Presidential Style: The Best Dressed Presidents In History

For the last few administrations, presidential style has been incredibly boring. The uniform of navy/charcoal suit, white shirt, and solid red/blue tie is strictly adhered to, and those who break the mold are met with harsh criticism (remember Obama’s tan suit?). If we look to the past, we can see that a few of the presidents were actually quite stylish. It might be a case of writer’s bias, but it’s no surprise that these presidents served during the first half of the 20th century. Here’s an overview of the style of three of the most jaunty presidents in US history.


Calvin Coolidge is not a president remembered for action. According to journalist Walter Lippmann, Coolidge was occupied constantly with “grim, determined, alert inactivity.” He earned the nickname “Silent Cal” during his tenure as Vice President and continued to live up to it when he ascended to the presidency in 1924. Amusingly, in 1927, Coolidge’s terse demeanor caused considerable political confusion when he announced his intention not to seek re-election.

Coolidge goes fishing presidential style

Coolidge goes fishing.

He called a press conference, and handed each reporter in attendance a card that simply read, “I do not choose to run for President in 1928”. The reporters struggled to determine the exact meaning of the words, and he refused any further explanation and left.

While his presidency is often overlooked, there is no denying that Coolidge had great style. Serving for most of the 1920s, President Coolidge exemplified the best of that era’s tailoring. In almost all of his photographs, he can be seen wearing the typical slim, high button suit, complete with narrow cuffed trousers. With a background as a New England lawyer, it makes sense for him to be impeccably dressed.

Although most official portraits and photos show him in formal morning dress, he still knew how to make the business suit look good. He was most often seen in plain worsted suits or business stripes, but was spotted wearing interesting summer outfits as well. As a true 1920s gent, he’s mainly seen in what are presumably starched, detachable collar shirts, and brocade ties. While this could seem a dandyish uniform to us, this was the norm back in the 1920s. He had a formal demeanor, both in an out of office, going as far as wearing a hat while shaving. The man even wore a fedora and a three-piece suit while fishing on vacation!

Honestly, Coolidge made this on this list for one specific outfit. In 1927, while vacationing in the Black Hills of South Dakota, he was given an outrageous cowboy outfit- a huge ten-gallon hat, red western shirt, and wide-legged chaps embroidered with “CAL”. Despite the laughter he received from reporters, he loved it and wore it proudly all summer.

The infamous cowboy outfit presidential style

Coolidge’s infamous cowboy outfit.

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Not only does Franklin Delano Roosevelt hold the distinction of being the only president to serve more than two terms, but he served during one of the most turbulent times in world history. He took office during the height of the Great Depression and passed away just before the end of World War II. The New Deal helped bring relief to millions of Americans and influenced American politics for decades. Fireside Chats helped keep morale and optimism up through economic hardship and war. He consistently ranks among the best presidents and was revered for years after his death.

FDR in a patch pocket stripe suit presidential style

FDR in a patch pocket stripe suit.

FDR might take the cake for me as the president with the best style. Unsurprisingly, he was born in the same East Coast upper-crust that graced the pages of Esquire in the 1930s.  Like Coolidge, he could be seen wearing the iconic slim, long silhouette of 1920s suits early in his career.  He apparently kept interest in fashion, as his suits evolved with the times.

Apart from some great suit combinations (which grew to be a bit more conservative during his tenure as president), one of my favorite images is of him in 1933, shaking hands with Vincent Astor.  He’s seen wearing what I believe is a play on the stroller suit: a patch pocket jacket with cream striped trousers; it’s even complete with a light-colored fedora and a pinned spearpoint.  In the 1930s, he sometimes wore unstructured suits with little shoulder padding. He wore one in 1935 during the signing of the Social Security Act. In contrast to the business suits around him, FDR made the bold decision to wear an unstructured light-colored summer suit.

Another great piece of his wardrobe is a wool cape, which he wore during the Yalta Conference.  It’s a quite ornate garment, complete with a velvet collar, satin lining, and a braided silk fastener. Apparently, the President preferred it over an overcoat, due to the greater freedom of movement it allowed. You can’t deny that he looked pretty regal wearing it over his suit. Maybe those Pitti guys were onto something!

FDR's famous cape and top hat presidential style

FDR’s famous cape and top hat.

