If you think of men’s 50s outfit ideas, your mind may immediately conjure up images of rebellious young men in leather biker jackets with greased up pompadour hairstyles. A time where everybody looked like The Fonz, Danny from Grease, or James Dean. Well, this wasn’t quite the case.
The “Fonz” in Happy Days
While this ’50s Greaser costume was worn towards the end of the decade, the 1950s was largely about the wholesome all-American look.
Although the Cold War and threat of nuclear weapons loomed over the heads of Americans during the fifties, it was a decade when the country could finally breathe a collective sigh of relief. This was a time after the tumultuous events of the ’30s and ’40s, when money and jobs were in short supply and men were sent to war.
America during the 1950s was booming. People had more leisure time than ever before, and life was pretty darn good.
1950s Men’s Outfit: Conformity
Oscar’s vintage 1950s grey striped sack suit
Following the short-lived Bold Look of the late forties, conformity was the order of the day in post-war America at the start of the fifties.
Men that returned from military service were keen to look like good clean-cut Americans to fit in with the ‘establishment.’ Dark office suits in blue, brown, and charcoal were the popular choices and of course, you weren’t properly dressed in the 1950s unless you were wearing a fedora hat.
Business attire has always been quite subdued in color, but even neckties, the item where men could usually have a little fun, were quite dark and plain in style.
A sea of grey suits and fedora hats in the 1950s movie The Man in the Gray Flannel Suit
This identical way of dressing was almost as if men had swapped one uniform for another. This perceived stodginess and sameness was perfectly captured in the 1955 book The Man in the Gray Flannel Suit, which was made into a movie (watch it on YouTube) the following year with Gregory Peck as the young World War II veteran.
Gregory Peck – The Man in the Gray Flannel Suit (1956)
The sack-style suit became the standard for American business attire and was also adopted by those with an Ivy League persuasion. A loose cut, the sack suit usually consisted of a single-breasted three-buttoned jacket with natural shoulders (no padding) and no trouser pleats.
Sack suits are still commonly available (look for classic or traditional cut, not skinny or modern.) Wear a grey suit with a white shirt, dark knitted tie, and black Oxford shoes for a 1950s business outfit.
1950s Conservative Menswear
1950s Men’s Casual Outfits: Vacation
Loud and Proud: The 50s Hawaiian Shirt
1951 Whitmont Hawaiian Shirts
Following the horrors of war, the hard-working American man could now sit back and enjoy more time with his family.
In sharp contrast to dark business suits, 1950s men’s fashion was more colorful when men were away from work.
During warmer months, Hawaiian shirts enjoyed enormous popularity. The Hawaiian shirt dates all the way back to the 1920s, when it became worn by holidaying film stars. Indeed, it even became weekend wear for Presidents Eisenhower and Truman.
The shirt gained a wider appeal in men’s fashion following the end of World War II and in the decades that followed. Heck, even Frank Sinatra and Montgomery Clift wore them in 1953 movie From Here to Eternity (play at 18:55).
From Here to Eternity, men in Hawaiian shirts
Vintage Hawaiian shirts can be found relatively easily, and there are many reproductions too if you’re looking for 1950s menswear clothing ideas. Find one you like and bask in its garishness!
A Hawaiian shirt is perfectly paired with a pair of high-waisted pleated pants and saddle shoes. The pants were often a variant on the dress pants worn for business, made of loose wool flannel.
1950s Men’s Casual Summer Fashion with a Hawaiian Shirt
Casual: Men’s Bowling Shirts
Brother to the Hawaiian shirt is the iconic 50s bowling shirt. Men’s 1950s bowling shirt had colorblock panels of the “team color” and the team name embroidered on the back. For actual bowling thee shirt was worn untucked over pleated pants, dress sock and bowling shoes.
1965 mens bowling shirt
Today’s the 50s bowling shirt name also applies to Camp Caller shirts with atomic art symbols, geometrics, and novelty prints (guitar, piano, car, flamingo, pinups, Route 66 etc) These 1950s casual camp shirts were more of an early 60s thing but… close enough.
50s bowling shirt outfit
Oscar wears camp shirts all summer. His favorite brands are Steady and Lucky Paradise but you can find cheaper bowling shirts and camp shirts online. Pair them with slacks, chinos or blue jeans and even shorts in the summer. You can wear them tucked in with a skinny belt or untucked.
