Dress Casually…With Style! Mastering Casual Menswear

Casual menswear is increasingly growing in popularity these days, even among classic style fans. Today, we’re going to help you relax your wardrobe and enjoy dressing casually like a pro, while still looking timeless.

It’s without a doubt that casual style is abundant in the 21st century, with some examples leaving a lot to be desired for the sartorial-minded. I’m not even kidding. A muscle-printed T-shirt is one of the first things that popped up from a simple Google search for casual style. As much as this item baffled us, we noticed something in our search results – not all casual outfit ideas are bad. Well, some of them actually being very wearable within a classic mindset. 

However, this varying level of quality when it comes to casual outfits means it can be very confusing to work out what does and does not look good; also what is and is not acceptable to wear out and about. Therefore, we thought it was high time we put our stamp on the art of dressing casually in the 21st century, all while still enjoying the benefits of classic style.

After all, having a great, elevated, casual wardrobe can be a great social skeleton key nowadays as more people accept casual style as the norm. So, we’re not not saying you should ditch your suits and sport coats. Instead, see this as an opportunity to flex your sartorial muscles while accepting casual style and for the avoidance of any doubt. This is not what we mean when we say “sartorial muscles.”

Why is Casual Style Important?

First up, we need to address the question: why is casual style important? Simply put, we’re not living in a world where more formal attire like suits, ties, and sport coats are the norm. There’s no denying, it’s wonderful fun to look back at a time when suits were considered the everyday norm for many, but the reality is we’re not in a society where dressing up is commonplace.

Of course, there’s nothing stopping you from dressing up and dressing well, and we at the Gentleman’s Gazette will be the first to applaud you when you do. After all, that’s kind of everything we’re about. But, it’s important to realize that going against the grain will get people’s attention, as Raphael explains in our other guide.

So, while dressing up is going to turn heads, does that mean accepting casual style is just following the crowd? In a word: no.

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Mastering casual style is important for a number of reasons. First, most people accept you far easier when you’re dressed casually. Naturally, this is especially true if they’re also dressed casually. There will always be occasions that call for you to dial up the formality – evening occasions like a Black Tie dinner, an important meeting at work, or an official ceremony are a few examples. But, as these typically happen less frequently, it means the majority of our time will be spent around others that are dressed less formally.

We humans still make split-second decisions based on others appearances and dressing similarly to the others you’ll be spending your time with will help them to see you as an approachable, equal peer. Sometimes, this will help you in making both personal and business connections.

Mastering casual style will also help you feel more comfortable. This sentiment can be taken literally and figuratively. Not only does casual style involve more laid-back versions of tailored garments, but it also allows you to feel more at ease with yourself and the situation. We’ll go into more detail about the latter point in just a sec.

For now, it’s hard to see how anyone wouldn’t feel comfy when wearing a relaxed outfit of well-worn denim and knitwear, or cool linen and seersucker.

Another reason for the importance of casual style is that it gives you more freedom. The ability to dress up or down your outfit is a lifesaver.

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Maybe you’ve misjudged the formality of the office party and arrived wearing a tie when everyone else is more at ease. Simply remove your time, and you’re already looking like you belong in the group. This works because of the freedom to make an outfit more casual at a moment’s notice, and it means you get to go more places having mastered casual style.

When is Casual Style Acceptable?

Having explored the importance of casual style, let’s revisit the figurative comfort of dressing down with the question: when is casual style acceptable?

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As we previously mentioned, casual style is increasingly more acceptable in a number of places nowadays. Like before, this may initially feel like a negative thing if you’re a lover of classic clothing, but it’s still actually a positive. You’ll have more options for what you’re able to wear to a greater variety of things. For example, Black Tie usually isn’t required for an evening dinner nowadays, but you can indulge if you want to.

Equally, it’s all right if you arrive in a nice suit and tie combination; something that would have been considered too casual for evening events many years ago is now accepted. This is great as it allows you to enjoy a wide range of activities without feeling the pressure of having a wardrobe full of items for different dress codes that you might experience less than others.

That being said, we’ll always advise against showing up to any event in your PJs, even with a more accepting outlook. Planning outfits for those formal occasions is typically easier as you know you won’t be going fully casual.

So, what about casual dress and other more everyday settings? It goes without saying that, in the home, you have the greatest flexibility about what you wear, so feel free to be as casual as you please. But, do bear in mind that you never know when you might need to open the door to someone.

