Bermudas for the Dog Days of Summer

How to survive the dog days of August without looking like a slob?

Jack Kennedy rolled up the sleeves of his cotton Oxford dress shirt and let it all hang out over his khaki walk shorts.

Bermuda shorts were the leisure summer garment of choice for the favored few in its salad days of the 1950s. After taking a Bermuda buggy ride with their best girl by their side, prep school and college scions of the establishment returned to campus for final exams from their rum-filled spring vacations loaded to the gills with the real thing purchased at Trimingham’s, the era’s top tier purveyor of the home product. J. Press got into the act in the early 1950s.

Best-selling author and cultural critic, Lisa Birnbach put her stamp on the genre in her 1980 classic The Official Preppy Handbook. The chapter titled Dressing The Part proclaimed, “Bermuda shorts are an integral part of a man’s wardrobe. They are worn cut like dress trousers, only hemmed just above the knee. Solid cotton or madras.”

Thirty-nine years later J. Press continues to fill the bill with a world-class cornucopia of Bermuda shorts available for end of season reductions. Pick of the pack — Seersucker, pink/white or blue/white; Patchwork Madras, pastel or dark shade; varieties of cotton Madras Plaids; Poplin, blue heather or light tan; stone-wash cotton chino, tan with lobsters or red with anchors.

The last word belongs to my friend, menswear historian and connoisseur G. Bruce Boyer in his latest treatise True Style daring to suggest, “Why not indeed wear a pastel chambray shirt, natty foulard bow tie, and lightweight blazer with a pair of Madras shorts?”

Bermudas go both ways.



At age 89 I still wear the blue and white check with white buttons sports coat that my Dad purchased the summer of 1974..The lapels are a little large , but it is still a smart looking jacket..

G. Richard Morris July 24, 2019

Mr. Press, could you tell us the difference in length between Bermuda and Jamaica shorts? I’ve yet to find a definitive answer and I think you’d be one of the few (along with Mr. Boyer) who could authoritatively weigh in on this.

Drew Poling July 23, 2019

At DePauw, amidst the cornfields of west-central Indiana in the early-’60s before the hippie sloppiness took over college campuses, it was still fashionable for girls and boys (for that is what we were then) to wear real bleeding cotton madras. Nothing looked so authentically casual in the Michaelmas term as late summer turned into Autumn in those bright college years!

Robert Emmaus July 22, 2019

The Bermuda short look lives on and still is one the enduring classics. That being said, the over-the-calf dress socks and loafers need to go.

Cheers from the Beta House in Lexington, Virginia.

Bill July 22, 2019

The last time I was in Bermuda, Trimingham’s existed. Unless I am mistaken, it may have bitten the dust. Meanwhile, standard business attire was Bermuda shorts complete with black knee socks as worn by the crew on your brochure, a necktie with a traditional collared shirt (many businessmen were wearing “OCBD”) and a summer weight jacket. It has been several years since my last junket. Nonetheless, the Bermudians may be a little less trendy and may have maintained a since if tradition?

Gerry Malmo July 22, 2019

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