MOST STYLISH US PRESIDENTS

It was just election season in the United States, and being the fashion-conscious observer I am, the pure ridiculousness of it all was punctuated by the vanilla fashion sense portrayed on both sides of the aisle. While I wouldn’t say either candidate’s styles were particularly egregious (sans the orange man’s ill-fitting suits), it also didn’t seem like they cared whatsoever about how they looked beyond being broadly presentable. 

This is truly a shame considering we have had some quite dapper presidents in the White House through the years. So who were some of those stylish heads of state? Glad you asked. Let’s take a look at an unranked selection of such figures. 

Theodore Roosevelt

We start things off with a real throwback, because there tends to be a recency bias associated with the topic of presidential style. But Theodore Roosevelt flips that on its head. In a sea of boring contemporary politicians, Roosevelt set himself apart with an incredibly iconic look. A hearty mustache, pince-nez glasses and a burly stance made him an unmistakable figure. 

Teddy’s style was very clearly influenced by his time in the military, where his battlefield attire was more akin to the dress uniforms today’s soldiers wear. They were elegant with a purpose. This is reflected in the suits he wore while in office. They were fairly pedestrian with looser cuts–for mobility, I assume, and to project a more relaxed image. However, he wasn’t afraid to accessorize with pocket watches or matching ties and vests. 

But the real gems of Roosevelt’s style lie in what he would wear outside the office. An avid outdoorsman and conservationist, Teddy was famous for being a man’s man in this regard. Whenever he was out hunting big game he made sure to come correct with functional attire. Big hats and durable jackets were complemented by khaki or wool garments, and he capped it all off with a signature bandana tied around his neck. Today we are seeing a renaissance of techwear being brought to the street and outdoors people being seen as style inspiration. Over a century ago, a US president was living that life. 

Barack Obama

Speaking of recency bias, a particularly relevant figure in the topic of presidential style is Obama. Since he left office, his stature as a style icon has only increased, due in no small part to his successor’s failings in that regard. Even when he was president, Obama was thought of as someone who knew their style and really leaned into it. 

Obama brought a laid back and more modern business-casual style to the White House. What he wore was always clearly thought out, but it never looked like he was trying too hard. His suits weren’t overdone and obviously expensive, like the old guard, but also not ridiculously form-fitting as was the style in the early-2010s. They had sharp yet relaxed cuts, and were commonly in soft shades of darker colors. In this vein, I always thought of Obama as your friend’s cool dad who worked in finance but kept it real enough to send his kids to public school. 

A deliberacy in his style was also visible in his leisurewear. Whenever on an outing, Obama would throw off his blazer and tie then up the sleeves on his dress shirt. This aesthetic made him look right at home in a Gap campaign but not among the pages of GQ. He was a master at projecting an image–one through which he related to a broad spectrum of people.  Artificial or not, Obama’s style has quickly ascended the ranks in terms of presidential style. 

George H.W. Bush

This is another left-field selection many wouldn’t immediately gravitate towards, but there is no doubt the senior Bush had a great sense of style. When I try to approximate his style I would best describe it as a cross between a Wall Street yuppie and the generic grandfather from the wealthy side of the family in a 90’s comedy and I mean that in the best way possible. 

While he was of an older generation, he managed to appropriate contemporary motifs into his style. This would show through in a navy pinstriped suit with sturdy collars and subtle shoulder pads paired with large square glasses. Outfits like these give you a sense of the overall look he was known for throughout his time in office. 

That wealthy grandfather analogy from earlier also showed through in spades when he wasn’t in the White House. The fact is, Bush lived and breathed the Ivy League. He came from a family of substance who raised him in Connecticut and spent their summers in Maine. And of course, he is a legacy graduate of the prestigious Yale University. It is therefore no surprise that his leisure fits featured preppy staples such as boat shoes, white khakis, or light sweaters over polos. 

Harry S. Truman

Most people know Truman simply as the president that succeeded the legendary Franklin Roosevelt after his untimely passing during his unprecedented fourth term as president in 1945. What many know is the man had real style. Often we see politicians gravitate towards one suiting style, and they generally stick with it. But Truman somehow managed to pull off anything whether it was double-breasted, fitted, or had vests.

It wasn’t just suits he liked to have a wide variety of. Truman had a collection of over 90 pairs of shoes. Many of them were unsurprisingly oxfords and other dress shoes. However, it is clear from looking at his collection that he had a knack for flair when it came to materials and construction. It’s funny to see Truman’s shoe-collecting within the context of modern-day sneakerheads who get so caught up in a particular brand; failing to simply buy whatever they like. I dont think it’s a stretch to say that if Truman were around today that he would have a stacked closet consisting of a smorgasbord of different brands and styles. Mr. Truman, it seems, was living in a post-sneaker world over 70 years ago. 

John F. Kennedy

No serious discussion on presidential style would be complete or even worth having if it did not mention Kennedy. Despite this being an unranked list, I think most would agree he was easily the most dripped out president. Why might you ask? I think it lies in the fact that during his unfortunately short term he was a sex symbol.

His stature as a youthful and exciting figure in the political realm was translated into the things he wore and how he wore them. The suits he wore in office were always cut extremely well and tailored to his figure. They were also mostly in solid colors, which gave off major Mad Men vibes. Despite being the youngest president ever, the way he dressed and carried himself produced an air of confidence that told others he was fully capable of doing his job. 

Kennedy also personified Ivy League prep with a new edge. Where George H.W. Bush was Brooks Brothers, Kennedy was J. Crew. The underpinnings of traditional prep remained in his leisure fits. But he would always put something together that seemed to be taken straight off the shelf of a 5th Avenue department store. Most likely because it actually was. 

He would also add little pieces of flare to these outfits to really set them off. My personal favorites were Wayfarer-style sunglasses. Others would be a flight jacket or even a pair of socks. Kennedy simply oozed cool as a sitting president. In terms of style, he was more a contemporary to the leading men of Hollywood rather than the politicians on Capitol Hill. 

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