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What the Best Dressed Men Have in Common

Ever wonder what constitutes “well dressed?” How is it that so many men can wear such wildly different styles of clothing and still be considered well dressed? Why does a three piece suit work for one guy but looks completely out of place on another? How do these guys know what is going to work for them?

We’ll let you in on a little secret: It’s not random. The best dressed men all have certain things in common. We’re going to tell you about those commonalities here, and even more importantly, tell you how you can emulate the success of the seemingly natural trendsetter.

Well Dressed Men Know Themselves

The first thing to understand about style and fashion is that not every style works for every man. The best dressed men know this: they won’t wear tight fitting clothes if they aren’t in good physical shape. They won’t wear pointy shoes if they have disproportionately large feet. It’s unlikely they’ll wear orange if they have a tan complexion. They’ll know their strengths, weaknesses, and everything in between, and construct their entire look accordingly.

Well dressed men have often deconstructed what they see in the mirror down to a science. Then, armed with this personal blueprint, they pick their clothes, accessories, style their facial hair, and put it all together in a coherent manner. This is the first step in knowing how to dress: know yourself.

Here are a few examples of what well dressed men will pay attention to when doing an “audit” in front of the mirror:

  • General Physical Build — Different styles work better for people of different builds
  • Facial Bone Structure — The shape of your face can have a serious impact on how you design your look. For example, a strong jawline is worth accenting with light facial hair or a smooth shave. If you’re bald, either shave it all off or keep the hair you do have extremely short.
  • Leg to Torso ratio — Guys with long legs and short torsos look better in certain clothes than guys shorter legs and longer torsos.

Well Dressed Men Know Their Audience

A huge part of dressing well is knowing what you are dressing for and who you are dressing for. You might look great in shorts and boat shoes, but if you’re going to a black tie wedding no one is going to be complimenting you on your look. Ripped jeans and sneaks might be in for 23 year-olds, but if you are pushing 60, and so is most of your social circle, dressing like this:

Guy wearing ripped jeans
This look can work, but not in a crowd of retirees

Isn’t going to win you any accolades.

Age isn’t the only thing that determines an audience. For instance, different looks appeal to different cultures. A look that’s in with the boys might not be the right thing to wear on a date. And of course, many different “crowds” have a signature look.

If you want to model your look after men who know how to dress, know your audience. Pay attention to what those in your social circle wear, and try to capture the essence of the style (as opposed to copying individual articles of clothing). The clothes we wear are a core component of the first impression we make on others, so we don’t agree with those who say you shouldn’t pay attention to what others may think.

Well Dressed Men Take Calculated Risks

Conformity might be an underrated quality of dressing well, but calculated risk is another. Many men take risks when it comes to style and fashion, but few men take risks that are calculated. Anyone can wear something ridiculous and attract attention. But attention does not equal well dressed (unless your goal is purely attention seeking).

The most effective fashion risks are those that have been meticulously crafted. Usually, these risks are hardly risks at all. They are carefully thought out deviations from the most common way most men in the particular social circle dress. A proper calculated risk should set you apart but maintain a look that overall, still blends seamlessly with the crowd.

Some ways to start:

  • Add an accessory — An unusual watch, bracelet, or necklace can take an unremarkable look and give it a needed spark.
  • Experiment with color — We’re not talking a kaleidoscope here, but deviating from the normal color palette on an item, even if it’s as small as socks, can work.
  • A different cut — A different cut of jeans, pants, or a suit, can make a big difference in your appearance. Going with a slimmer than usual suit, if your physique allows it, is an example of a calculated risk that often pays off.

Well Dressed Men Aren’t Afraid to Change

Nothing that’s in style, stays in style. You can quote us on that. In the 90s, baggy jeans were in, can you imagine that (or perhaps you remember it)? Who knows, in a decade, they may be in again. Well dressed men don’t get married to a particular look. They navigate the ebbs and flows of the fashion world and make the necessary adjustments. Sure, there are staple items that will likely stay in for longer than you will care to worry about, such as the two piece suit. However, you aren’t going to wear a two piece suit all day, are you?

Pay attention to the shifting trends of the fashion world and you’ll be well equipped to make the changes to your look that the trends demand. Paying attention to fashion trends is also a good way to take calculated risks: think fashion sneakers, 15 years ago.

Seek Inspiration, Not Imitation

The purpose of this article isn’t to tell you to seek out a well dressed man and imitate him. The purpose is to seek inspiration from well dressed men, by first understanding the process they go through to dress well. If you know how the best dressed men create their look, then you can use that knowledge to create your own look.

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