Letters from the Old World

Letters from the Old World

$50 vs. $300 Shoes, Explained

Never fall for a “bargain” again…

Evan Amato's avatar
Evan Amato
Feb 06, 2026
∙ Paid
All photos by Raphael Barberi.

I was at the beginning of my menswear journey when I first moved to Italy. Going into the mall, I’d see “100% Italian leather shoes” being sold at ridiculous prices, often as low as 40 to 60 euros. “Why do they cost so little?”, I’d ask. “Are tariffs really that high back home?”

No, dear reader, they are not.

So how is it, then, that someone can sell “100% Italian leather shoes” for such a low price? To put it in Orwellian terms, the answer is that “all leather shoes are equal, but some are more equal than others”. There are real differences between high and low quality footwear, and they’re about more than just the type of leather used.

Once you learn what makes one pair “more equal” than others, you’ll never opt for its less-expensive counterpart again. Today, I break down the five main differences between a $50 and $300 pair of leather shoes, and prove why the latter are more than worth the investment…

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