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


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