How to Dress Like the 50s with Jeans for Guys: Master the Classic Style for Men in 2023

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how to dress like the 50s with jeans for guys

Popular Fashion Trends for Men in the 1950s

The 1950s was a time of classic and polished fashion for men. The popular fashion trends of this era were heavily influenced by Hollywood stars and American icons such as James Dean and Marlon Brando. Tailored suits were a staple in men’s fashion, with slim-fitting jackets and high-waisted trousers being the norm. Men also embraced casual wear, with button-down shirts, sweaters, and jeans becoming popular choices for everyday attire.

Hair styling was also an important aspect of men’s fashion in the 1950s. Pompadours and slicked-back hairstyles were common, often achieved with the use of pomade or hair gel. Accessories such as fedora hats, suspenders, and pocket squares added a touch of sophistication to outfits.

Key Fashion Trends:

  • Tailored suits with slim-fitting jackets and high-waisted trousers
  • Button-down shirts and sweaters for casual wear
  • Pompadour and slicked-back hairstyles
  • Fedoras, suspenders, and pocket squares as accessories

Influential Figures:

Icons like James Dean and Marlon Brando set the tone for men’s fashion in the 1950s. Their rebellious yet stylish looks inspired many individuals to adopt similar styles. Other influential figures include Frank Sinatra with his tailored suits and Elvis Presley with his unique blend of rock ‘n’ roll style.

Popular Brands:

Brands like Levi’s, Wrangler, and Lee became popular choices for jeans during this time period. For tailored suits, brands like Brooks Brothers and Hart Schaffner Marx were highly regarded for their quality and craftsmanship.

Overall Aesthetic:

The overall aesthetic of men’s fashion in the 1950s was polished, sophisticated, and effortlessly cool. The emphasis on tailored clothing and attention to detail created a timeless look that is still admired today.

Incorporating Jeans into a 1950s-Inspired Outfit for Men

Jeans were not commonly worn by men in the 1950s, as they were primarily seen as workwear or casual attire. However, if you want to incorporate jeans into a 1950s-inspired outfit, there are a few key elements to consider. Firstly, opt for high-waisted jeans with a straight or slightly tapered leg. This style was popular during the era and will help create an authentic look. Pair your jeans with a tucked-in button-down shirt and a leather belt with a simple buckle. To complete the outfit, add a bomber jacket or a cardigan for layering.

Choosing the Right Fit:

When selecting jeans for your 1950s-inspired outfit, it’s important to choose the right fit. Look for jeans that sit at your natural waistline and have a straight or slightly tapered leg. Avoid skinny or bootcut styles, as these were not common during the 1950s.

Accessorizing Your Jeans:

To enhance your 1950s-inspired outfit with jeans, consider adding some accessories. A classic fedora hat can instantly elevate your look and give it that vintage touch. Additionally, don’t forget about the importance of footwear – opt for leather loafers or brogues to complete your ensemble.

Common Styles of Jeans Worn by Men in the 1950s

The most common styles of jeans worn by men in the 1950s were straight-leg and high-waisted designs. These styles emphasized a clean and tailored look while providing comfort and durability.

Straight-Leg Jeans:

Straight-leg jeans were popular among men in the 1950s. They featured a straight cut from the hip down to the ankle, creating a sleek and streamlined silhouette. These jeans were often made of sturdy denim fabric and had minimal embellishments or distressing.

High-Waisted Jeans:

High-waisted jeans were another prevalent style in the 1950s. These jeans sat at or above the natural waistline, accentuating the torso and creating a more polished appearance. High-waisted jeans were typically worn with shirts tucked in to showcase the waistline and create a clean line.

List of Common Styles:

– Straight-leg jeans
– High-waisted jeans

Popular Colors and Washes of Jeans in the 1950s

In the 1950s, jeans primarily came in classic denim colors such as indigo blue. However, there were also some popular washes and variations that added variety to men’s denim wardrobes during this era.

Indigo Blue:

Indigo blue was the most common color for jeans in the 1950s. This deep blue shade was achieved through traditional dyeing techniques and gave jeans their iconic look. Indigo blue jeans were versatile and could be paired with various tops for different occasions.


Stonewashed jeans gained popularity towards the end of the 1950s. This wash involved washing denim with pumice stones to achieve a worn-in, faded appearance. Stonewashed jeans provided a more casual and relaxed look compared to their darker counterparts.

