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Get Their Look | Menswear Style Legends

For the Icons of Style Issue, we’ve picked a few men whose panache approach to dressing gave them permanent relevance within the fashion realm. It’s safe to say that menswear normally works by offering guys clothes that make them hip, but these icons run things in the opposite direction. They made the clothes cool. In their own unique ways, they embody the wise words, “Know first who you are, and then adorn yourself accordingly.” Read on below to see some of our favorite style moments and how to achieve them.

Pablo Picasso

Icons of Style laydown pablo picasso

As one of the greatest artist of the 20th century, Mr. Pablo Picasso undoubtedly knew a thing or two about making a visual impact. Whether he was wearing bright red, two-tone shoes, or one of our favorites shown above, bold checks vs. stripes, he was comfortable with himself. His style is just as inspirational as his art and he could switch from unexpectedly formal to “artistically slouchy” as quickly as he changed his painting style. 

John F. Kennedy

John F Kennedy Icons of Style for ONS Clothing

We look at JFK’s impeccable taste as inspiration for American elegance, and confident carefree simplicity. It wasn’t always so much about the clothes, but more about his unselfconscious attitude. He definitely had the cool factor, but that’s not to say we can’t learn a thing or two from his style. Born in the suburbs of Boston, Ivy League style, was his go-to style and he wore it well. To quickly sum it, up we say softened suits, sweaters, and unexpected trousers, with a particular eye for color.

Sidney Poitier

Sidney Poitier Icons of Style

Mr. Poitier became the first black man to win an Oscar for Best Actor. He won at a time when he was incredibly politically active, and his daily uniform consisted of an impeccably tailored slim black suit, a crisp white shirt, and a tie. On casual days, he was no less elegant, paying attention to detail every single time. In these times of streetwear and heavy athleisure trends, the lesson here is, it’s fine to dress in a more formal manner even if it’s on a daily basis.

Ernest Hemingway

Icons of Style Ernest Hemingway

Once described as a “magnificent, broad-shouldered man” we all know Mr. Hemingway as the pioneering influential author of the 20th century. Literary work aside, his hyper-macho, rum-drinking, bull-fighting, boxing (he was known to challenge potential acquaintances to a boxing match), and over-the-top personality was known to be…a lot. With a personality like that, his style provided a healthy balance of practicality, comfort, and elegance. If you’re going to challenge someone to a boxing match, you might as well look good and be comfortable doing it.

If you liked this story, check out more in our Urban Transplants issue.


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