How to Dress Smart Casual (Elegantly & Classy), Men

How to Dress Smart Casual Men

Looking like an adult in a suit and tie is extremely simple, but doing so in a casual outfit is a completely different matter.

When worn by men of all ages, how can you take these timeless casual essentials like jeans, t-shirts, and sweatshirts and make them age-appropriate?

There are several ways to do this incorrectly, but the worst one is for an older man to look to be trying too hard to look younger.

How do you do it? How to look adult-like while wearing casual clothing.

There are seven things, in my opinion, that you should focus on. There are several important guidelines to follow and some incredibly easy improvements you can make. In this article, I’m going to share them with you.

Keep Things Simple

I want you to start by recalling how you used to dress when you were younger, perhaps when you were in high school.

Rock band t-shirts, t-shirts with sayings, and sweatshirts with logos were among my favorite clothing items to wear frequently. I used to often wear this denim jacket that was covered in patches and pins.

I’m going this to say that you shouldn’t wear logos, graphic t-shirts, or other items like that. That’s not exactly what I’m saying.

If you wear graphic t-shirts, ironic t-shirts, and logos as you get older, you will not look your age.

However, I want to draw attention to the fact that everything there merely seems to be very busy. It’s better to keep things simple if you want to dress like an adult and wear t-shirts, sweatshirts, and jackets.

Opt for a solid-colored t-shirt rather than one with graphics. Choose a classic style without a logo rather than a sweatshirt with a large logo.

It’s casually simple, which is one of the secrets to looking good in simple adult clothing.

Proper Fit

The next thing you should pay attention to when dressing casually as an adult is something I often stress when it comes to looking good in a suit: your clothes need to fit.

It doesn’t matter if it’s formal or casual.

You won’t appear mature if your clothing doesn’t fit. You won’t appear as if you know how to dress for your age.

One thing about fit that I want to make clear is that your body type and the look you’re going for actually determine how your clothing should fit.

If you’re anything like me and think of your personal style as classic with a modern sensibility, a slim, comfortable tailor fit that is definitely neither tight or form-fitting is probably what you’re searching for.

There is nothing that says you can’t keep up with trends as an older guy if it is something you enjoy doing occasionally.

But I’d just advise against going overboard.

But how do you truly make your clothes fit properly?

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The first thing I would suggest is to find a really good tailor. even for casual attire.

Any number of minor things, such as shortening a shirt sleeve or hemming your pants or jeans, can be made by a good tailor. These adjustments will go a long way toward helping you make off grown-up casual successfully.

The second thing I’d recommend is to investigate a variety of various ready-to-wear companies. The fitting of different brands vary. Some of them will be effective for you and some won’t. You will be well on your way once you determine what works and what fits your personal style.

Create Your Own Personal Uniform

There are many various ways to dress casually and look good as an adult, which is something I want to emphasize throughout this article.

I don’t want you to get the impression that I’m telling you to dress like me in order to look good or appropriate.

Each of us is unique; we all have distinct lifestyles, occupations, and life experiences.

About six or seven years ago, I experienced a minor crisis. I believed that I needed to wear something new all the time. To continue proving to everyone that I knew how to dress.

But what actually happened was that I started getting frustrated and started driving myself crazy. In all honesty, it was too difficult, and I didn’t feel like myself.

I then became really at ease with the notion that this was my style and recognized what I actually liked to wear.

I learnt to actually like and respect what I like to wear and stopped basing my style decisions on what I observed other people do.

Knowing what you like and sticking to that and developing a sort of uniform for yourself, that’s not boring, that’s cool.  It defines who you are. It serves as both your identity and your style card.

Simplifying and paying attention to fit while going what I’ve already talked will work in a variety of various styles and approaches.

But it’s crucial that you feel at ease because discomfort will have a detrimental impact on your confidence and how you handle yourself. All of that work would be useless at that moment.

Upgrade Your Jeans

Let’s discuss some particular improvements you may make, starting with one of the most important casual wardrobe essentials: jeans.

It’s time to invest in some new, properly fitted jeans if your old ones are worn out, full of holes, and either saggy or overly long, pooling at your ankles.

You might be wondering how many pairs and what colors of jeans you should own.

You need a slim and dark pair as your first pair. It will be one of your most versatile pairs of jeans in your entire collection and your go-to pair for work.

Depending on your employment, you can wear them in more dressy casual settings like a date night or even business casual. They can also be worn casually and ruggedly.

A pair of black jeans is the second pair I recommend. Black jeans undoubtedly have that rock and roll vibe, but as you get older, they have some other qualities that are, in my opinion, advantageous.

