Men’s Clothing Essentials That Will Make You Look Smarter

Elevate your style with these men’s clothing essentials. Discover timeless classics for a sharper, smarter look. Upgrade your wardrobe today!

A Man Wearing a Linen Suit

When people talk about ‘great style,’ the references made are often to ‘icons’ like Gianni Agnelli, Cary Grant, Steve McQueen, and so on. Individuals often highlighted wearing suits, ties, tuxedos, and the like. But most of us, I reckon, only rarely find ourselves in situations where we can apply these ‘looks’ and thereby earn the label ‘stylish’ in that given sense.

So, what men’s clothing essentials can one wear to look more stylish without opting for a tuxedo or suit?

The great thing about classic menswear, in my opinion, is that it hasn’t changed an awful lot over time. Sure, there are different cuts for different times. There are fashion items that go in and out of style. But if you stick to the classics, you will have come a long way into timeless and great style.

The challenge, I think, is, that when you think about “classic menswear” you think of the 1960’s uniform of suits and ties. But we no longer live in the 1960s, so how do you apply this to every day?

I have expanded my understanding of classics, which makes it easier to put together outfits that most of us can incorporate into an everyday wardrobe and still look stylish, casual, and authentic. All while using classic pieces.

After all, the classics are classics for a reason.


When it comes to footwear, there are two undefeated champions that you can pair with almost any type of outfit. The results will be considered stylish. I am talking about white sneakers and penny loafers.

White Sneakers

The all-white sneakers are a must have in every wardrobe. Classic, versatile, and can dress up an outfit, just as it can be the casual element. Wear them with anything from jeans to chinos, or let them be the casual counterpart to a pair of suit trousers.

It’s worth mentioning that if you plan to wear a pair of white sneakers with suit pants, it’s advisable to opt for a more minimal-looking pair.

Man Wearing White Sneaker Navy Blazers and Khaki Pants

Penny Loafers

It doesn’t get any more classic than this! I like to use them to level up a casual outfit – think washed jeans, a crisp white tee, or an OCBD (Oxford Cloth Button Down) paired up with a DB blazer or an overshirt.

Men's Clothing Essentials: Penny Loafers


The white tee has been a classic stable for years but has often been synonymous with the tougher looks, paired with jeans, leather jackets, and biker boots – think for instance James Dean, Marlon Brando in “The wild one” or Springsteen in the 1980’s.

What I like about it, is that it can do almost anything in an everyday wardrobe; goes perfectly under a blazer, stands alone with a pair of suit trousers, under is the casual element under a denim shirt or OCBD.

Steve McQueen Wearing Jeans and a White T-Shirt While Riding a Bike
Steve McQueen Wearing Jeans and a White T-Shirt While Riding a Bike

On that note, you can’t get around the OCBD (or Oxford cloth shirts in general) as an everyday capsule item. In most cases, I find these work better than the dress shirts.

Again, we no longer live in the 1960s so very few of us wear suits daily – and in that case, I find the OCBD a much more versatile choice.

Paul Newman White T-shirt and Pants Outfit
The impeccable Paul Newman dressing up in a white tee


When it comes to trousers, a man can work wonders with his outfits. If you get the trousers and shoes right, you can make most outfits look classy, whether you are wearing a T-shirt or an Oxford shirt.


The art of “breaking” up a suit. Spezzato means “breaking” in Italian. Using the jacket from one suit, with the trousers from another; sounds easy, but takes some skills to do right.

However, the ground rules of this I use almost daily. I wear the trousers with an OCBD, a white T-shirt or a turtleneck.

Men's Clothing Essentials: Khaki Pants with Navy Blazer


One of the most important tips when it comes to jeans is to stay away from trends and stick to the classics. Find the perfect fit for you – maybe even invest a bit in alterations if necessary.

Men's Clothing Essentials: Classic Cut Jeans

For some, it’s a Levi’s 511 Slim Fit; for others, it’s a Regular Fit 501. It sounds simple, but when it comes to picking out the right jeans, fit is everything. I recommend sticking to dark blue denim, as it’s easy to incorporate into most outfits, and it’s the most classic of jeans.


Because you can’t go wrong with a pair of khaki chinos. The only danger with these is that you can easily end up looking like most Key Account Managers in the office (white shirt, navy blazer, white sneakers, and khakis).

So, my recommended pairing here would be to opt for a navy blue or light brown turtleneck, a Barbour waxed jacket, and a pair of brown suede loafers.

A Man Wearing Navy Turtleneck with Gray Pants and White Sneakers
Perfectly executed grey chinos with a dark turtleneck

The “Joker” Pieces

There are a handful of men’s fashion items that anyone can pull off. For me, a stylish plain turtleneck, a polo shirt, and driving mocs are fundamental pieces of my daily look.

Turtleneck Sweater

You can’t get around a turtleneck sweater. You just can’t. It’s perfect for casual wear around the fireplace, it’s perfect with jeans and a Barbour jacket, with a suit – full suit or spezzato. Even with shorts and driving mocs as a statement piece.

Again, fit is key and depends on your body type. Find what fits properly for you.

A Man Wearing Navy Turtleneck and Khaki Pants While Drinking Coffee in Kitchen

Polo Shirts

For the casual, yet still stylish twist. A man I find great inspiration from is Stanley Tucci, and few people can dress in a polo shirt like him, so that is actually my recommendation – study Mr. Tucci! Spend a little extra on a good polo, and you will have a partner for life.

Stanley Tucci Wearing a Navy Polo Shirt with Jeans
Stanley Tucci in His Garden, Wearing a Navy Polo Shirt with Jeans

Driving mocs

Driving mocs and this is at my own expense – but a pair of driving mocs is probably the piece that I have had as a stable in my wardrobe for the longest time. I couldn’t imagine not having them as an option – when you want to go a bit more casual than your penny loafer but just aren’t in the mood for sneakers. They are perfect – but that is a matter of taste.

Men's Clothing Essentials: Driving mocs
Brown Leather Driving Mocs Worn with Jeans

White Jeans

Often seen as a fashion item – however, I have taken these into account as well, as undyed denim actually is white – or ecru. Which in my book makes them as classic as regular jeans. I might take a pounding for this statement, but so be it. I can’t imagine a wardrobe without them, as they work with almost everything.

Men's Clothing Essentials: White Jeans
A Man Wearing White Jeans with Blue Denim Shirts

The New Guy

Hi, I am new here on Midway Gentleman. My name is Casper. I am a father of two from Denmark. I am a car enthusiast and a watch guy, and I have a keen interest in classic menswear.

Casper Lundmose Sitting in a Green Porsche Taycan
Casper Lundmose, the writer of this article wearing his signature white sneakers and Levi’s jeans with OCBD shirts

My style is all about mixing classic pieces with modern twists. I like to mix and match classic items like those mentioned above; Barbour jackets, Levi’s 511s, turtleneck sweaters, and OCBD shirts, are my daily go-to’s. In my opinion, the subtle details make the difference in life.

Look out for my future articles on Midway – and please do reach out on Instagram

Men's Clothing Essentials That Will Make You Look Smarter
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Men's Clothing Essentials That Will Make You Look Smarter
Elevate your style with these men's clothing essentials. Discover timeless classics for a sharper, smarter look. Upgrade your wardrobe today!
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Midway Gentleman
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