Camp shirt with atomic art, slacks, fedora hat and sunglasses
1950s Casual- Everyday Comfort
Vintage daywear for men, especially the 1950s styles, has been steadily growing over the past few years. Even more so for the 1960s. Bowling shirts and Hawaiian shirts have always been around, but classic ’50s menswear is a little more dressy, yet still casual and comfortable for everyday use.
Oscar here has been gradually collecting vintage 1950s clothing as well as good reproduction clothing for his daily wardrobe. His essentials are: A wide brim vintage hat (fedora) in brown, blue, grey, and straw; camp collar shirts, pullover knit shirts/polo shirts; a light gab jacket or bomber jacket; high waisted pants and dark denim blue jeans; a skinny belt; a vintage sweater and long overcoat; and vintage shoes (two-tone, wingtips, saddles, loafers, boat shoes). He also wears horn-rim glasses.
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- Swanky’s Vintage Jacket and Pants. Vintage Shirt and Shoes. New Fedora Hat.
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- Genuine Vintage from Head to Toe
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- Casual polo shirt and Gab jacket
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- Bowling shirt and jeans by Relco
One popular style of shirt that came back in fashion recently is the retro knitted shirt. In the 1950s these were knitted tee shirts with cartoon/artsy designs for kids and adults or plain or striped. They came in pullover t-shirts, collared polo shirts and button down cardigan style shirts with vertical and horizontal stripes, chain links, and geometric patterns.
1957 Tommy Sands wears a knit shirt
The movie The Talented Mrs. Ripley dressed Jude Law in many knit shirts for a Riviera look.
The Talented Mr Ripley movie still
Shop retro knitted shirts from these brands. For a 50s look pair them with pleated slacks, skinny belt, and casual shoes such as suede loafers or oxfords.
1950s knit shirt by Collectif at Unique Vintage
1950s Men’s
Preppy: College Kids
The 1950s marked the dawn of the adolescent. Granted, teenagers existed before this time, but the pre-1950s teenager was markedly different from the teenager that we know and love now.
1950 Students at Princeton
In the decades before the fifties, teenagers wore clothes similar in style to adults and in truth, this was still the case in the early part of the decade. The Ivy League ‘preppy’ outfit favored by college students was still relatively conservative, although less formal and relaxed.
Students were seen in suits, or certainly at least sports jackets and smart pants. Clashing patterns were exceptionally “cool”
1954 Preppy look for Obert Wagner
If a tailored jacket wasn’t worn, then it would be replaced with a cardigan sweater for a slightly more casual impression. Layering a sweater vest in bright color or pattern (argyle, fairisle, diamonds, tennis stripes) was critical to the preppy look.
As a sign that youth culture was beginning its ascendance, young men adopted All Star basketball shoes on their feet and ties were removed in favor of an open neck collar (buttoned up without tie was also popular in 1950s men’s fashion). Athletic types would also be seen both on and off campus in letterman jackets and cardigan sweaters, perfect if you like the casual sporty style.
1950s letter cardigan sweater
If you’re searching for 1950s menswear clothing ideas, going for a preppy Ivy League look is really simple to recreate. There are lots of 1950s style men’s clothing for sale today, including sweaters and pullover vests, letterman jackets, button-down shirts, loafer shoes, and chunky glasses.
1950s Ivy League “Preppy” and “Sporty” Looks
A similar costume is for a 50s socks hop men’s outfit. Here I paired a letterman cardigan sweater over a white dress shirt with pleated pants and saddle shoes.
Men’s sock hop or preppy outfit
Wild Ones, Greasers, and Rebels without a Cause
Few young men wanted to be seen as a ‘bad’ boy in the typical greaser fashion of leather jacket, white t-shirt and jeans. The ubiquitous t-shirt was actually considered to be underwear in the fifties, which is one of the reasons why the Marlon Brando and James Dean outfits were so shocking.
Marlon Brando ~ The Wild One(1953)
Although it’s quite common today to see people at the store wearing pajamas, it would still be relatively surprising if somebody was seen buying groceries in their underwear.
While Marlon Brando’s iconic movie The Wild One caused leather biker jacket sales to soar, James Dean’s Rebel Without a Cause had the same impact for t-shirts. A plain white t-shirt, revealing those manly biceps, combined with dark blue dungaree jeans is such a classic outfit choice for the young man about town.
1955 James Dean wears a Harrington jacket in Rebel Without a Cause
Along with Elvis, who wore one in the 1954 movie King Creole, James Dean is also credited with helping to make the Harrington windcheater jacket ( or Golf Jacket) a classic menswear staple.