I would be remiss if we didn’t mention Franklin Delano Roosevelt Jr., who seemed to pick up a few style cues from his father. He was a Harvard student throughout the 1930s, and was the epitome of early ivy style, with one famous picture showing him in a shearling collar overcoat, herringbone tweed jacket, and a pinned collar with a foulard tie. It’s practically something I would wear!

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On September 26, 1960, millions of Americans tuned in to the first-ever televised presidential debate. Richard Nixon was sick, tired, and thanks to his light-colored suit, blended in with the studio backdrop. John Kennedy, on the other hand, knew the power of appearances and came well-rested and well-prepared. As the famed (but slightly misleading) anecdote goes, those that saw the broadcast on television said that Kennedy easily won, while those that only heard it on the radio declared Nixon the winner of the debate. During the height of the Cold War, Kennedy successfully avoided nuclear exchange during the Cuban Missile Crisis and directed NASA to begin research that led to the Apollo 11 mission. Kennedy remains the youngest man to be elected president, and he and his wife became fashion and pop-culture icons.

JFK is often considered the most fashionable president, no doubt due to the love that 1960s fashion enjoys today.  It’s important to remember that he grew up during the late 1910s and he was fond of what I like to call “Golden Era” style.  There are pictures from his youth wearing traditional 1930’s attire, wearing cream flannels, navy jackets, and a pinned collar. One of my favorite images is him in a pleated patch pocket jacket, which is one of my personal grails.

JFK in the early 1930's presidential style

JFK in the early 1930’s.

Like the others on the list, his approach to style is influenced by his upbringing, again hailing from a wealthy east coast family.

JFK loved fastening all the buttons on his suit jackets presidential style

JFK liked fastening all the buttons on his suit jackets.

As university students became the arbiters of fashion, it makes sense that he developed a keen sense of style.

There’s even a great picture of him and FDR Jr. in the 1940s, where Kennedy is pattern matching with a pinstripe suit and a striped shirt. It’s quite fascinating to see how much fashion influenced him, as he truly kept up with what was in style. In the 1950’s, even Kennedy wasn’t immune to the bold look; one of his look at the time consisted of a heavily padded jacket with a swing tie.

The JFK we all know is the poster boy for 1960’s style.  His suits are generally very conservative two-button jackets with slim lapels and an equally slim tie. Some say that he wore paddock suits (since he fastened both buttons), but in my opinion, that’s false; paddock suits have a high button stance and if you compare his suits to others (sometimes in the same picture), his had a normal button stance. He probably just liked to fasten both buttons.

Casual style flourished in the 1960’s and was something largely absent from the wardrobe of previous presidents. Kennedy was spotted relaxing in sweaters, chinos, and loafers – a big change from the linen and tweed sport suits worn by his predecessors when OOO.  Additionally, we can all agree that his shades looked cool as hell. It’s no wonder why he is revered among the proponents of ivy style.


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Today, it seems that most male politicians opt for the same uniform – and nobody says they shouldn’t, considering their focus should be on more important things than style.

However, that’s exactly the appeal that the men on this list have for me; their attire did not only look effortless, but it spoke for them.  Looking at Coolidge’s starched collars, FDR’s cape, or JFK’s odd separates, we can catch a glimpse of their personalities. If clothes played a huge part in presenting oneself to the world in the past decades, today, in the Internet era, there are other ways for people in the public eye to express their personas.

Did social media kill our politicians’ style?

You can keep up with Ethan’s thrifting and vintage adventures on his Instagram (@ethanmwong) or on his blog Street x Sprezza.
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Ethan Wong
Ethan Wong lives right in the middle: he’s too modern for the vintage scene and yet too vintage for classic menswear. When not at work, he spends his time writing and taking pictures for his blog, Street x Sprezza, which is all about bringing vintage style into the modern day. With a large collection of thrifted vintage and contemporary clothing, he often wonders when his closet will finally implode.


  1. Bob Short

    February 21, 2018

    I vote for Martin Van Buren, the last President to wear ruffled shirts.

  2. Eric

    February 25, 2018

    I’m a fan of Harry Truman’s style. He was always well turned- out and had a fondness for double- breasted suits and spectator shoes. His wardrobe has been preserved and was quite extensive, unsurprising since he was a haberdasher early in his career.

    PS: JFK had his suits tailored in order to keep both buttons comfortably fastened because his war sounds required that he wear a back brace.

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