This Friday marks 50 years since the untimely death of the 35th President John F. Kennedy, a man whose life and legacy continues to captivate the imagination on both sides of the pond. Half a century on he remains the best-dressed man to have occupied the White House, enduring as the definition of effortless American style and dignified elegance.

In tribute to the seemingly eternal style icon that is JFK, Street Gentry have prepared a five step guide towards Presidential cool.



Step 1: Ditch The Hat, Don Some Sunglassestumblr_lfp9ng5swk1qfv0zv.

  • Kennedy didn’t wear hats and soon after a nation followed suit. As American GQ said in 1961 “Cigar sales have soared (Jack smokes them). Hat sales have fallen (Jack doesn’t wear them).”
  • Accessories matter. Sunglasses are a key aspect of the iconic JFK image, whether combined with a suit at Presidential affairs or nonchalantly perched on top of his head on a yacht, Kennedy’s shades assured that he looked classy when dressing down and casual when suited up.
  • Get your own JFK wayfarers from Ray-Ban or get them fully customised from Lookmatic. And the great news is wayfarers suit all face types.



Step 2: Your Tailor Is Your Friend.tumblr_lkwl6kikTv1qzep2bo1_500

  • Although famous for his casual and natural style, Kennedy was actually meticulous about the fit of his clothes and inherited his love of English tailoring from his father.
  • With the price of simple adjustments and alterations relatively cheap and readily available, there really is no excuse for that suit sleeve to be warming your palm or your trousers legs to be bunching around your ankles. Kennedy had an ocean between his tailors, we’ve got them on our doorstep!
  • Kennedy’s suits and blazers were tailored to perfection, sitting a little closer to the body with the lapels in proportion to the size of the shirt collar and tie. This slim cut tailoring and attention to detail helped ensure that Kennedy appeared dignified, elegant and classy, as any self-respecting President should.


  • Kennedy is famous for ushering in a new era of two button suits, with a generation of Americans ditching the more formal three button suits for the more casual, sharper style preferred by Kennedy. It is less well known, however that Kennedy had his suit altered in such a way to accommodate his lifelong back complaints. Regardless of its origin the two button suit became a style staple across America in the early 60s and looks as fresh today as it did then.







Step 3: Embrace Tweed.The_kennedy_brothers._V233773449_

  • With Kennedy’s natural style instinct, switching between formal and informal attire was achieved with apparent ease, and the photo to the right is a perfect example of JFK personifying ‘smart-casual’. A key element of this relaxed look is the tweed jacket. Always soft shouldered and slim fitted, Kennedy brought the cool factor to the White House with a little help from Harris Tweed.
  • Raised in Massachusetts and educated at Harvard, Kennedy has become something of a poster boy for the Ivy League style that continues to have a strong influence on contemporary menswear. The tweed blazer is one of the cornerstones of this classic look. Worn with chinos, the tweed blazer, sports coat or suit jacket gives the impression of not having over-thought your outfit whilst still looking put together. Alternatively, pair your tweed with some dark denim for a more modern update. (Although this is straying from classic Kennedy cool.)
  • It’s often been said that Kennedy thought it was better to be slightly over-dressed than slightly under-dressed. To help make sure you don’t get caught out why not invest in some tweed. The Ludlow range from J-Crew offers a range of great quality sports jackets in a vareity of wools. Alternatively, if you’re after the real deal, Tk Maxx have recently began stocking Harris Tweed (Because although your style may be Presidential, your budget might not be!)


Step 4: The Sweater Never Fails.tumblr_lk0dsaZcyz1qj551io1_500

  • Another defining feature of the Ivy League look is the humble sweater. Whether Shetland, cable or Fair Isle the sweater is a comfortable yet casually sophisticated style staple. The photos of JFK loafing on sailboats and yachts with his family, wearing simple sweaters, penny loafers and trousers embody the carefree cool factor that is synonymous with Kennedy.
  • The sweater is a timeless piece that should form the foundation of every gent’s wardrobe. The key is in its simplicity and versatility.
  • We’re spolit for choice when it comes to crew neck sweaters, but J Press are famed for their range of Shaggy Dog sweaters. If you don’t mind compromising on material Uniqlo’s range of knitwear is both afforable and well made with cashmere and lambswool blends available. The cable knit also sits comfortably in the JFK style canon.


Step Five: If In Doubt, Go With The White Shirttumblr_mao3xlCg4n1qfjrwro1_500

  • While on duty the colour of Kennedy’s shirt invariably matched the colour of the Presidential residence. Timeless, sharp and elegant the crisp white shirt is a defining aspect of the Kennedy cool factor.
  • JFK built on the minimal foundation of the white shirt with simple and classic ties. Whether sporting Ivy League repp stripes or simple solids, the white shirt helped bring the colour and pattern of Kennedy’s ties to the fore.
  • The versatility of the white shirt makes it an essential staple for every mans wardrobe. White goes with pretty much everything so whether worn under a sweater, paired with some shorts and rolled up sleeves, or as the foundation of a suit, the white shirt is a go to item for any occasion.


    The Basic Ingredients of JFK Style: Two button suits, chinos, Ray-Ban wayfarers, shetland sweaters, navy and tweed blazers, simple ties, great tailoring, polo shirts, a confident and relaxed approach.



    “His unstudied sense of style is a constant touchstone when I design my men’s collections each season, he ushered in a whole new era of style— a convergence of Old World elegance and casual modernity.” Michael Kors




3 Responses

  1. Ian Moore

    I know that it has been said many times before in many different articles but JFKs’ sunglasses of choice were in fact American Optics Saratogas and not Wayfarers ( the slimmer arms are the give away ).

    • Quintessential Gent

      Hi Ian,

      Thanks for the comment and pointing that out. It prompted me to do a bit of further research and found this interesting post about the ‘wayfarer myth’. I think for the purposes of a general ‘guide’ to JFK style, however, Ray-Ban wayfarers still fit the bill.

      • Ian Moore

        I agree and for anybody wanting to emulate the style Wayfarers are a lot easier to obtain..( and a lot more affordable. There is currently a pair of tortoiseshell Saratogas on Ebay for £351.77 …(item: 121223452254 if anyone is interested )