
To me, the roaring 20s are best characterised by Cyd Charisse and Fred Astaire swing dancing to jazz.
For many, myself included, the 1920s will be best characterised by Prohibition and the 3 piece suits favoured by both G-men (FBI agents) and gangsters ala Al Capone himself. What started from a little noticed trend of fedora wearing celebrities like Timberlake and Johnny Depp has reached full circle two tone brogue shoe proportions driven in part due to HBO’s new hit series Boardwalk Empire starring Monsieur Steve Buscemi. Here are some men’s style tips to get you started in fine “gangsta” style:

For Boardwalk Empire, John Dunn and Lisa Padovani used as much real clothing as they could. They rented houses in California to house all the clothing for the period even.
1920s Style Rules that exist today (or are making a comeback)
- Men’s suits started to be fitted to the waist
- Unpadded, single or double-breasted styles were equally acceptable
- 3 button suits went as high as the chest. They buttoned the top button.
- It saw the birth of the trouser crease down the front. It made a man look refined and striking.
- They loved the knitted wear.
- Shoes were brogue in two tones for daily wear. Patent leather for dinner functions.
- Hats, ties and bow-ties were essential
- Birth of the permanent handkerchief in jacket pocket.
- Fabric choices of the day: Moving away from wool, designers used Tweed and flannel
- Colour palettes of the day: blues, browns, greens including beige, cream and tan.
You can read about that era over at Augustman.com or follow this handy visual guide:
- Michael Pitt as Jimmy Darmody. The dawn of the automotive age heralded new sartorial necessities like the driving cap.
- Primary colours like blue made a statement and were popular choices in the 1920s, as were the persistant hat (bowler, fedora, etc) and tie (both neck and bow configurations).
- For Boardwalk Empire, John Dunn and Lisa Padovani used as much real clothing as they could. They rented houses in California to house all the clothing for the period even.
- Vincent Piazza as Lucky Luciano. Tie pins were de rigeur of the day and if you notice the suit jacket button placement, the top button on a three button suit is chest level.
- With Steve Buscemi on the podium, we get a better look of how high the suits were buttoned. The 20s were also an era of “meaning business”
- Men and men’s styles were rapidly moving away from the Edwardian era but it was still gentlemanly to appear dressed in formal wear for dinner functions as a sign of marked respect.
- Tweeds and checks were in, as were flannel. Men of the era either went with pocket square or flower in lapel combinations.
- The tie pin held neck tie firmly in place. It was gentlemanly not to appear dishevelled or “out of order” in anyway. Dress codes were relaxing but not to the point of open collared looks.
- Men’s fashion moved quickly away from wool but wool was still a fashionable choice and an essential staple in many wardrobes still- Michael Pitt as Jimmy Darmody before his rise as a gangster.
- Jimmy is in the company of Al Capone (pictured centre). As you can see, his sense of dressing has changed, much like many men of the era, moving from harsher Edwardian looks to a gentler but better refined 1920s sensibility- the 3 piece suit for any time of day.
- Gents of the era were never without their hat. It was polite to tip or dob your hat to ladies.
- Slicked back hair was not uncommon either.
- If you want to look at a man’s fashion evolution, look no further to Michael Pitt’s character on the show. Jimmy went from being Nucky’s driver till successful gangster and it all began with Capone’s tailor hook up.
- Michael Kenneth Williams as Chalky White. Notice his two tone brown shoes in brogue? White separated collar on red shirt? Subtle, subliminal, sublime.
- Pink pocket square piece de resistance. Striking and perfect compliment to a well cut check suit.
- To me, the roaring 20s are best characterised by Cyd Charisse and Fred Astaire swing dancing to jazz.
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