Men in an era without immediate threats, such as World War I or the pandemic, were free to buy nice outfits, and designer pieces by Claude Montana and Azzedine Alaia could afford lavish fashion choices that blended Hollywood retro with futurist styles.
Shirts for younger men typically featured detachable collars and single cuffs, though older ones preferred turndown-style shirts. Trousers were narrow at first but gradually widened by the end.
Jackets
Men’s formal wear underwent a dramatic evolution during the 1920s. Long tails were replaced with tuxedo jackets and heavy fabrics like wool were replaced by lighter materials like tweed and cotton for their suits; although still formal attire, these more lightweight fabrics allowed more casualty into men’s fashion. Furthermore, this decade saw the debut of patterned suits, which could be worn over white shirts with a tie or bow tie and finished with a newsboy cap for fun and casualness.
The 1920s witnessed the advent of vests and waistcoats as an accessory to suit jackets of either single or double-breasted style. Vests helped streamline silhouettes while matching materials like tweed or corduroy were often chosen to complete outfits. Men would usually also pair their attire with fitted polo shirts.
Leather coats were popular winter wear during the 20s. Usually available in black or brown hues, these jackets could be worn with trousers and suit jackets for a formal yet casual look. Sports jackets were another form of attire similar to suit jackets yet boasted less standard features like buttons and vents.
Workwear styles in the 1920s were more relaxed, featuring wide-leg pants and shirts made of lightweight cotton twill or linen and jackets with loose-fitting sleeves and soft shoulders for easy movement. Hats from bowlers to fedoras completed this look beautifully.
After years of pinched-in cuts and flat-fronted styles, softer and broader cuts were a refreshing change; they allowed flannels, tweeds, and corduroy fabrics to flow more freely across your head and look beautiful. Today these relaxed styles still look good whether going full Gatsby or casual Shelby.
Men’s jackets were handcrafted carefully during the Roaring Twenties, featuring narrow natural shoulders, wide lapels, and flap pockets. Single and double-breasted suits were available; earlier ones featured slim-fit construction, while those from later in the decade favored boxier silhouettes seen in gangster pictures. A matching waistcoat or vest often accompanied suits; when worn together, these were typically complemented with striped shirts and dark-colored loafers or oxfords for contrast; in summer months, a straw boater hat or top hat or homburg was essential;
Shirts
After decades of tight, form-hugging styles, the 1920s style marks a welcome return to roomier cuts that allow rich fabrics such as wool and flannels to drape properly without looking clingy. Plus, it gives off an impression that extra effort was put in when choosing menswear!
Dress shirts in this period were typically constructed of pastel or neutral hues with stripes in pastel neutral tones, often designed with rounded or pointed collars that could be worn with bow ties; others had pointed collars paired with shirt cuffs that often featured plain patterns but could feature pins, buttons or other decorations for additional flair.
As the decade wore on, menswear increasingly moved towards casual wear – driven in part by advances in textile production technology that yielded lighter clothing with greater variety and softer textures.
The 1920s also evolved from neutral hues and khaki suits towards bolder colors, such as suits with stripes or patterns; bold shirts such as pin-collars with more extended tips were popular, while Art Deco-inspired checks and paisleys first appeared. Club-collar shirts with contrast bodies became fashionable among other options; club-collar shirts with contrast bodies also gained momentum during this era, becoming more accessible. Finally, club collars with contrast bodies became part of everyday wear; pin-collars became common; club collar shirts with contrast bodies were popular; club collar shirts were popular as casual clothing options; club collar shirts featuring contrast bodies were popular as were pin-collars/spread collars/spread collars/spread collars/spread collars/spread collars/spread collars/spread collars/spread collars/spread collars with more extended tips (you can check out Tom Ford’s iterations of these). Finally, Art Deco-inspired checks/paisleys made their first appearance.
Formal occasions typically called for men to wear tuxedos and dinner jackets with bow ties in solid or striped styles; women often sported matching bow ties. Some tuxedos and dinner dresses included matching hats.
