Menswear Items that Get Better with Age

June 16th, 2014

It’s good to be a man.

After all, it’s a man’s world (although it would be nothing without a woman or a girl).

The best part is, if we stay healthy and well spirited we can get more attractive with age. Grey hair, wrinkles, rough experienced hands…all things that are often considered sexy as we ease into our mature years.

Naturally, menswear follows a similar pattern. As men we don’t need to shop for the latest trends, or re-invent our style based on the current season. Instead, we can invest in staple pieces and wear them for years – sometimes decades – and they only get better as they take on their own worn-in character and “experience wrinkles”.

Not everything looks more attractive with wear & tear, but here are some items that certainly do (in my opinion, as always).

Raw Denim


These are Alex’s jeans. They were dark indigo blue (almost black) when he first bought them five years ago, now they have all kinds of cool whiskering. You can see where he keeps his Iphone…which is not only a conversation starter but also a representation of his character – because if you know Alex, you know he stays close to his Iphone, and his Reddit community.

Leather Jackets


I bought this jacket in a vintage store in Montreal. I almost didn’t drop the $250 on it, but I’m so glad I did; it’s become one of my favorite pieces. It’s not a typical calf or lamb skin, this thing is cut from hardcore belting leather. It was probably stiff as a board when it was new. To my unborn son: this will be yours one day, when you pry it from my cold dead hands.

Rugged Boots


These are combat boots from the 1960s. Just looking at them makes me daydream about the men who wore them, and what heroic things that were doing with them laced halfway up the shins.

Workwear “Chore” Jackets


This is my father’s old shop coat from his 30+ years working at the Chrysler plant in Windsor Ontario. It has sentimental value to me as it truly represents my father – the hardest working man I’ve ever known and a daily inspiration to his three sons.

Leather (or Canvas) Luggage


Why drop $800 on a handmade duffle bag from a craftsman like Frank Clegg? 1) Because you’re supporting an American doing world-class work 2) Because you’ll never have to buy another one in your lifetime – which will ultimately save you money in the long run

Denim Shirts (or Jackets)


This one is kind of cheating, but I love the concept and wanted to share it. Sarah and Cody of Totally Blown in Joshua Tree California are taking a unique approach to apparel design. They source USA-made vintage clothing and creatively destroy it using unusual methods. This vintage denim shirt, for example, was dyed, bleached and put on a mannequin in front of a firing squad that riddled it with hundreds of gun shots. That’s not pilling you see, those are tiny bullet holes.

Canvas Sneakers


Canvas sneakers like Chuck Taylors and Vans look kinda cheesy brand new. So don’t baby them, or clean them… My homie ShoScott, born and raised downtown NYC, takes it a step further. He collects Jordans but can’t stand them looking too new. The first time he puts on a fresh pair he literally steps all over them – right foot stomping left, left foot stomping right. It’s a fascinating thing to watch, considering their price tag and the psychology behind not wanting to have the ever-sought-after “Fresh Js”.


Do you have pieces in your wardrobe that are old but looking better than ever?

Please share in the comments below.

Yours in style,

Dan Trepanier

Shop Custom Menswear Made in America


Take me to the Shop

  • Tyler

    Those aren’t combat boots from the 60s.

  • LouCaves

    I have a couple of items but the one that I want to highlight is my twelve year old leather motorcycle jacket. I bought it new and it came without a label.

    On the inside its pitch black. But because of riding ~70k miles in the sun, rain, wind and some snow the outside is dark grey/grey. It’s about 10-15 pounds, I don’t even know but it’s heavy!

    Thanks, TSB

  • Unseen Flirtations

    I have a kenzo tie from almost a decade ago that started to get noticeable wear a few years back. I thought it was gone until I thought screw it, and kept it in rotation. With extra wear and tear, slight fraying, rubbing and some little kinks in the silk, it has genuine character.

    I’d never have thought a tie could get better with age, but there you go.

    Also, leather belts. The more weathered the better.

    Great post btw. Thanks!

  • Stuart

    My favorite piece has to be a Harris Tweed jacket that I picked up for $13 at the thrift shop. With some minor tailoring, it became a thing of legend in my wardrobe.

  • JM

    one cool thing is that regular processed denim will fade just like raw denim, albeit very, very slowly. working on a pair of 508s that are starting to whisker and fade after 6 months of continous wear w/o a wash.

  • Changingman

    I’ve had a couple of black Carhartt jackets that I wore for about 8-9 years each. In high school i had Dr Martens that i wore every day for a couple of years. My current Levi’s 508 are starting to fade and wisk nicely after about a year and a half.

