece dan. There really is something magical about that first true investment piece. My dad gave me his sickness for fine clothes by finding me a perfect sport coat years ago. We had searched for quite a while that would fit my build (rugby prop doesn’t equal easily sized). He found a gorgeous zegna sport coat for 300 (from 2 grand) and bought it without me. Sure enough fit perfect then, fits perfect now. Every time I slip it on I feel great and think of my dad.

  • Herbert Morrison

    I was threatened for merely joking about jacking that jacket. True story.

    • http://www.TSBmen.com/ Dan Trepanier

      #Truth I’m down to go blow for blow for this thing

  • http://Keyboardandcompass.com/ Jeff McAllister

    Great post, Dan! Owning a beautiful piece is one thing. But ultimately, what makes a garment special are the stories you share with it.

    • http://www.TSBmen.com/ Dan Trepanier


  • Massimo

    Mine is a Ferragamo carmel colored leather jacket I snagged at The Mall Outlets just outside Florence, Italy about ten years ago I would guess. I believe I paid about $500 for it (retailed for several thousand). I get compliments all the time, and they come from people that recognize a fly jacket. Sadly, it is somewhat delicate, so cannot be worn too often, but it gets enough play to stay fresh.

  • http://www.vitamincm.com VitaminCM

    $600 seems fair for that jacket, but $4,200 is a typo right? Do you have the names of anybody who paid full price? I have a pet rock I wanna unload.

    • TO

      I bet there is an extreme difference between a retail $600 leather jacket and that beauty. Not saying that the $4200 is fully justified though, it is simply insane.

    • http://www.TSBmen.com/ Dan Trepanier

      No reason to throw rocks. Prices are all relative. I’ll never forget seeing a fur-lined vicnua overcoat that sold for $110,000 at the Bijan store on Rodeo Drive… In the words of Meek Mill: There’s levels to this shit

      • Drew

        I was being a nice son once with my mom when we were up hiking in the North Carolina mountains and went shopping with her in the town of Highlands, which for whatever reason, has some really upscale shopping. My mom was in a shop with pretty expensive stuff on one side, and ridiculously expensive stuff on the other side. I saw a women’s fir jacket going for 75,000 dollars. I went back and checked like three times because it just seemed insane. Surely it was 7,500 right?? Nope, 75,000.00 was the price. Unreal. But you’re right man, it’s all relative. Clearly someone finds that worth it

  • TO

    Unbelievable! Honoured to have been apart of one of the many illustrious nights of this jacket! This is one of my favourite articles ever. Feeling more inspired than ever to scour for my own big time investment pieces, starting I think with a leather piece !

    • http://www.TSBmen.com/ Dan Trepanier

      Thanks TO! When I was writing this, I wasn’t thinking “best article ever”. Means a lot coming from you my man. Cheers.