Raphael, Preston, Nathan, and I have previously discussed our honest, at-home outfits, so if you’d like to see more about what we feel comfortable wearing at home, check out our guide on at-home attire. Even though many of us spend a greater amount of time working from home than in previous years, we all enjoy escaping the house to be out and about.

Public settings offer the greatest variety in terms of the formality spectrum. Running errands may necessitate a more casual look than a city shopping trip, visiting the cinema allows you to be more casual than a theater show might, and a family diner won’t expect you to be as formally attired as going out to a fine-dining establishment.

So, the key lies in understanding where you’re going to be spending the majority of your time when in your casual attire. This way, you can tweak just how casual you want to look. If you’re ever in doubt, we’d always advocate for airing on the side of being slightly more formal as it’s always easier to dress down rather than up when you’ve already left the house.

The workplace is the main area where most of us will spend our time, where the standard of dress will be led mostly by company policy. But, even if you don’t have a dress code outlined by your employer, there’s still a general consensus that will be held by your colleagues. Use this general lay of the land as your compass for what is and is not appropriate within casual clothing. And even with no specific dress code, don’t be the guy in the office who thinks it’s Aloha Friday every day.

So, when it comes to the appropriateness of casual dressing, there are many opportunities to explore the benefits of a relaxed style. Remember, even in the Golden Age of Menswear, casual clothing was perfectly acceptable and often worn more frequently than you might think.

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Mastering Classic Casual Style

So, if you’re feeling inspired to truly master casual style, let’s look at some of the classic wardrobe staples that will help you achieve relaxed elegance.

Pants

1. Corduroys

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Starting with casual pants, corduroys are a great addition to anyone’s wardrobe, they are a unique way to add warmth and texture to your ensemble. But the best part is that many makers are starting to make corduroys available in a five-pocket cut, otherwise, known as a “jeans cut.” The slightly slimmer, more relaxed style is a perfect way to introduce corduroys into your casual wardrobe.

2. Chinos & Khakis

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Of course, chinos and khakis are an absolute must-have for a casual wardrobe. The classic natural tones transcend time to make these pants so effortless. And being made from cotton, you’ll be able to find a pair of khakis or chinos in varying weights depending on the climate you’re wearing them in.

Still too hot for the full-length trouser? Then opt for the short versions to make an effortlessly-elegant, summer ensemble.

3. Denim

And our casual pants list wouldn’t be complete without denim. The trusty casual pants for many years now. Denim has come a long way in recent years. No longer just for farmers or railroad workers. There’s a lot of great quality denim to discover out there.

With a flattering cut and a dark rinse, your jeans will be an elevated take on everyone’s favorite casual pants.

Shirts

1. Flannel Shirts

Preston has spoken before about the virtues of flannel shirts. So, while the red-and-black check carries either hipster or “lumberjack vibes,” there are many more options out there for you to explore.

In our experience, subtle checks and patterns work best. And if you really want to up the ante, go for a solid color flannel shirt where you let the texture do all the talking.

2. Polo Shirts

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Polo shirts are, without a doubt, a favorite when it comes to dressed-down styles. But, it’s important to remember that they’re not all made the same. Similar to flannel shirts, focus on the quality of the garment here.

Solid colors are typically going to be your best friend as it allows the unique pique knit to stand out. Go with a structured collar like a dress shirt to allow your polo to be dressed up with relaxed jackets, too, all the while framing your face in the most attractive light.

3. Guayabera Shirts

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Guayabera shirts may be less common, but are no less stylish – similar to the streamlined sibling, the Cuban, collared shirt. The Guayabera lives in a family of shirt styles that features a unique collar style. The intentionally designed open collar is designed to sit flat against the shirt front, but tall in the back like a regular dress shirt. The result is an elegant, V-shape toward the shirt’s buttoning point – somewhat emulating the flattering lines of a suit jacket.

Featuring a roomier cut, shirts like the Guayabera, the Cuban shirt, and the Hawaiian shirt are all great warm-weather additions to your casual shirt collection.

4. T-Shirts

Classic T-shirts are another item to consider here, and by classic, we mean simple, logo-free, and well-cut. Being the cornerstone of a casual wardrobe for decades, a T-shirt is likely no stranger to you, but it’s getting it right that counts. We suggest sticking to the quintessentially-classic white tee, and I’ll guide you through some of our favorite ways to wear it in our other guide.