  • face

    Along the same lines as luggage,most leather work bags/satchels age timelessly. I bought this one about 7 years when I was a poor law school student hoping that by the time I stepped into a courtroom, my tried and true, war-torn satchel of knowledge would distract more experienced litigators from my smooth, rosy red cheeks. It didn’t. So I grew a beard and THAT’S what’s up! My suggestion – absolutely, positively invest in a nice, classic, leather bag for work and unless you’re Mark Wahlberg or James Franco, a badass beard can be a powerful, unique and timeless “menswear item.” Great job as always guys.

    • Dan Trepanier

      Agreed on the beard!

    • LouCaves

      ¡Viva la barba!

  • Jeff McAllister

    I’m luck enough to travel a ton and I take advantage of this by packing garments I’d like to be part of that story.

    Sometimes the yield is a gorgeous piece of wearable art: like these six-year raws with 30 countries worth of fades. Other times all I get is a prematurely worn out rag like this oil-stained pair of chinos I wore for 8 months straight while backpacking from Indonesia to Bangladesh.

    Some clothes are meant to last, some aren’t. The most important thing is that you have fun while wearing them.

    • TO

      That’s pretty awesome! If I end up doing a world trip I would consider traveling with one new pair of raw denim now

      • Jeff McAllister

        You won’t regret it man! Just make sure you start somewhere a bit more cool! There’s nothing worse than sliding on a pair of 14.5 ozs during summer in Vietnam!

    • Mark Smith

      Indonesia to Bangladesh is some trek. Menswear aside, what route did you take?

      Also, as a chemistry student who worries about being stuck in a lab and not seeing the world when he graduates – cheers for the inspiration!

      • Jeff McAllister

        I took a pretty non-linear route since I wasn’t too keen on applying for my Indian Visa abroad: Indonesia -> Thailand -> Laos -> Thailand -> Cambodia -> Thailand -> Myanmar -> Bangladesh with a side trips to Nepal and Sri Lanka in between. Ironically, I’m now planning to head back to school (and likely a lab for a bit.) I think a balance of is necessary!

        Also: There are plenty of opportunities to travel with a chemistry degree. Especially in energy, industrial and materials science.

      • Dan Trepanier

        Take some time after graduation my man!!! The lad isn’t going anywhere…

      • Lee Ying Ho

        Slightly off topic, but I’m a chemistry graduate and have been traveling a lot because of my job as technical service chemist.

        If you like to travel, get a job as technical service/support for a multinational company and you’ll have the opportunity.

    • Dan Trepanier

      #AMEN #WearableMemories

  • Mark Smith

    Suede boots. Okay, I get that if you’re wearing suede in a corporate/business casual environment then you should definitely treat them with suede protector and a suede brush to keep them looking sharp. But casually, let those things get beat up! I got a pair of chukkas a few weeks back which I’ve been wearing every day, and the wash on my jeans is beginning to dye the top of them blue, and I love it!

    Dillon Burke’s (’s desert boots are inspirational (

  • Galps

    I accidently spilt red wine all over my white canvas chucks whilst at a friends housewarming. Best accident ever, every time I put them on it takes me back to that night.

  • cam

    Hey guys, interesting article that got me thinking. I believe a distinction needs to be made here between things that get better with age and things that get better beat up/torn up etc. I feel many pieces get better with age but I find myself still taking care of these items. That would be my leather lace ups, leather double monks, leather Gucci loafers etc. Basically all my leather shoes get better with age because they become more comfortable but I still take great care of them. Other items would include watches, leather belts and t-shirts from high-school and college. Again these are things I feel get better with age (some for sentimental reasons) but are not necessarily “destroyed” from wear. All the best!

  • Sabir M. Peele

    That denim shirt actually looks quite appeal even though all the distressing is man-made.

  • TO

    Probably the most worn-in thing I have is a denim shirt I got in Singapore right near the start of the worldwide American ‘workwear’ craze. I haven’t even worn it that often for a while but it shows some nice wiskering. Also have some vintage Roots wheat desert boots I picked up recently that have some great staining on them and of course some beat-up Chucks.

    I had some dad jeans I grabbed vintage a year ago and was really enjoying working in even more, but I just took in the waist and seat for the second time on them due to stretching and the pockets got too angled/close together that sadly I had to retire them.

    That’s mostly it, nothing to crazy for now. But honestly I get excited at the thought of what my next future purchase might be of something that I can beat up for 10 yrs- rest of my life. And there’s nothing I’m TOO precious about.

    • TO

      I’m really intrigued by that leather jacket btw, and all these choice pieces look great. Love the shot-at shirt too, that brand actually sounds really cool (vs. more typically commercial processes of creating pre-distressed garments)