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With just a t-shirt and a casual jacket, they look slimline and are very easy to dress up casually.

A pair with a subtle wash is the third pair I recommend. They go well with a variety of shirts, including t-shirts, polos, and button-up shirts, and are sporty and great for the weekends.

Add a pair of white shoes if you feel comfortable doing so. There are many possibilities there, especially during the summer, but I understand that not everyone will be interested in them.

Upgrade Your Footwear

The topic of footwear, specifically sneakers, will be discussed next. I enjoy sporting sneakers just as much as the next guy, but I won’t be sporting a pair of bright sneakers outside of the gym or the garden.

Athletic shoes should never be your default footwear while you’re not working out or doing household chores.

Upgrade to a pair of simple leather low top shoes instead. They still have a sporty vibe, but they make a casual ensemble appear a little more polished and well-planned.

Upgrade Your Outerwear

As you age, you appear more mature, and your casual attire should reflect this.

Upgrading some of those timeless pieces of casual outerwear that you already own in new fabrics, textures, and colors is an easy approach to upgrade this.

Consider the traditional denim jacket. I don’t see anything wrong with wearing this as an adult, but you’re right—it does make you look younger.

However, the identical piece of clothing would look and feel completely different in a light tan corduroy, caramel-colored suede, or chocolate-colored suede. It yet maintains a casual appearance while still appearing more mature.

Have a Sport Coat

Since we’re talking about casual attire, this next upgrade might cause some debate, but I do believe that having a go-to sport coat is crucial for adults, even when wearing casually.

Our objective is to make a casual ensemble appear more put-together and age-appropriate. If you consider an outfit to be made up of three primary pieces—pants, a shirt, and a jacket or other outer layer—all you need to do to dress up a casual ensemble is add one dressier element to the mix. One of the simplest ways to do it, in my opinion, is with a sport coat.

Consider the following outfit: jeans, a t-shirt, and a hoodie. I don’t even need to explain the difference that just one tiny alteration made to the overall look and feel of this outfit when the hoodie was replaced with a navy sport coat.

Casual Outfit Ideas

We’ve talked some broad things you can take as well as some specific improvements you can make, but rather than merely talking it, what I want to do now is provide you with some outfit ideas.

For varied seasons, check out these five casual outfits.

Weekend Ready

The best example of almost everything I’ve talked is this initial look.

Light wash jeans and a light grey hoodie make a classic sportswear combination. I’m wearing a thin navy suede jacket over it. A cropped jacket works really well for a sporty look like this, and the darker color harmonizes and completes the look.

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Simple sneakers in two colors. Sporty with a contrast between the white sole and taupe leather.

Rock ‘N’ Roll

Next, we have a look at vintage rock & roll.

Sky’s the limit when it comes to how you can style this with a black t-shirt and black jeans. I kept it simple, but I used some really stark contrasts.

Starting with the jacket, it has a traditional trucker jacket style but is made of stunning caramel-colored, buttery-smooth suede. The texture and color both enhance the look and make it stand out.

White sneakers add some additional contrast while supporting the outfit. The contrast of white and black appeals to me. Simply put, it adds visual complexity and appeal.

Summer Casual

To show that casual doesn’t always imply jeans, we’ll move on to a summers look. Particularly during the summer, when wearing jeans won’t really be an option.

An easy alternative would be a pair of cotton khaki pants. Going a simple brown gingham button-up shirt. It’s an extremely simple combo.

The footwear and accessories are what really bring it all together and make it look good. Received a pair of suede tassel loafers; again, suede always strikes me as more mature. A matching belt made of suede and a panama hat complete the figure.

Jeans & Sport Coat

The next look is a sport coat and jeans.

Simple tan crew neck sweater and slim black jeans serve as the foundation.

It’s OK to wear something casual on its own, but the brown sport coat adds a whole other level of sophistication.

If you wanted to dress this up a bit, you could easily wear a good pair of walnut derbies, but for a more casual, sporty look, I like the white sneakers.

Summer Contrast

Here, cotton pants in a cream color are used in place of jeans, and I’m wearing a black polo top with them.

High contrast, extremely simple combination.

I purposefully chose not to wear a belt with this to keep it looking simple and understated.

To add some balance from top to bottom, pair this with a white baseball cap and some white sneakers.

The power of simplicity is the main thing I want you to learn from this guide.

Having a large wardrobe shouldn’t be your main objective. The capsule wardrobe concept is a great place to start if your goal is to have less clothing that you can use for more activities.

How to Dress Elegantly Classy Casual  Men


  • Christopher

    Christopher has 9+ years of experience as a creative fashion designer who stays current with the latest trends.

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