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The current menswear obsession of not looking obsessed with our clothes – sprezzatura – is not a new thing. The attempt to be intentionally nonchalant has been with us for decades, as this 1940 Stetson ad proves. Seventy-five years ago, as the 1930s and the “golden age of menswear” were coming to an end, guys were already concerned with “carefully studied casualness,” looking lived in and laid back without looking like they tried. Interesting too that it’s called a “trend,” as it is now. And to be honest, I understand the sprezzatura motivation. Dressing well can sometimes look stiff and formal, especially today in our very, very casual world. Equally important is that you want to look like you are wearing your clothes, not the other way around. And so buttons are left undone, shoe straps unbuckled, hats bent out of shape. All to show personality and uniqueness. But to do this intentionally is to betray, in my opinion, the goal you are seeking. You cannot be at once aware and blissfully unaware of what you are wearing. READ MORE

The current menswear obsession of not looking obsessed with our clothes – sprezzatura – is not a new thing. The attempt to be intentionally nonchalant has been with us for decades, as this 1940 Stetson ad proves.

Seventy-five years ago, as the 1930s and the “golden age of menswear” were coming to an end, guys were already concerned with “carefully studied casualness,” looking lived in and laid back without looking like they tried. Interesting too that it’s called a “trend,” as it is now. And to be honest, I understand the sprezzatura motivation. Dressing well can sometimes look stiff and formal, especially today in our very, very casual world. Equally important is that you want to look like you are wearing your clothes, not the other way around. And so buttons are left undone, shoe straps unbuckled, hats bent out of shape. All to show personality and uniqueness. But to do this intentionally is to betray, in my opinion, the goal you are seeking. You cannot be at once aware and blissfully unaware of what you are wearing.

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Many years ago I backpacked through Europe with a girlfriend (who is now my wife). Along the way we stopped in the Scottish town of Loch Lomond. One night, we headed down to the pub for a pint and happened to catch some live traditional music. Near the end of the evening, the band played the town’s eponymous song. My wife and I were surprised to discover that we knew all the words, by heart, even though neither of us remembered ever hearing the song before.

L.L.Bean Boots are my sartorial version of the Loch Lomond song. I bought my pair a few years ago and I don’t really remember how I choose them. I was in need of rain boots and instead of just regular rubber versions, somewhere in my subconscious was this image of those slightly old-timey, Ivy League-style boots. I even knew they were called Bean Boots despite the fact that no member of my family or group of friends ever had a pair.

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