Changes in fashion are often a reaction to changes in society, be it a war, a social movement or, in the case of the 1920s, the 18th Amendment which banned production and sales of alcohol. The country’s reaction to Prohibition was the exact opposite of what the law intended. More people than ever began drinking, only this time in illegal establishments called “speakeasies,” aptly named as a password often had to be whispered -- patrons had to "speak easy" -- to get in. With booze and live jazz flowing freely, women felt freer to shorten their hems and hair, while men wore sharp suits, fedoras and flashy ties perfect for being pulled around the dance floor.
The classic suit hasn’t changed much since it became a closet staple for men in the 1920s, and for good reason. A well-tailored suit in a neutral color evokes a timeless sophistication that men in the Prohibition era wore for almost every occasion. While today’s suits are made of lighter fabrics, suits of the '20s were made of heavy wool or tweed. Jackets could be single or double breasted, with high lapels and buttons that reached up to the center of the chest. In the early '20s, suit pants were cut fairly close to the body, but by the end of the decade, young men were wearing wide leg pants called “Oxford bags,” which could boast legs as wide as 16 inches. To really capture the feel of the roaring '20s, make sure your suit comes with a matching vest, and find coordinating suspenders to keep pants sitting high on the waist. To add personality to the neutral three-piece suit, men wore striped shirts in bright, bold colors with contrasting white collars.
To add a bit more color and polish to your soiree ensemble, tuck a triangle-folded silk pocket square into the front chest pocket of your suit jacket. If it’s chilly out, don leather gloves in a neutral dark brown, black or grey, or in a shade that matches your pocket square or tie. Bow and neckties were equally popular, as long as they were adorned with some kind of pattern, such as stripes, polka dots or checks. Embrace bold colors and choose a tie in an unforgettable hue to make a statement. Unlike today's belt-skimming ties, men in the '20s wore their ties a few inches above the waist of their pants.
Fortunately, the shoes that were in style in the '20s are still in style today, so you might very well have the shoes you need for your speakeasy soiree right in your closet. Defined by the decorative perforated holes, brogues in black or shades of brown would have been worn with suits, while fancier two-toned wingtips would have been worn with evening tuxedos
Hats and Hair
Above the shoulders a man in the '20s looked clean cut and dapper. Hair was kept longer on the top so it could be easily combed back, which you can achieve at home by slicking back your locks with a bit of pomade or styling cream. To complete the ultimate speakeasy look, crown yourself with a fedora, derby or bowler-style hat.