How to Rock ‘50s Men’s Style Like a Modern Pro

Certain looks remain timeless—and the refined, rebellious style of the 1950s is one of them. This era’s classic cuts, attention to detail, and distinct silhouettes still have magnetic appeal, embodying a blend of sophistication and nonchalance that resonates with men now. Whether you're a fan of rugged rockabilly or polished Ivy League prep, '50s men's style is rife with wardrobe inspiration.

Prosperity after World War II had men moving beyond practicality, especially as fabric prices went down. This wasn’t just a decade of straight-laced Mad Men types, but also striking individuality from James Dean’s badass denim and leather to Cary Grant’s luxe suits. While their fits might not currently look mainstream (though they're sure to come back again in some way), elements of men’s style in the '50s are quietly making a comeback in certain circles, appealing to anyone looking for a certain timelessness.

Why the appeal? Aren't we done with skinny ties? Yes and no. Right now, ‘50s style is almost an anti-trend—a refreshing contrast to today’s looser, athleisure-heavy wardrobes. Social media has branded it "old money aesthetic," mockingly or lovingly or both. But incorporating these looks can make you stand out without trying too hard. Whether you like a tailored silhouette or vintage accessories (watch obsessives, take note), embracing mid-century influences can root your wardrobe in authenticity. Here, we break down what defined men’s '50s style and how you can rock its essence today.

What Was Men’s Style Like in the ‘50s?

The 1950s were transformative in men's style, blending postwar conservatism with an independent streak. You had clean-cut, tailored looks influenced by military precision—think crisp suits, structured blazers, and high-waisted trousers, all part of a "gentleman’s wardrobe." Celebrities like Cary Grant and Gregory Peck defined this classy look, setting the standard for male elegance. Meanwhile, the Ivy League look, rooted in campus style, featured loafers, chinos, button-down shirts, and letterman jackets—think, well, Ed Helms’s character Andy Bernard in The Office.

But the ‘50s also saw the rise of OG rock 'n' roll culture, introducing a bold, rebellious vibe. This greaser aesthetic, inspired by the likes of James Dean and Marlon Brando, tended toward leather jackets, white T-shirts, cuffed jeans, and combat boots—a style you can still easily find on dudes now. These were essential pieces for the man who wanted to project an untamed confidence. Dean’s role in Rebel Without a Cause immortalized this look, giving men permission to experiment.

Related: I've Wear-Tested Dozens of Leather Jackets. Here Are the Best of 2024

The latest resurgence in '50s men's style isn't exactly a big boom in the way Mad Men parties took hold in the 2000s, but it holds plenty of men who want to look good without necessarily embracing the fast fashion and tech-driven athleisure of the day. Vintage looks like cuffed jeans, leather jackets, and classic suit cuts offer eternal appeal. It's about more than looking retro; it’s a statement that quality, individuality, and classic appeal never go out of style. As Taylor Swift once told us, “You got that long hair, slicked back, white T-shirt.” If you're a man who's tired of fleeting trends, ‘50s style is a great way to explore outfits that have never stopped being cool.

How to Wear Men’s ‘50s Style Now: Tips and Products

To bring ‘50s style into the modern day, the key is to incorporate its timeless elements with a fresh, updated twist—keeping the look refined but versatile. Here’s a guide to channeling ‘50s menswear without looking like you stepped out as Eisenhower from a vintage catalog.

Clothes

Start with the basics: tailored pieces with clean lines are central to ‘50s fashion. Opt for high-waisted, slim trousers—an alternative to the baggy styles of recent years, these offer a more polished silhouette. For a classic look, choose darker shades like charcoal or navy, which can easily be dressed up or down. Pair them with a fitted white dress shirt or a lightweight sweater in neutral tones for a streamlined feel.

For outerwear, consider adding a fitted bomber jacket or leather biker jacket to your collection. These were staples of the ‘50s rebel aesthetic and can lend attitude when paired with modern pieces. Of course, James Dean and Marlon Brando popularized this look, and today, brands like Slowear offer options that will last for years. Just remember it's all about balance. Fold in elements that complement your personal style rather than trying to replicate the look from head to toe (you don't want to do Halloween unless it's Halloween). Instead of opting for a full suit reminiscent of Gary Cooper, take the tailored trousers and mix them with a fitted T-shirt or a contemporary jacket. This fusion allows you to embrace vintage inspiration without appearing like your grandpa.

Slowear Suede Bomber Jacket

Nudie Jeans Lean Dean Grey Steel

Monochrome Navy Double-Breasted Blazer

Slowear Slim-Fit Cashmere and Silk Turtleneck Sweater

Accessories

Accessories bring out the spirit of the ‘50s and add personality to your outfit without necessarily becoming a full commitment. A classic wristwatch—like a stainless steel or leather-banded model—brings sophistication and feels authentically vintage. Avoid digital or overly flashy watches; the goal is to keep it simple and elegant.

For shoes, loafers and brogues that were popular in the ‘50s are easy to incorporate into your wardrobe even now. Loafers work well for a relaxed, Ivy League-inspired vibe, while brogues or even a polished pair of Oxfords can elevate smart casual or business casual. Ryan Gosling’s retro styling in La La Land is a great example, with high-waisted trousers and loafers. It showcases how to effectively channel '50s men's style in today's world. If you're channeling rockabilly, consider some well-structured boots to complement your jeans and leather jacket.

A final touch: sunglasses. A pair of wayfarers or aviators will not only protect your eyes but also add an effortlessly cool touch to your look. Brands like Neven are perfect for capturing that vintage aesthetic without sacrificing quality. Timothée Chalamet has a penchant for vintage-inspired accessories and is often seen wearing statement sunglasses and quirky ties, blending them with modern silhouettes, which is reminiscent of the playful side of '50s style​.

Neven Gold Rush Sunglasses

Vionic Lombard Oxford Lace-Up Shoes

Seiko Presage Cocktail Time GMT Watch

Atlant Helsinki Sunglasses

Le Chameau Explore 7" Low Boots

Hair and Grooming

Hair was an essential part of ‘50s style, and many of those classic cuts are back. The cultural shift of the decade away from wartime austerity fostered a more sophisticated aesthetic. For men, this meant adopting hairstyles that were neat and stylish, often with the use of pomade to achieve slicked-back looks or pompadours, epitomized by figures like Elvis Presley. Think side parts and crew cuts—hairstyles that convey confidence and polish. When creating your best '50s-style men's haircut, a high-shine pomade keeps it modern and controlled. Philip B. Styling Gel is perfect for those looking for a firmer hold as this gel helps achieve the pompadour or slicked-back hair with little work. You can also go for a looser side part if you prefer a more natural, effortless style. For facial hair, keep things minimal and well-groomed; clean-shaven or a short, neat beard is ideal to match the refined, structured aesthetic.

Philip B. Styling Gel

Le Labo Shaving Cream

Le Labo Styling Concrete

Why You Should Trust Me

I have an extensive background in fashion journalism, with experience across various publications such as Vogue, Harper's Bazaar, Business Insider, and MEL Magazine. I bring a thorough understanding of cultural trends and historical contexts that influence fashion choices, especially when discussing classic styles like '50s men's fashion (and yes, I can tell you all about how the look has come back again and again). Additionally, I stay updated on current trends and products, attending fashion weeks all over the world twice a year and providing well-researched insights from the runway. My writing is informed by a keen eye for detail and a passion for helping others achieve their desired looks.

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