When one first starts to become interested in the genre of vintage clothing, it is usually the evening wear that draws us in. The beautiful fabrics, embellishments, and styles, all evoking the glamorous atmosphere of bygone times. Yet, equally important was the casual wear. What did men’s vintage casual wear look like? What style of clothing was worn on a day-to-day basis? How do you go about dressing in casual or sporty vintage fashion?
Today, when we think of casual wear, we may think of T-shirts, jeans, hoodie sweatshirts, exercise pants, and sneakers. However, at the beginning of the 20th century, this was not the case. Casual wear as we now know it was developed from clothing designed for sporting activities – golfing, sailing, and horse riding, to name but a few. Before these new clothes for leisure hobbies became common, men dressed in 3 piece suits. With lighter fabrics, bigger prints, mismatched colors, and a looser fit, men’s suits became “casual.”
As we look back to the casual styles of the 1920s and 1930s, to us they may still seem really rather formal, especially when viewed through our modern 21st century eyes.
1920s Men’s Clothing
Popular men’s casual attire during the 1920s included plus fours – a baggy type of trouser that ended 4 inches below the knee (hence the term ‘plus four’). These were also available as plus twos, or plus sixes – the higher the number, the more the fabric would bag out over the hem.
These were worn when shooting or golfing, and crossed the divide from leisurewear to casual wear thanks in part to the Prince of Wales. He often wore plus fours while golfing, and was even known to wear extravagant plus twenties –‘HRH was dressed in plus twenties with vivid azure socks’ – In Their Fashion: The Windsor Style, Suzy Menkes.
The Duke’s impeccable style created a stir in the fashion world, catching the attention of Chanel – who then based some of her costumes for the ballet Le Train Bleu (which I have also mentioned previously in my Vintage Inspired Swimwear article) on his excellent fashion taste.
Plus fours are relatively difficult to get hold of in today’s times; the best place to look for an authentic style is traditional gentlemen’s outfitters or golf apparel – that may still be manufacturing them for the original purposes of sporting wear. Otherwise, smart tailored shorts paired with patterned knee high socks would be a worthy substitute for the late 30s to 1960s decades. Alternatively, if you know someone handy with a sewing machine, browse our men’s vintage pattern shopping pages for a number of plus four sewing patterns.
Pair plus fours or baggy wide legged trousers with a sports polo shirt, patterned socks, and a sportcoat. Add a straw boater or linen flat cap in the summer time, or in the cooler months add a layer of color with an argyle patterned or white pullover or cardigan sweater for a perfect 1920s casual style.
See more 1920s outfits:
- Learn how to create 10 different 1920s men’s outfit
- Men’s vintage workwear – overalls, work clothes, boots
- Banker, Barbershop singer/musician, or Bartender outfits
- 1920s casual men’s outfits– from suit to workwear, very trendy now
- Casual men’s vintage outfits from the 1920s to the 50s
- Swimwear – History of women’s and men’s swimsuits
- 1920s men’s costumes – Cheap Halloween, fancy dress or party costumes for gangsters, musicians, Gatsby, bootleggers, ect
1930s Men’s Clothing
The 1930s really did not differ all that greatly from the styles of the 1920s, if at all. As discussed in many a fashion history books, men’s fashion in general was slow-moving.
Striped or patterned blazers were popular during this time, especially during the warmer summer months. The striped blazer originated again from sportswear for cricket, sailing, or boating. Often, the color or positioning of the stripes on the blazer signified an allegiance to a particular sporting team. This was particularly evident in the early years of the 1900s, before they were adopted as purely casual clothing. The actual cut of the blazer itself originated from a naval uniform. We would again see uniforms infiltrating daily fashion choices after WWII, with the rise of the Bomber Jacket.
As recreated in the outfit above, a solid, striped or plaid blazer was often teamed with white ‘flannels’ – a casual trouser. Pair a patterned blazer with pale trousers and two-tone brogues for a perfect casual 1930s style. Add a straw boater or straw Panama hat for a great finishing touch in the summer months.
The look below is the late 1930s to 1940s very casual striped T-shirt, wide leg pants, belt, cap, and canvas boat shoes. Striped shirts gave a nod to nautical or sailor clothing popular in the summer time. The very casual sport cap was an acceptable alternative to straw hats. Ours here is a tan cotton cap, but a white or ivory linen would be cool as well.
