Lessons On Style From J.F.K.

Kennedy’s inauguration over 50 years ago signaled a new era in American politics as well as a return to presidential style that had not been seen in the White House since the days of Theodore Roosevelt. Whether boating in Hyannis Port or staring down the threat of Communism from the White House, a study of JFK’s style is a crash course in cool. Here are five sartorial tips to learn from arguably the best-dressed American President:

1. Wear the right jacket
Always a double-button, soft shouldered, and tailored to fit (see our Tailored Collection). JFK brought the blue blazer to the White House, as well as Harris Tweed sport coats and suit jackets that were either solid or with thin white pin stripes.

2. The versatility of the white dress shirt
Shirts were almost always white when dressed for the Oval Office. White goes well with nearly every imaginable pairing.

3. Keep the necktie simple
Neckties were either striped (the repp tie is an Ivy League staple) or simple geometric patterns. Leave the critters in the closet and go for something simple and classic.

4. The classic Wayfarer
Sunglasses were most often a pair of classic Wayfarers and JFK was among the ones to sport them the best. Wayfarers look great on nearly all face shapes and are a personal favorite. You may have noticed a pair of vintage Wayfarers in one of our previous lookbooks.

5. Ditch the hat
Notorious for not wearing hats, JFK is probably the reason why we aren’t walking around in fedoras today. There are some occasions when a hat can complete an outfit –like at a Lincoln convention, but for the most part, you can leave the hat at home.

Kennedy was a leader, not only of the free world but in how he helped define men’s fashion. As GQ wrote in 1961, “Cigar sales have soared (Jack smokes them). Hat sales have fallen (Jack does not wear them). Dark suits, well shined shoes, avoid button down shirts (Jack says they are out of style).” Now that is presidential leadership.


  • Just received my first order R740617084 following your appearance on Morning Joe. Love the shirts and was curious as to which shirt maker in London you apprenticed with? Having lived in London for 5 years I was a long time customer of Lewin andSons on Jermyn St.

    Look forward to a long term relationship with Ledbury. Thanks

    • Hey Charles,

      I’ll let Paul Trible know about your question. He apprenticed with Robert Emmett who is also located on Jermyn Street. We really appreciate your support.

      -Brian M.

  • I must make a small correction to #5: JFK was one of /many/ men who had mostly ditched their fedoras by the early ’60s. He was part of the trend (which had actually started in the ’30s as hat sales started a steady decline), not the starter of it. However, you’ll notice he wore a silk topper during his inauguration and there is the occasional photo of him wearing a period stingy brim fedora — one of the most famous being he and vice president LBJ at a baseball game. There’s a Snopes article about this, very informative.

    A lot can be said for a nice fedora though — keeps the sun out of your eyes and keeps your head warm in winter. Would look pretty stylish with a Ledbury shirt and sport coat. 🙂

Join the discussion

Your email address will not be published. Required fields are marked *