Jackets

1. Leather Jackets

Let’s now turn to casual jackets. Leather jackets are perhaps the king of the relaxed outerwear realm. Getting a unique patina with every wear, leather jackets have been worn for decades as a reliably-stylish answer to casual outerwear.

After all, formal overcoats have never looked great with less dressy garments. There are many iconic styles out there, so you’re bound to find a leather jacket that suits you. If you’re looking for some inspiration, Nathan is on hand to discuss different ways of wearing one.

2. Overshirts or Shackets

Overshirts and shackets have also been around for many years, but it’s only recently that they’ve been viewed as serious sartorial contenders.

With the pockets maintaining the functionality of a sport coat, an overshirt allows you to add another layer without worrying too much. If an odd jacket doesn’t fit you well, it’s instantly noticeable. But, an overshirt is designed to fit a little bit looser, so you’re able to lean into the nonchalance of sprezzatura by wearing one over your casual look.

3. Knitwear

If you’re looking for a casual jacket alternative, then you’ll never go wrong with some quality knitwear. Sweaters and cardigans instantly make you feel more at ease due to their comfortable construction, and depending on the fibers used, can be worn in place of your jacket or underneath it.

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Pairing knitwear and classic menswear colors, such as navy, gray, green, and brown, is a surefire way to keep your casual wardrobe as versatile as possible, while aiming for sweaters with a V-neck will allow you to dress them up or down depending on whether you like to add some neckwear to them.

Shoes

1. Loafers

For your feet, you’ll want some casual footwear. Loafers represent the best, all-around casual shoe as the lack of laces and slip-on style make for easy wearing in every sense of the word. Indeed, loafers typically live in the category of summer shoes, along with other casually-acceptable styles, such as boat shoes, espadrilles, and driving moccasins.

All these shoes are considered most appropriate for warm weather wear, but can absolutely be used in cooler climates with the right choice of materials. Think of suede or nubuck, as well as everyone’s favorite penny loafer material, cordovan leather.

2. Dress Sneakers

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Speaking of cordovan, you could also go for a pair of simple dress sneakers like Preston’s, which he showcases in greater detail while giving you the lowdown on horsehides here. But, if cordovan isn’t the material choice for you, think of a classically-styled pair of dress sneakers from calfskin or even canvas.

Having been around for well over a century, sneakers have been worn by many classic style aficionados throughout the years. Much more streamlined than a pair of athletic training shoes, there’s room in everyone’s wardrobe for a pair of sneakers. Some of which will even give you that unique vintage style.

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Accessories

1. Tote Bags

Tote bags are an excellent choice for an easy, on-the-go bag for relaxed excursions, as nothing spoils a casual ensemble more than a smart bag built for business. So, as much as we love our attaché cases for office days, they stay at home when we want to chill out.

2. Newsboy & Pork Pie Hats

Newsboy and pork pie hats are equally great for a laid-back aesthetic. The 8-panel panel or newsboy hat has been a popular piece of chilled-out headwear since the turn of the 20th century, and the pork pie is a far nicer take than the more-commonly-seen bucket hat.

The beauty of both of these styles is that they allow you to incorporate something other than a baseball cap into your casual wardrobe.

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Conclusion

With all these items, there are a couple of things to bear in mind. Any of these items have the potential to be dressier or more relaxed. What you’ll notice is the fewer graphics, logos, and embellishments an item has, the smarter it will look. This is typically a great place to start as you’ll not only build a robust, casual wardrobe, but a versatile one, too – when there are fewer distractions.

For example, let a sweater be plain, simple, and have good quality, and it’ll look far better across the spectrum of outfits. Next, you’ll want to look for the same details you’d focus on in your more formal attire. Think about the quality of materials, construction, and as ever, how the garment fits you.

Applying the same principles from your formal clothes to your casual ones, you’ll continue to look and feel great at both ends of the spectrum. Hopefully, you’ve enjoyed our take on casual dressing through a classic lens.

What are your favorite casual style staples? Did any of them make it onto our list today, or did we leave any of your favorites out? Let us know in the comments below.

Outfit Rundown

So, today, I’m wearing a navy blue, crewneck sweater with a blue-and-white striped shirt; along with a pair of medium-washed jeans, brown chukka boots, and some Fort Belvedere, shadow-striped socks; and I’m also wearing a Ralph Lauren fragrance as well to go along with my Ralph Lauren sweater. Had to go together, of course! Check out the Fort Belvedere shop for socks like these.