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1940s Men’s Clothing
In the 1940s, casual wear started to become slightly more relaxed, and by extension, more comfortable. As part of the Make Do and Mend campaign, many garments were knitted during this decade, menswear included. Popular casual wear for men included sleeveless pullovers – sometimes plain, but usually with Fair Isle patterns in a mixture of shades. Men also wore V-neck sweaters over their shirts, with the shirt retaining that element of formality so the outfit did not appear too casual as to be deemed improper for those times.
Trousers became narrower during this decade, and due to austerity restrictions, certain design elements were prohibited. From 1942 on in wartime Britain, no turn-ups were allowed on trousers and the fly fastener could only be buttoned rather than zip fly. Gone were the wide bags of the late 1920s and 1930s — they were replaced by high waisted, modestly straight legged trousers instead.
Another similar look involves wearing a button down vest in a contrasting color and a patterned sport coat. This mix n’ match of shirt, vest, pant, and sport coat was very common in the 1930s and 1940s.
Leading up the even more casual 1950s, men removed the vest and simply wore a button down sport shirt. The difference between a dress shirt and sport shirt is in the collar. It was worn unbuttoned with a wide Byron collar resting over the collar bones. They were not worn with ties. They came in an assortment of rich colors: blue, green, maroon, yellow, and some patterns like plaid or windowpane. A modern version is a camp shirt (usually short sleeve) worn tucked in. The rest of the look is the same.
Casual pants were worn with a plain shirt and often had a pattern such a check, herringbone, or subtle plaid. Colors of casual pants were bolder than suit trousers. Blue, light blue, green, light gray, tan, ivory, and rich brown. The rest of the look is the same wide leg pants, two tone shoes, fedora hat, and belt. Simple, yet classically vintage.
One popular Halloween or vintage movie outfit is the Film Noir private eye/ detective or the criminal gangster. Wearing all black or grey clothing with a fedora hat and trench coat, the look is unmistakable. Learn more here.
See more 1940s men’s outfits
1950s Men’s Clothing
The 1950s witnessed a massive change to the casual wear market – and it was mostly down to the recognition of the teenager as a consumer. Teens felt that they didn’t want to dress like their parents, they wanted something different, something new. Previously, young adults were always dressed that way – precisely like miniature adults. There was very little deviation between childhood and adulthood, no ‘inbetween’ stage. But, with the 1950s came the birth of youth culture, and with it, a whole new genre of society.
Interestingly, we still see some parallels between the casual wear of the 1950s and the casual wear of the 1920s. Yes, the garments themselves may be worlds apart, but the initial uses of the garments remained the same – sportswear. The bowling shirt of the 1950s derives from the activity of bowling, the baseball jacket from the fields of baseball, etc.
It was during the 1950s that the t-shirt and jeans combination became increasingly popular – perhaps the closest our modern eyes can relate to casualwear style of today’s times. Popularized by James Dean and Marlon Brando, the jeans and t-shirt became acceptable daywear.
As a variety of styles were available to choose from during the 1950s, the scope of choice for casual wear is vast. Choose a simple t-shirt and jeans – styled to look of the era with a leather biker jacket and turn-ups on the jeans. Or, pair a bowling shirt with peg top trousers for a more preppy style. To add a splash of color, wear a Hawaiian shirt with casual 1950s trousers or shorts – if the weather is particularly sunny!
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1960s Men’s Clothing
The 1950s saw the division of styles and cultures almost like no other decade, and by the following decade we had Mods, Rockers, Teddy Boys, Beatniks and Hipsters – all these groups defined in part by musical interests or tastes in art.
By the 1960s, trousers started to become more closely fitting, tapering slightly at the hem. Pants were still worn on the waist, but as the decade progressed, they began to lower towards the hips. As the choice is so vast by this decade, perhaps choose a style that you can see yourself wearing with ease, then add some finishing touches to evoke the era. For a Teddy Boy style, opt for pastel shades in neatly fitting shapes, worn with smart shoes. For a beatnik, team a polo neck sweater with black tailored pants.
The 1960s was all about fit – tailoring at this time was immensely popular, with a revival in the Edwardian gentleman style.
Whilst some of the styles highlighted throughout this article may not fit in with our modern day definition of casual, they were indeed the casualwear items of their time. Whether you favor the striped blazers of the 1930s or the Fair Isle pullovers of the 1940s, there is sure to be a decade to match your style choices.
See 20 more 1960s men’s outfit ideas