How to Dress Like. John F. Kennedy

His legacy is one of contradictions and dichotomies.  His Presidential victory was seen by many as a socio-political mandate, yet it was one of the smallest margins of victory in American history.  He was an archetypal symbol of virility with chronic back problems and serious medical issues.  There is the family man, and the presumed extra-marital affairs.  There was his slim-cut, dark, two-button suit in the White House and his rolled up khakis, un-tucked shirt and Wayfarer sunglasses in Hyannisport.

Yet, for all this, his impact on American style bears no question.  Hs sartorial standards have become commonplace in the vocabulary of American fashion.  His hatless appearance, at the 1961 inaugural, was a watershed moment, and summoned a resounding death knell for men’s headwear - from which it has yet to recover.  The two-button suit, he favored, has become a timeless staple of the Americana wardrobe (Brooks Brothers introduced the two-button “Fitzgerald” suit in 2007).

But it is not so much in what he did or did not wear, but rather how he wore it that made his style memorable.  It was confident and unself-conscious.  His sartorial gestures seemed effortless.  “The ease of his style made it really look like he didn’t think that much about it,” says men’s fashion designer Thom Browne (Brooks Brothers Black Fleece).

The following are some examples of how you may come to have such an effortless silhouette, regardless of budget.