If you want to take the next step towards being the best man you can be, you need to stop being afraid of style.

I’m not about to say you need to get in touch your feminine side, or have to get a hard on shopping for shoes, none of that crap. But too many men are scared to the point of inaction from cultivating their own style.

When I talk about fear, I’m talking about:

  • Fear of wasting money on something they will never wear.
  • Fear of looking or feeling stupid.
  • Fear of making a mistake, a lack of confidence.

As men do, we rationalize these fears, often to the point of absurdity. We hold on to shoes, holes worn through the sole, because they’re comfortable. Our single formal outfit no longer fits, but look at what great shape it’s in!

We scoff at men who talk about fashion, as only pussies care about shoes or the cut of a jacket.

At the end of the day these are all excuses to avoid accepting the fact you are too scared to make a change, to risk a small failure. When you get dressed, you should look great, feel great, and be comfortable. With the occasional exception (sometimes the situation will force you to discomfort, like a formal wedding, in Arizona, mid July) there is no reason you should have to fall short on any one of these.

What is Style for a Man?

When it comes to being a real man, style is the combination of three f’s: functionality, fit, and fashion. They are all important, but some more so than others. As a man, the most important, bar-none, is function.

Functional Style

When it comes to style, in many ways we are lucky to be men. Functionality is frequently low on the list of priorities in female fashion, but for men it’s paramount. The more functional something is, often the more fashionable it will be as well. The only real exception to this is technical clothing. Sure, your gore-tex Arcteryx jacket is the most functional shell money can buy for winter outdoor survival, but it has no style value.

Excluding the trends, style hasn’t changed all that much.

What I mean by functionality in style comes down to something you should always keep in mind when planning a purchase: BIFL — buy it for life.

Your goal should be to buy things that will last for life, or for as long as humanly possible, without straying into the technical or “work” side of things. It’s no coincidence the most stylish clothing from the 70’s is exactly the same as it is now: thick selvedge denim, welted leather boots, horse-hide leather jackets, and wool suits to name a few.

Keep an Eye on Trends

Mentioning clothes from the 70’s is a perfect moment to talk about trends. All items in fashion go through trends, but at the base level of high-quality items, the trends don’t change all that much. If you bought tie-died denim back in the 60’s, the only hope for that having style today is purely nostalgic.

But if you bought simple, raw, indigo dyed blue jeans, they will look as great now as they did then.

When it comes to buying things on trend, you want to keep it to the more exposable items. Buying a trendy T-shirt isn’t a problem, throwing it out in five years is going to be no big deal. Buying a trendy $1,200 leather jacket is a much bigger mistake.

You need to earn that patina

The best looking clothes are the BIFL, rugged pieces, with healthy patina. Faded jeans, well worn boots, wear and creases in your leather jacket. Patina is one of the sexiest things in all clothing, but with two big exceptions:

Spectacular, when earned.

Spectacular, when earned.

  1. It only looks good on clothes built strong enough to look worn, but still be fully functional.
  2. You need to earn the patina.

Pre-faded (or even worse, pre-torn) denim is a crime. It looks terrible, and is a complete waste of your money. Clothing only looks great worn out if that wear has come from your every day life. When the patina on your clothes is from your own wear and tear, it looks and feels like it belongs there.

The creases are where you bend, the worn spots are where you rest your elbows, and the marks on your pockets are the exact size of your wallet. When the wear on your clothes is a result of your life, nothing could look better. When the wear is artificial, it will never look or feel as good as it would have when properly earned.

Price is relative

As you will see repeated with every article later discussed, the price of buying things with great style seems steep up front. But once you factor in the durability and longevity of the items they’re often cheaper than if you had saved a few bucks up front.

Keeping in mind this advice, let’s go over the basics of style, from the bottom up, starting with your new pair of boots.