Classic Men’s Style Simplified: The 5 Step Guide to Dressing Sharp

There are two ways to approach modern male fashion and style: dress to keep up with the latest fads (e.g. flannel shirts or wacky socks), or stick to classic men’s style. I personally think the classic style approach is best, and in this post I aim to show you why. Let’s get started!

Dressing with style changes everything.

Classic men's style: Yves Saint Laurent

“Fashions fade, style is eternal” – Yves Saint Laurent

Well, maybe not everything. Still, becoming a well dressed man will change how society perceives you. Some typical consequences of looking sharp:

  • You will get more attention (and compliments), especially from women
  • You will hear smart ass comments from guys who can’t (or won’t) dress well
  • You will feel more confident and at ease (this effect may be permanent)
  • You will develop an appreciation for others who make an effort to look good

The list goes on. The effects are multiplied in North America, where the bar for men’s style is set very low.

It is actually not surprising that most men have no idea how to dress – it is a classic case of the blind leading the blind. Most guys will copy what their friends are wearing, happy to fit in and not attract any unnecessary attention. Some go one step further, emulating looks on billboards or in men’s lifestyle magazines. Others try to show off with luxury brands. A few give up entirely.

It’s not hard to dress well. It certainly requires far less money than most assume. However, it requires some patience and a willingness to try something new. Just as with any major undertaking, the first step involves a change of mindset.

Step 0: Becoming comfortable with the idea of dressing well 

You have to convince yourself that it’s good to dress well. This is very important. Become comfortable with the idea of permanently changing how you look. Give yourself the permission to reap the rewards.

Additionally, realize that there is a big difference between fashion and style. Fashion is about showing off the latest in designer trends, while men’s style rarely changes over time. The goal is not to have the clothing do the talking for you. Instead, the idea is to find and develop your own image. A way of showing the world who you are, even before you do or say anything.

Finally, you must also understand that this is a life long project. One does not become stylish overnight. It is a learning process, and it will take time to work out the details. But there are rewards at every step of the way.

Step 1: Making the most of your physique

As a general rule: the more fit you are, the better most clothing will look on you.

You have heard it all before. If you are overweight, work on slimming down. If you are underweight or skinny, work on gaining some mass and build muscle. A good ideal to aim for is the classic v-shape: at least a 10 inch “drop” between your chest and waist measurements (for example, a 42 inch chest and 32 inch waist size). This is not easy, but it can be done if you keep up a good exercise routine and make sure you are eating healthy.

Perhaps the biggest advantage of a toned body is that it simply can’t be faked. It is not something you can buy. By staying fit and healthy, you give yourself a tremendous advantage.

Classic men's style: Marlon Brando

Marlon Brando in “A Streetcar Named Desire”

While working out is a process of building up, the next stage of the style journey involves elimination.

Step 2: Eliminating the unnecessary

There are many traps on the road to dressing well. This includes clothing you are tempted to buy to keep up with fashion trends. It also includes clothing that should have become unpopular long ago, but for one reason or other has survived in popular culture. Common traps include:

  • White socks. There is almost no reason to own any, unless they are ankle socks you wear while exercising. Keep it simple: match socks to the color of the pants (or a shade darker). I highly recommend replacing old ones with Darn Tough socks – they’re tough as hell and have a lifetime guarantee.
  • Torn or patterned jeans. Completely unnecessary. Keep it simple: stick to dark (preferably unwashed) denim. If you’re in doubt, you can’t go wrong with the Levi’s 501s (clean rigid).
  • Graphic tees. These are back with a vengeance, and signal instantly that the wearer has no interest whatsoever in dressing well. They are distracting and juvenile.
  • Running shoes, flip flops and boat shoes. There is a time and place for all of these. Respectively: while exercising, hanging out at the beach and while on an actual boat. Outside of the environments they were designed for, all three options look downright tacky.
  • Anything with visible branding or logos. Perhaps the most common trap of all, since it is so hard to find undecorated clothing. Still, the truth is that brands, company names and logos only serve to distract. Avoid being a walking billboard.

There are many more examples, but this is a good starting list. To dress well, you must avoid wearing tacky or distracting clothing. The best way to protect yourself from committing major style crimes is to give all unnecessary clothing away. Failing that, lock it up and use it only for the activities it was made for (e.g. boat shoes for maintaining grip while sailing).

As you do this, you will start to see what is a good piece and what isn’t. And in most cases, throwing out the unnecessary will you with little else to wear. Which is why the next step is so important: rebuilding your wardrobe with what works.

Step 3: Training your eye and rebuilding the wardrobe

Congratulations. If you’ve made it through to this stage, it means you’re serious about looking good.

You now have to build your new wardrobe almost from scratch:

  • Get the best looking shoes you possibly can. Unless they are sneakers, aim to spend 200$+ on a pair of decent shoes. Avoid square toes on dress shoes or loafers – look for round toes and a leather (not rubber) sole. Good American shoe manufacturers: Alden, Allen Edmonds.
  • Stick to the most versatile men’s items – dark blue denim, button-down shirts shirts, solid trousers, v-neck tees, grey or navy sport coats, and two-button suits (charcoal if it’s your first suit). Variations of these will be more than enough for a good wardrobe.
  • If you are not sure of which colours work best on you, try sticking to earthy and subdued tones: light or dark greys, blues, browns. Try mixing it up with deep purples and burgundy. It’s easier to make outfits work with these than with blacks, whites, yellows or bright greens.
  • Avoid buying anything with visible branding or logos. Look for pieces that will look good in any outfit – don’t expect luxury names alone to do the work of putting together a solid outfit.

Above all, think of the whole outfit when buying individual pieces. A versatile wardrobe built from quality clothing will give you many combinations to work with, so you can mix it up all the time.

These are good starting points, but there is much more to style than simply following heuristics of color and patterns. Get inspiration from legendary style icons. Do some research and find images of Steve McQueen, Paul Newman, Tom Ford, Bob Dylan, Johnny Depp looking their best. Or watch an episode of Mad Men.

Classic men's style: Steve McQueen pulls off the turtleneck

Steve McQueen pulls off the turtleneck

As you look around and notice who’s doing it right, you will realize that there’s an important step missing.

Step 4: Mastering fit 

Everything must fit well. This is non-negotiable, and a cornerstone of classic men’s style.

  • Finding a good tailor should be your first order of business. Most decent dry cleaning places will also do alterations – check the prices and read reviews. Send in one shirt for alterations to begin with. If it’s a good place, stick to it.
  • Shirts should not puff out at the waist. Pants should not require a belt (or suspenders!) to be held up. Suits should fit like a glove – at the very least, alterations will be necessary for any suit bought off the rack.
  • Pants (including jeans) should not be baggy, or skin tight either. Aim for a “slim straight” fit.

There are many more considerations, especially when it comes to dress shirts, suits and pant lengths. These are details a good tailor can help you with.

At this point, you are ahead of 99% of the competition (unless you live in Milan). You have experimented with what works for you, and you have started to personalize your clothing by making it fit to your body only. It is likely that you now own (and use) a tape measure. There’s really only one stage left.

Step 5: Setting your own style 

The real fun begins when you start breaking the rules.

You no longer need inspiration or help from others, although you certainly won’t refuse it.

You start introducing your own ideas and modifications, and start seeking out individual items that you know would work great in your wardrobe. Chances are, you are already somewhat of a style icon in your local community or social circles.

You say “to hell with guides, I’ll make my own.” And you start wondering how you can give back.

Classic men's style: Yves Saint Laurent

Once you have your own style, you can break the rules


Leave a comment