Bermuda shorts originated with the British Army for wear in tropical and desert climates, and they are still worn by the Royal Navy. During the Second World War there was a shortage of clothing in Bermuda. According to Jack Lightbourn, former Executive Vice President of the Bank of Bermuda, the general managers of the two banks in Bermuda, The Bank of Bermuda Ltd and The Bank of N.T. Butterfield and Sons Ltd were concerned that their male employees would not have suitable clothing to wear.
They arranged for a local tailor to make two pairs of shorts, modeled on the shorts of the British military, for each of their male employees. The shorts were made from a very itchy grey flannel material, and each employee was supplied with two pairs of heavy grey wool long socks to wear with the shorts. This was the beginning of Bermuda shorts as business attire in Bermuda. In the post war period local merchants such as Trimingham Bros. and H.A. & E. Smiths improved the design of the shorts and used bright colored materials as the shorts became more popular.