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Casual Dress for Men – Embracing Effortless Style

CEO Tinh Phung
Do you ever find it easier to look good in a suit? Well, you're not alone. With a trusted tailor and a little investment, pulling off a stylish suit is a breeze. But when it...

Do you ever find it easier to look good in a suit? Well, you're not alone. With a trusted tailor and a little investment, pulling off a stylish suit is a breeze. But when it comes to casual dress, things can get a little tricky. Unlike a suit, casual attire requires mixing and matching different garments, leaving no room to hide behind a tailor.

In the past, suits were the go-to attire for men. However, with the changing times, fewer people are required to wear them for work. As a result, men are now focusing more on their casual clothing. With numerous business casual and smart casual dressing guides out there, it's easy to feel overwhelmed. But fear not! There are plenty of ways to look stylish even when there are no dress codes to adhere to.

A History of Effortless Style

The origins of casual dress for men go back to the stylish 1950s. After World War II, teenagers in the UK and America sought to break free from the austerity of conflict and the rigidity of corporate attire. They turned to a new way of life, rejecting suits in favor of jeans, freedom, and rock 'n' roll. Influential films like "Rebel Without A Cause" and music stars like Elvis Presley and Little Richard played a significant role in shaping this rebellious style.

Marlon Brando in The Wild One (1953) Marlon Brando in The Wild One (1953)

The most iconic takeaway from this era is denim jeans. Originally designed for gold miners, jeans were reborn in the '50s as a symbol of casual and anti-conformist fashion. Since then, they have remained a staple in every decade, evolving in various styles and fits. Jonathan Cheung, SVP of Levi's Design, explains that jeans became popular among biker gangs post-World War II. The spirit of freedom and rebellion spread to rock 'n' roll, catching the attention of Hollywood and iconic figures like Marlon Brando.

What Defines Casual Dress for Men?

The first rule of casual dress today is that there are no rules. You have the freedom to wear whatever you want and still be considered "casual." However, this lack of direction can make it challenging to stand out in a crowd. While many men opt for the typical jeans and untucked shirt combination, truly embracing casualwear requires a bit more effort.

Furthermore, the idea of casual dress has evolved over time. With the decline in the popularity of suits, fashion brands have recognized that casual clothing is where people are spending their money. This shift has led to luxury fashion houses like Gucci, Dior, and Prada entering the streetwear market, collaborating with other brands and reacting to the latest trends.

Mr Porter x Vive La France Mr Porter x Vive La France

However, you don't have to buy into the hype to dress well casually. In fact, that's the beauty of casual clothing – you can look great on a budget. While the rules of casual dress are not set in stone, here are some starting points to inspire your casual style:

The 6 Rules of Effortless Style

Pay Attention to Fit

Just like with tailored clothing, fit is crucial when it comes to casual attire. While there's been a shift towards looser styles in recent seasons, finding a fit that flatters your body shape is still essential. Whether you prefer slim or relaxed cuts, the right fit can make a substantial difference in your overall appearance.

Modern Fit And Casual Men

Know What You're Comfortable In

There's no point in investing in the latest streetwear trends if you don't feel comfortable wearing them. It's important to wear what feels right for you. Confidence is key, and if you feel self-conscious, it will show. So trust your instincts and choose pieces that make you feel at ease.


Keep It Simple

While loud logos and oversized statement pieces might be on-trend, simplicity never goes out of style. Easy, straightforward garments combined together can create an effortless and cool casual look. Look to brands like A.P.C., AMI, COS, and Arket for inspiration on minimalist, well-made clothing.

Mr Porter x Vive La France

Details Are Key

Even the simplest outfit, like a denim jean and T-shirt combination, can be worn in numerous ways. Tucking or half-tucking the shirt, rolling or leaving the sleeves, and choosing the right fit of jeans can make a significant difference. Pay attention to these subtle details, as they can elevate your casual style.

Gieves & Hawkes

Find a Uniform

While some may see the idea of a "uniform" as stifling, it can actually simplify your dressing routine. Just like wearing a suit, finding a casual uniform can save you time and effort. It could be a rotation of navy trousers, white Oxford shirts, and white sneakers or a preference for black jeans and a leather jacket. The key is to establish a go-to combination that reflects your personal style.

Mango Man

Nod to Trends, But Stay Classic

Casual style is heavily influenced by trends, both on the high street and high end. While it's tempting to chase after the latest fads, it's important to choose pieces that will stand the test of time. Investing in classic staples like a bomber jacket instead of trendy one-hit wonders ensures that your wardrobe remains versatile and timeless.

Comfortable Casual Dress For Men

6 Key Casual Pieces

Of course, you can always experiment and wear whatever you feel suits you best. Casual style has no limitations, so feel free to mix and match to discover your unique look. However, if you're unsure where to start, here are some classic casual garments that are sure to impress:

Denim Jeans

Denim jeans have been a staple in casual wardrobes since the 1950s. They offer endless possibilities for off-duty looks. While their popularity has never waned, there has been a rise in artisanal denim in recent years. Brands are using high-quality raw denim and traditional production methods to create jeans that will withstand the test of time.



The humble T-shirt has come a long way. Today, it can be worn with anything, even tailored pieces. Look for good quality cotton and a flattering cut. For a touch of uniqueness, go for a thin Breton stripe or a knitted version. The options are endless, and the right T-shirt can elevate any casual outfit.


Understated Trainers

The luxury sneaker market has experienced tremendous growth in recent years, making trainers a versatile and coveted shoe style. Even traditional shoemakers have had to adapt to the demand. Trainers are no longer limited to sportswear; they can be paired with more formal attire to create a cool juxtaposition. Opt for classic white trainers or choose off-white or contrasting styles for a unique touch.

River Island

Lightweight Jacket

A lightweight jacket, such as a denim trucker or a bomber, can add personality to your casual look. These versatile outerwear pieces have been favored by style icons throughout the years. Look for well-made options that will stand the test of time. Remember, investing in quality outerwear will pay off in the long run.


Versatile Knitwear

A loopback sweatshirt or thin Merino knit is the perfect in-between layer for cooler days. Opt for classic gray or off-white colors for a timeless look. For a hint of sophistication, choose a knitted polo. These easy-to-wear pieces can be paired with various outfits, adding a touch of effortless style.

Simple Casual Dress For Men

A Backpack

When it comes to carrying your belongings, the backpack has become the new norm. It offers practicality and functionality, making it an ideal choice for casual dressing. Whether you prefer a full leather or cotton canvas design, aim for simplicity. A well-chosen backpack can be used for multiple purposes, from work to weekends and even city breaks.

Selected Homme

Remember, casual dress is all about expressing yourself and feeling comfortable in your own style. Whether you choose to follow these rules or create your own, the key is to enjoy the process and embrace the effortless and relaxed nature of casual fashion. So go ahead, explore your options, and let your personality shine through your casual attire!