Country jackets were an adaptable piece for everyday wear. Usually, they featured earthy tones like brown or navy blue and earthy fabrics like tweed, with leather buttons, slanted pockets, rounded collars, and leather buttons. Country jackets could be worn with casual wear such as T-shirts and polo shirts or dressed up for special events with formal shirt and tie combinations.
Your way into an ideal 1920s look lies with selecting a double-breasted blazer from Anderson & Sheppard in a dark hue – ideal for creating that all-important insouciant slouch! Team this piece up with Kent & Curwen Peaky Blinders banded-collar chambray shirt, or opt for The Kooples’ striped shirt for a more casual approach to this period.
Trousers
In the 1920s, textile production techniques changed, opening up a wider variety of lightweight yet softer textile materials with lighter weights and textures than had been available before. As a result, men could now choose straight or wide-legged trousers that typically sat high up on their natural waist with deep seats secured with button-on suspenders; wider calf-length trousers were often paired with knitted sweaters.
Trousers were commonly made with gabardine fabric, a high-density warp-faced warp fabric that comes in multiple weaves and finishes – typically cotton twill with vertical ridges to give a sheen similar to suiting materials. Today gabardine comes in many colors to fit various needs for dress shirts, trousers, suits, and jackets.
Men who wanted to appear fashionable and fashionable during the twenties typically wore light-colored trousers paired with a suit, tuxedo, fedora trilby, or bowler hat for an elegant appearance.
Sportwear was also an innovative fashion development, often worn to social events like golf or bowling. Men would typically pair pleated or knickerbocker trousers with a sport shirt for the look, then complete their ensemble with loafers or sports shoes to complete it all.
In the 1920s, fashion became more sophisticated with the arrival of single-pleat trousers with side cinchers crafted from wool, cotton, and linen. Additionally, new types of footwear emerged; men often chose leather Oxford shoes featuring round or wider box tips to allow their feet to move more freely.
Hollywood greatly influenced men’s fashion in the Twenties. Stars such as Charlie Chaplin, Rudolph Valentino, and F. Scott Fitzgerald helped establish a stylish image associated with that decade. Recreate this look by wearing tailored suits in neutral colors such as gray or black combined with a white shirt, tie, and trilby hat – something Charlie Chaplin, Rudolph Valentino, or F. Scott Fitzgerald would do regularly during that era.
Shoes
As the 1920s heralded a new era of peace, prosperity, and freedom for men’s clothing to become less restrictive while formal wear continued to be popular, leisure clothing such as sweaters, plus-fours, and baggy trousers was more widely worn; workwear pants were introduced alongside workwear jumpers, caps, and caps as well as many accessories to express individuality were becoming common.
As part of these changes, men’s shoes also transformed. Gone were the bulky lace-up boots of yesteryear; instead, cap-toe Oxfords with laces up to the toe, shoe spats, wingtips, two-tone tennis shoes, and two-tone Oxfords became trendy – not to mention two-tone shoes and tennis shoes made of two types of material (typically leather or canvas for most designs; some shoemakers even began to incorporate reptile skin in structures), naturally coming in shades black brown or white for these shoemakers to design them in.
Gatsby-style dressing calls for two-tone shoes, opting for plaid as one of your tones for maximum effect. Or you could add some bebop flair by opting for tasseled loafers or two-tone Art Deco-inspired spectator Oxfords like Cheaney suede loafers from New & Lingwood (white-and-chestnut spectators are ideal), or Church and J Fitzpatrick Derby shoes to bolster dandyism a bit more.
The 20s was also an era when hats were popular and essential to any outfit. Fedoras, bowlers, and Derbys should be part of any man’s wardrobe, as they pair well with most ensembles.
These classic plaid spectator Oxfords make the perfect homage to their period while remaining practical for everyday wear. Wear them to work, school, or the pub! Pair them with tailored chinos, and you have yourself the perfect outfit. Furthermore, there is an assortment of colors so that you can find one that best complements you if needed – these plaid spectator Oxfords offer timeless yet modern style!