A lighter alternative to leather, it provides ideal protection from the wind and rain. Since then, it’s been worn by all manner of people including Steve McQueen and Daniel Craig. Such is its legendary appeal that even I have one. After all, we all want to exude a little James Dean cool, don’t we?
1950s Rebel / Greaser Style- Levi’s vintage jeans and t-shirt, moto jacket and engineer boots.
See more Greaser outfit ideas in this article: 1950s Greasers: Everything You Know about Greasers is Wrong
1950s Men’s Workwear
The Greaser’s outfit was heavily inspired by men’s denim workwear. A 50s denim on denim outfit is classic wardrobe for Rockabilly and classic car collectors.
Teens in denim
50s workwear by Red Tornado
Denim wasn’t the only 1950s workwear clothing, nor the most common. Coordinated work shirts, trousers and jackets with a necktie and cap had men looking professional, even on the dirties jobs. See more 1950s men’s workwear clothing.
Men’s 1950s Western Wear
Influenced by the hugely popular westerns on television and at the movie theater, the cowboy style was a well-liked casual look adopted by men. It’s no wonder, really, as surely every man dreams of being a cowboy.
Men’s Button Down Shirts
Cowboy shirts are a great outfit, but if you don’t have one, then a plaid shirt is a great alternative as well as being super popular and sold in most menswear retailers. For true westernwear style, tie a bandanna around your neck and dig out a pair of trusty dungaree jeans for a rugged workwear 1950s outfit. With these men’s clothing ideas, before long, you’ll be walking like John Wayne and herding cattle like a pro. Now, where did I put my horse?
1950s Western Wear Outfit
Many many years ago Oscar pulled this look off:
Plaid Western Shirt, Dark Blue Jeans with a Roll Cuff, and Black Boots
1950s Men’s Formal: Prom King
Are you taking your date to the 1950s prom? You will need a 1950s tuxedo because young guys dressed up for such a special occasion. Most prom kings wore a white shawl collar tuxedo jacket over black tuxedo pants and white tuxedo shirt with black bow tie. A pink carnation or any color to match your date’s dress was the finishing touch.
1950s prom in black and white formal wear
1950s tuxedo outfit
White jackets were not the only formal trend in the 1950s. Sport coats and tuxedo jackets were also cream, beige, light grey, light blue, dark blue, red and black (lapels matched jacket.) Adding a narrow bow tie made the look more formal but a skinny tie was also acceptable.
1958 men’s sport coats- mix and match trousers and jackets
Some famous teen idols wore brightly colored tuxedo jackets- a trend that would influence 1960s men’s formalwear. Bright blue, teal, red yellow, pink and big patterns like plaid were all fair game. They even stared wearing cummerbunds and vests again. Notice these are back on trend now?
Learn more about men’s 1950s formalwear.
Late 50s plaid jackets, vests and cummerbunds
1950s Film Noir – Private Investigator
The era of Film Noir in the 1940s and 1950s is a costume popular theme for parties this year. Dressing like the PI or detective such as Humphrey Bogart or Gary Cagney usually means wearing all black and grey. For a color version of this outfit, wear a tan trench coat and brightly colored tie. Learn more about this outfit here.
Men’s 1940s-1950s PI, detective or undercover cop FilmNoir outfit / costume idea.
These are just a few 1950s menswear styles you can easily re-create. Need more? How about these:
- Halloween costumes – Milk Man, Retro Bowler, Nerd, Grease T-Bird, Teen Idol, Elvis, Diner Waiter, Teddy Boy, baseball player, Ricky Ricardo.
- 1940s Men’s Outfits – Many of these casual looks would have been worn in the early 1950s.
- Accurate Men’s 1950s Car Show Outfits- How to dress for a 1950s car show as an owner or spectator
- Sailing Clothes – For Summer, the boating or sailing man’s outfit.
- 1950s Men’s Summer Outfit Ideas – Casual, easy hot weather friendly 50s men’s outfits
- Vintage Men’s outfits – Tips on wearing a vintage style every day here and for fall/winter here.
- Men’s Vintage Clothing Stores – Reproduction, inspired, vintage, and handmade sources. A BIG list
- More 1950s men’s outfit ideas and photos
Debbie Sessions has been teaching fashion history and helping people dress for vintage themed events since 2009. She has turned a hobby into VintageDancer.com with hundreds of well researched articles and hand picked links to vintage inspired clothing online. She aims to make dressing accurately (or not) an affordable option for all. Oh, and she dances too.
