Top 5 Most Stylish Presidents Of The United States

Top 5 Most Stylish Presidents Of The United States

It has probably just slipped right under your radar, but we are currently in an election cycle for the presidency of the United States of America.  Easy to miss I know.

We thought it would be fun to take a look at 5 of the best dressed men ever to hold the highest office in the land. Counting down from 5... 


5. Franklin D Roosevelt

FDR was the 32nd President of the United States (1933-1945) and the only president to be voted into office 4 times.  He is most well known for the New Deal which focused on Relief, Recovery, and Reform as a response to the Great Depression. 

While he was a generally dappered up in typical 1930s suits, hats and skinny ties. The real reason we love FDR's fashion is that he famously wore a cape to a meeting with Winston Churchill and Joseph Stalin, and totally pulled it off. That's enough to make the top 5 in and of itself.

4. Theodore Roosevelt

Theodore Rooselvelt was the 26th President of the United States (1901 - 1909).  

He is not the Father of Franklin D Roosevelt but rather a distant 5th cousin. Their closest tie was actually that FDR's wife Eleanor was Teddy's Niece...yup, FDR married his 5th cousin once removed.

But we are talking about Teddy here. Teddy was Americana before Americana was Americana.  And before it meant you were really just a hipster who despises hipsters.His love of the outdoors often showed up in his functional rugged fashions.

3. Chester A Arthur

Chester Arthur was the 21st president of the United States (1881-1885)

Arthur’s affinity for light trousers, high hats, frock coats, silken scarves and other high-fashion staples earned him the nicknames “Elegant Arthur,” the “Gentleman Boss” and “Dude of all the White House residents,”.  He supposedly owned about 80 pairs each of pants and shoes, which came in handy since he switched outfits multiple times a day, including wearing a tuxedo to dinner.

2. Barack Obama

Barack Obama is the current and 44th president of the United States (2009- Present)

He is actually the 43 person to become president since Grover Cleveland served 2 nonconsecutive terms and whoever it is that decides how to count that, decided to count those two terms as 2 presidents...? I'm slightly confused by that decision. I'm very confused by the question of who it is that decides these things.  

President Obama's perfectly tailored suits on his tall thin frame, as well as his on-trend casual wear, made Obama's fashion a topic of conversation and admiration in such menswear and pop culture outlets as Esquire and GQ.  And as with any fashion icon he was a risk taker, famously breaking with the political leader tradition of wearing exclusively dark navy and grey suits and dawning a Tan suit in 2014. But his real draw and fashion power may actually lie in his impeccably dressed better half.  Michelle is on point and it definitely helped up Barack's game to have such style by his side.

1. John F. Kennedy

John F Kennedy was the 35th President of the United States (1961-1963).

JFK was more than a Fashion Icon, he was a full fledged celebrity. But when it came to his style specifically, he had a couple of things going for him.  For starters, he was young.  The youngest president ever elected, and therefore more in touch with the latest trends and fashions, which are, let's be honest, a young mans game.  He was handsome, so when he threw on that skinny tie, those hip Ray-ban Wayfairers,  or some stylish wingtip shoes, it made him look more like a movie star than a president. And third, Jackie-O.  His wife was beautiful and elegant and an inspiration to women across the country.  “Behind every great man…”

 Happy election season.  May we all get through it in one piece.