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Thomas Pink's style kings of the White House

With the attention of allies, enemies and citizens of the world on them, America’s presidents have to consider what messages they convey through all modes of communication – including the clothing they wear. Here, we home in on this fascinating slice of the sartorial world, and rank our top five presidents according to their sense of style.

Barack Hussein Obama II (20 January 2009 – 20 January 2017)

While Barack Obama was revolutionary in being America’s first Black president, he was known for wearing only a select couple of suits during his time in office, as he wanted to minimise all other forms of decision-making while focused on his presidential duties. Very Steve Jobs. According to former First Lady Michelle Obama, he wore the same black tuxedo to formal events throughout his eight years in the White House. So you’d be forgiven for assuming his wardrobe was far less stylish than his rhetoric. Yet, the suits that were his staples were characterised by slim cuts that embodied elegant, contemporary masculinity. Obama’s presidential tailor, Martin Greenfield, revealed that Obama loved the softest Italian fabrics. The Nobel Peace Prize-winning president also made countless appearances with rolled-up shirt sleeves, which gave him a hard-working aesthetic. That photos of this iconic look date back to his time at Harvard Law School suggests, however, that it was not expedient political messaging, but an intuitive part of his style. Elsewhere, he appealed to ordinary Americans by rocking simple combos of jeans with tucked-in shirts. What Obama personifies is the importance of finding flattering garments you can pull off – and put back on – time and again.

Navy Blue Knitted Merino Wool Zipped Bomber

Tailored Fit Formal Plain Poplin Shirt

Black Tailored Fit Pure Wool Evening Jacket

Harry S Truman (12 April 1945 – 20 January 1953)

In many cases, a president’s fashion sense can be attributed to the expert advice of his tailors, with a little extra help from the First Lady. But the sartorial awareness demonstrated by Harry S Truman throughout his time in office was no matter of chance. A quarter of a century before his first presidential term began, he ran Truman & Jacobson haberdashery in Kansas City, Missouri, with Eddie Jacobson, a friend who he had served in the US Army with during World War I. Hence, his brazen penchant for bold shirts and statement bow ties featuring geometric patterns or colours that contrasted with his suits, and the fluency with which he wore a great variety of garments, among them single-breasted and double-breasted suit jackets in almost equal measure, as recently portrayed by Gary Oldman in the blockbuster Oppenheimer.

Brown & Blue Diamond Biscuit Motif Silk Tie

Burgundy Red Silk Satin Bow Tie

Black & White Tailored Fit POW Check Wool Jacket

Ronald Wilson Reagan (20 January 1981 – 20 January 1989)

Famous not only for charming audiences with well-delivered jokes, but for being the first Hollywood actor to become US President, Ronald Reagan clearly had an astute awareness of his own appearance and how he came across. Certain scholars of international relations even speculate that his famous 1983 television broadcast on the Strategic Defense Initiative might have been a brilliant bluff designed to pressure the Soviets into worsening their already strained economy. In any case, if anyone had the guts to depart from the conventions of presidential dressing, it was Reagan. Unlike his forebears, he donned suits in a great variety of colours, most notably his solid or striped and brown ones, which had fans throughout the country soon purchasing their own. While he used a plain white shirt as a versatile foundation for most of his suits, he consistently wore visible French cuffs fastened by complementary cufflinks. The suits themselves tended to comprise pleated trousers and single-breasted jackets adorned with white pocket squares. Beverly Hills-based tailor Frank Mariani made several of Reagan’s bespoke suits from luxurious materials, such as super 100s wool and cashmere fabrics, which lend themselves to a polished look. According to Mariani, the president’s favourite suiting colours were different shades of blue and brown, and he had a particular taste for plaid too. In terms of silhouette, his preferences revolved around relaxed, boxier cuts with accentuated shoulders.

White Tailored Fit Formal Cotton Basketweave Shirt

Navy Blue & Yellow Regatta Stripe Silk Woven Tie

Navy Blue Classic Fit Merino Wool Unstructured Jacket

Theodore Roosevelt Jr (14 September 1901 – 4 March 1909)

Although there are many images of Theodore Roosevelt wearing outdoorsy clothing before his presidency, the bespectacled, moustachioed Mount Rushmore legend was a loyalist of Brooks Brothers, who have been the common denominator of a whopping 39 US presidents’ wardrobes. The company contributed to many of Roosevelt’s refined three-piece suits, which he combined with an extensive variety of hats and his famous monocle. The look this created might appear to modern eyes like something of a caricature of a bygone age, but in Roosevelt’s time it conveyed a quintessential American gentleman, albeit one with more than a dash of the dandy in him. His iconic monocle – a reminder of his eyes having been damaged in a boxing match – spoke of his masculinity, but also of his being an intelligent man of letters, a kind of early Hemingway. He displayed a great fondness for embellishing his outfits with accessories and often did so not only through the aforementioned hats but gold chains and bold ties too. Just as Reagan would later elevate brown suits to the sartorial stratosphere, Roosevelt was also a fashion trailblazer. It was during his administration that America became involved in the construction of the Panama Canal and in 1906 he appeared in many photographs at the site sporting a flamboyant light suit and matching Panama hat. This not only publicised the construction effort, but also popularised the hat – along with it the misconception that it came from the eponymous country rather than from Ecuador.

John Fitzgerald Kennedy (20 January 1961 – 22 November 1963)

When considering the best-dressed presidents, it would be almost impossible not to mention JFK, since he springs to mind for epitomising the preppy Ivy League style of the 1960s, one of the most influential moments in American menswear. His predilection for well-made clothing was evident during the 1959 campaign trail, when he sported custom- made garments, such as his Shetland-tweed herringbone topcoat made by Savile Row tailor H Harris, which had a branch in New York. Interestingly, a navy suit of his might have changed the course of US politics, since it made him stand out in the first-ever presidential debate to be broadcast on television. This was shot in black and white, and his opponent Richard Nixon blended into the background, having made the mistake of putting on a grey suit that day. Soon into his presidency, Kennedy made the switch from H Harris to Chipp, the favourite clothing company of his brother Bobby. Chipp was in large part responsible for JFK’s preppy wardrobe. The suits it made him had suppressed waists that accentuated a masculine torso and were constructed to accommodate the brace he wore to assuage his chronic back pain. The president often opted for slim suits and slimmer ties. When it came to the former, he stuck to classic colours typical of statesmen taking care to dress seriously, but made these more interesting with subtle pinstripe patterns. When he ventured outside the Oval Office, he experimented with looks that included chinos, Oxford cotton shirts, crew-neck jumpers and penny loafers, which made him look as if he might have appeared alongside Dustin Hoffman in The Graduate. Indeed, he was perhaps the most adept president at combining garments, whether it was a wool-knit cardigan with white pleated trousers or a formal jacket with chinos. The nautical styles he adopted satisfying his passion for sailing are classic James Bond, while his iconic tortoiseshell sunglasses displayed an excellent sense of taste.