15 Most Iconic 1920s Fashion Looks You Can Recreate Fast

Mastering the Roaring Twenties – A Gentleman’s Guide to 1920s Style

Forget what you think you know about the 1920s. While the flappers were making waves with their scandalous hemlines, the gentlemen of the decade were quietly staging their own sartorial revolution.

This wasn’t just an era of extravagance; it was the dawn of the modern man’s wardrobe, a move away from the rigid formality of the Edwardian age toward a new, relaxed, and confident silhouette.

The ‘Roaring Twenties’ defined dapper for a new generation. From the halls of Ivy League universities to the smoky backrooms of speakeasies, men’s style became bolder, looser, and infinitely more expressive.

Whether you’re channelling the aspirational glamour of Jay Gatsby or the sharp edge of a Peaky Blinder, these are the essential looks that forged the decade’s timeless legacy.

1. The Three-Piece Suit – a 20s Cornerstone

The quintessential look for any man of standing in the 1920s was the three-piece suit. But this wasn’t the slim-fit uniform of today.

The 20s silhouette was about a comfortable, commanding presence.

• The Jacket
  Lapels grew wider, both in peak and notch styles, signalling a new confidence. The shoulders were natural, not heavily padded, and the jacket was often single-breasted with a higher button stance.
• The Waistcoat (Vest)
  A non-negotiable element, the waistcoat was the anchor of the ensemble, often cut high to create a clean, unbroken line from the high-waisted trousers.
• The Trousers
  Trousers were cut with a much higher rise and a straight, often generous, leg. A sharp pleat down the front was essential, and belt loops were just beginning to replace suspender buttons as the norm. Fabrics like heavy wool, flannel, and tweed in pinstripes, checks, and solid earth tones dominated.

2. Plus-Fours & Fair Isle Knits for a Sporting Look

For a day in the country or a round of golf, the uniform was the “Plus-Four.”

These baggy trousers extended four inches below the knee (hence the name), offering far more freedom of movement than the older, tighter knickers.

The look was perfected by the era’s biggest style icon, the Prince of Wales, who paired his Plus-Fours with high, patterned argyle socks, a crisp button-down shirt, and most importantly, a Fair Isle or V-neck tennis sweater.

This combination of textures and patterns defined the sophisticated, athletic style of the upper class.

3. Oxford & Brogue Shoes

Footwear became a key indicator of style. The classic leather Oxford was a staple for business and formal occasions. However, the decade saw the rise of more decorative styles.

The two-tone “Spectator” shoe (often in black-and-white or brown-and-white) became wildly popular, associated with jazz musicians, gangsters, and dapper men who weren’t afraid to make a statement.

Wingtip Oxfords, with their decorative perforations (broguing), were the perfect middle ground, suitable for both city suits and countryside tweeds.

4. Oxford Bags – The Collegiate Rebel

Born from a student protest at Oxford University—where knickerbockers were banned from lectures—Oxford Bags were the era’s boldest statement in casual wear.

These were wide-leg trousers, with some reaching an audacious 22 inches or more at the cuff.

Made from flannel and other lightweight fabrics, they were the epitome of Ivy League cool. Paired with a chunky knit sweater, a soft-collared shirt, and perhaps a tweed sport coat, this look screamed youthful rebellion and became a staple for the fashion-forward aristocrat and the aspiring student alike.

5. The Right Hat for a Finishing Touch

A gentleman would never be seen outdoors without a hat. It was the definitive punctuation mark on any outfit. While the working class favoured the soft, eight-panel “Newsboy” cap, the more refined man had options:

• The Fedora
  This became the dominant city hat, crafted from felt with its characteristic creased crown and flexible brim.
• The Homburg
  More formal than a Fedora, with a single sharp crease and a stiff, upturned brim. This was the hat of choice for businessmen and politicians.
• The Straw Boater
  In the summer months, the flat-topped, stiff straw boater was essential for picnics, sporting events, and leisurely strolls.

6. Power & Panache for a Gangster Edge

Popularised by figures like Al Capone, the “gangster” look was simply an exaggerated, more flamboyant version of mainstream fashion.

It was about projecting power – think bolder pinstripes on dark, double-breasted suits, contrasting two-tone shoes, a silk tie with a flashy pin, and a Fedora tilted at a confident angle. It wasn’t a different wardrobe, but a different attitude.

FAQs for the Modern Gentleman

Key Takeaways for Today’s Man

The 20s weren’t about dressing in costume; it was about the principles of timeless style. It taught us the power of a well-cut suit, the importance of quality accessories, and the confidence that comes from dressing with intention.

From the wide-leg trousers to the Fair Isle knit, the echoes of this revolutionary decade are still visible in menswear today. The Roaring Twenties proved that for a gentleman, style is eternal.