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Just because you’re a man, it doesn’t necessarily mean you know how to dress like one. Dressing like a man should not be considered along stereotypical lines — dressing like John Wayne in a Western or wearing army fatigues. Manliness is not about looking tough–it’s about looking elegant, confident, and strong. The opposite of dressing like a man is looking as if you’re still in college. Dressing like a man is all about making you look like a man of the world.

The Dilemma of the Modern Man

It’s one of the ironic facts about life that men are never taught how to dress up by their fathers. The default idea of dressing up for men is to wear a suit and tie. While this may work if you’re the president, it looks a little ridiculous if you dress up for casual occasions, too. As a modern man, you may face the dilemma of wanting to build your wardrobe, but you’re rather clueless on how to start.

Take comfort in the fact that this dilemma is quite common. You only have to look around you to see that most men are somewhat at a loss on how to dress for casual occasions. They either look overdressed, as if they were trying to model for a fashion magazine, or they go to the other extreme and look as if they picked up something from the Thrift store.

In fact, you’d be quite exceptional if you already had a keen sense of the aesthetics of menswear. In all fairness, you shouldn’t be too hard on yourself for not knowing the first thing about casual elegance. After all, you’ve probably devoted most of your time learning the skills necessary to earn a good living. Cultivating a fashion sense was not something on your list. However, now, you may be at a different phase in your life. Perhaps you’ve found the woman who lights up your life. Perhaps you need to improve your networking skills to build your business. Perhaps you’re now at a point where you’re ready to enjoy a more social life.

Unfortunately, looking for information doesn’t quite do the trick. Nor does it help to visit libraries and bookstores. It’s not due to a scarcity of information. It’s due to an overabundance of it. Moreover, there is not enough redundancy in the information to abstract a few core principles. Worse still, much of this information is conflicting.

How Do You Sort It All Out?

Think of your quest to dress well as similar to becoming a student of the martial arts. When you first visit a dojo and speak to a Sensei about signing up for karate classes, he or she will probably invite you to sit in on a class to make sure that this is something you can commit to doing. As you watch various katas and the many variations possible when it comes to blocks, kicks, and punches, you may feel overwhelmed by the complexity of the whole business. However, if you do sign up, the Sensei will start you off with the fundamentals. You’ll only build up advanced techniques over time once you’re grounded in the fundamentals. Think of building your wardrobe with this analogy in mind.


What to Wear


Consider t-shirts, surf polo shirts and button down shirts. Focus on solid colors before experimenting with patterns. Your first goal is to find the right colors, styles and fit for you.


Again, stay simple. Think of dark blue jeans and camel chinos. Later, you can add variations to the color of your jeans and chinos.

Sweaters and Outerwear

Sweaters can become complicated very quickly. Start with grey V-Neck sweaters before you even think of things like Wind Shredder vests, Westward Long-Sleeve Hooded tees, and Balboa 1/4 Zip pullovers. You’ll need a jacket, too. A Navy blazer one would be a good choice. Finally, get a navy, grey, or brown overcoat for those frosty days.


Loafers work well with most outfits. Leather loafers are dressier than sneakers but can still be considered casual wear. Choose brown loafers if you think they work well with your shirts and bottoms. Brown is a softer, warmer choice than jet black loafers. Black will work best only if most of your clothes are dark.


In line with keeping things simple, consider a leather belt. If you got brown leather loafers, then a brown leather belt will go with it.

Start Small

After looking over this list, you might be appalled at its simplicity. Remember, this does not mean that these are the only clothes you will need for your wardrobe. These are the just the recommended clothes you should start with. The basic idea is to get a “feel” for dressing well. Before overwhelming yourself with the vast amount of colors, patterns, fabrics, and styles available for men, get good at figuring out what you find comfortable and what looks good on you. Start small and then build up.



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