Life Lessons for the American Gentleman

What the Great Gentlemen of the 20th Century Taught Us About Being Dapper

Looking good is easy enough. Buy a fancy shirt and throw on a clean pair of pants, and you’re pretty much halfway there.  But looking dapper is an art that requires thought and personality. Over the years, a few men have stood out for their polished looks. What is it that makes their look so timelessly appealing - and what can we learn from them?

Cary Grant (1904 – 1986) defines “clean cut.” With hair parted neatly to the side to complement his angular features, he is the sort of man who would look debonair in sweats - a rare feat indeed. Grant had a formula, and he stuck with it. Pressed shirts were paired with monochromatic suit jackets: it was simple, yet effective. He didn’t follow trends, because he didn’t need to. His look was timeless; and transcended location and surroundings. Grant’s name even possesses a clipped and tidy air (a studied choice, as he was born Archibald Alexander Leach and legally changed his name). Thinking of a new vogue haircut or eccentric new fashion statement?  That’s bush league.  Real style is timeless, clean, and transcendent.  Just ask Cary.


Frank Sinatra (1915 - 1998) once sang that “you’ve either got or you haven’t got style, and if you have it, you stand out a mile.”  That was more than a lyric for Sinatra, who was notorious for always being well dressed in fine and expensive suits.  His taste was timeless, favoring tailored suits paired with conservative silk ties or bowties and fedoras. A stickler for the details, Sinatra cared about things like cufflinks and sleeve-lenghts, and where trousers should fall on the shoe line.  Undeniably suave, Sinatra left an image of a gentleman that gave a damn about putting his best foot forward, dazzling the crowds with his vocals and his style.  Sinatra’s lasting style legacy:  Stay conservative, and invest in a good tailor. 


A poet and writer with a devil-may-care attitude, Jack Kerouac’s (1922-1969) personality was contagious. His cavalier approach to life was also reflected in his clothes. He bottled up the “car ride with the windows down” look and infused it into his style. Kerouac was the Beat Generation, and his ensembles showed it. His flannel shirts fit in with the mountains of Washington with the same ease that they did in Brooklyn’s coffee shops. And Kerouac’s bomber jacket was a staple that only looked better with age - its distressed quality was tangible proof of his untamed lifestyle. Kerouac created the art of cool, and it’s a statement that isn’t going anywhere. 


Frank Sinatra once said that Ray Charles (1930 – 2004) was “the only genius in show business.”  His music and his clothes showed it. He was always hovering between a polished look and a relaxed one. His shirts were impossibly elegant - but they were always buttoned down to give off the allusion that he had just worked up a sweat (and let’s be honest… he probably had). Donning his signature black sunglasses, Charles looked dramatic with just a touch of mystery. He toed the line of slapdash style, but he never crossed it. Every poised suit had just a touch of dishevelment to it that said, “I don’t give a damn.” For the man who wants to look good without being predictable, channel Ray.

 Take the cues of yesterday’s finest gentlemen, you can craft a distinctive style that will make a timeless statement. Looking good is a man’s game.  Looking dapper is a gentleman’s style. Dress with thought, tip your hat to the greats of yesterday, and walk dapperly ever after.

 About the Author:

Jake Kaufman lives in Columbus, Ohio and writes on behalf of Bosca.

Founded in 1911, Bosca is the dream of a young Italian immigrant named Hugo.  Surviving wars and a Great Depression, Bosca continues to create luxurious leather goods that introduce the passion of Italian design to the demands of American functionality.  Find out more about Bosca by visiting their website @

  • 30 May 2013
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