List of Popular Colors and Washes:

– Indigo blue
– Stonewashed

Iconic Tops or Shirts to Pair with Jeans for a Vintage Look

When creating a vintage-inspired outfit with jeans from the 1950s, it’s important to choose tops or shirts that were popular during that era. Here are some iconic options:

Button-Down Shirts:

Button-down shirts were a staple in men’s fashion during the 1950s. Opt for shirts with short sleeves and a classic collar. Look for patterns such as gingham, plaid, or stripes to add visual interest to your outfit.

Polo Shirts:

Polo shirts were another popular choice for casual wear in the 1950s. These shirts typically featured a collar and buttoned placket. Choose solid colors or opt for retro-inspired designs like color blocking or contrasting collars.

List of Iconic Tops:

– Button-down shirts (gingham, plaid, stripes)
– Polo shirts (solid colors, retro designs)

Accessories Worn with Jeans by Men in the 1950s

To complete a 1950s-inspired outfit with jeans, consider adding accessories that were commonly worn during that time period. These accessories can enhance your overall look and add an authentic touch.


Fedoras were a popular accessory for men in the 1950s. Opt for a fedora hat made of felt or straw, depending on the season and occasion. Choose neutral colors like black, brown, or gray to complement your outfit.

Leather Belts:

A leather belt is an essential accessory when wearing jeans in a vintage style. Look for belts with simple buckles and avoid overly embellished designs. Brown or black leather belts are versatile options that can be paired with various outfits.

List of Accessories:

– Fedoras (felt or straw)
– Leather belts (brown or black)

Hair Styling to Complement a 1950s-Inspired Outfit with Jeans

When aiming for an authentic 1950s look with jeans, consider styling your hair in a way that complements the overall aesthetic. Here are some popular hairstyles from that era:


The pompadour hairstyle was iconic in the 1950s and often associated with rebellious youth culture. This hairstyle involves combing the hair upwards and away from the face, creating height and volume on top. Use pomade or hair gel to achieve a sleek and polished look.

Slicked Back:

For a more refined look, you can opt for a slicked-back hairstyle. Apply some hair product to damp hair and comb it back towards the crown of your head. This style works well for shorter hair lengths.

List of Hairstyles:

– Pompadour
– Slicked Back

Footwear Styles Commonly Worn with Jeans in the 1950s

The choice of footwear is crucial when completing a 1950s-inspired outfit with jeans. Here are some footwear styles commonly worn by men during that era:

Leather Loafers:

Leather loafers were a popular choice for both casual and dressier occasions in the 1950s. Look for loafers with minimal detailing and a classic silhouette. Brown or black leather loafers can be paired effortlessly with jeans.


Brogues were another stylish option for men in the 1950s. These shoes featured decorative perforations and a wingtip design. Opt for brown or black leather brogues to add a touch of sophistication to your jeans outfit.

List of Footwear Styles:

– Leather loafers (brown or black)
– Brogues (brown or black)

Famous Icons and Celebrities from the 1950s as Fashion Inspiration for Men’s Jeans Outfits

Looking to iconic figures from the 1950s can provide inspiration for creating authentic and stylish jeans outfits. Here are some famous icons and celebrities whose fashion choices can guide your outfit selection:

James Dean:

James Dean was a cultural icon known for his rebellious style. He often wore jeans paired with white t-shirts, leather jackets, and boots. Take inspiration from his effortless coolness when putting together your own jeans outfit.

Marlon Brando:

Marlon Brando was another influential figure in 1950s fashion. He popularized the “bad boy” look, often seen wearing jeans with a plain white t-shirt and a motorcycle jacket. Emulate his rugged yet timeless style when creating your own jeans ensemble.

List of Famous Icons:

– James Dean
– Marlon Brando

Tips and Tricks for Achieving an Authentic and Accurate 1950s Look with Jeans

To achieve an authentic and accurate 1950s look with jeans, consider these tips and tricks:

Research Fashion Trends:

Take the time to research fashion trends from the 1950s to understand the overall aesthetic and specific details to incorporate into your outfit.

Shop Vintage or Vintage-Inspired:

Look for vintage clothing stores or online platforms that offer authentic 1950s jeans or vintage-inspired pieces. This will help you achieve a more accurate look.

Pay Attention to Details:

Focus on small details like cuffing your jeans at the ankle, tucking in your shirt, and choosing accessories that were popular during the era. These details can make a significant difference in creating an authentic 1950s look.

List of Tips and Tricks:

– Research fashion trends
– Shop vintage or vintage-inspired
– Pay attention to details

In conclusion, by incorporating key elements of 1950s fashion into their wardrobe, men can effortlessly achieve a stylish and timeless look with jeans.

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