Why Simplicity Is So Important In Menswear

For some men, classic menswear has the reputation of being “boring”.

Because of that, it seems that a big hurdle for men when it comes to dressing well is their perception that wearing classic menswear will somehow erase their personalities.

They feel the need to “express themselves” and they don’t feel that classic menswear, whether it’s a suit, a sport coat and khakis, or even a white t-shirt and jeans, does that (and remember, classic menswear includes both formal AND casual clothes).

Strangely, some of those same men will insist that their usual hoodies and sneakers much more adequately express their personalities, even when most guys out there are wearing some variation of the exact same thing.

The trap these men fall into is expecting their clothes to do all the talking. They want people to know they like a certain band, or they want people to know they are fans of a certain sports team, or whatever. Or, they feel that they have a quirky/dark/spunky/alternative/etc personality and want that communicated through their clothes.

What those guys miss is the fact that…

Your clothes shouldn’t be the most interesting thing about you.

Classic menswear is familiar. It’s not going to shock anyone. It’s usually not going to catch anyone’s eye. It doesn’t announce itself. It very well could make it so the individual fades into the background. When done well, people say “he looks good” without really being able to put their finger on why.

No one is going to know what band you like or what sports team you support from your classic menswear. No one is going to know what your personality is, beyond the perceived traits that your particular outfit conveys, like maturity, trustworthiness, or status.

In your classic menswear, you very well could be viewed as a “regular guy” or even the dreaded “boring”.

But one of the wonderful things about classic menswear is that it’s a blank canvas. The simplicity of classic menswear allows one’s personality to shine through. It doesn’t get in the way.

Paradoxically, the simplicity of handsome, masculine, understated, classic menswear causes it to stand out! Or, more accurately, it causes YOU to stand out.

Classic menswear is the elegant platform that allows your personality to shine.

Readers of this site know that my outfits are often very simple. I wear the same things over and over again. I don’t get particularly creative. I don’t mess with the winning formula. I go years between buying new things.

There is beauty in the stripped-down nature of classic menswear.

The “boring” that so many men see in classic menswear is actually the point! Where they see “boring”, I see functionality, subtlety, and practicality.

They think they’ll be viewed as boring. I think they’ll be viewed as capable and responsible.

Take a look at some of my outfits over the years. They usually consist of fairly plain pants, a collared shirt, and maybe a jacket if I am headed to the office or something…

Outfit Of The Week 4/12/26 – 4/18/26 – Father Style

Outfit Of The Week 8/3/25 – 8/9/25 – Father Style

Outfit Of The Week 6/29/25 – 7/5/25 – Father Style

Outfit Of The Week 2/25/24 – 3/2/24 – Father Style

Could I spice things up with Gurkha trousers, a graphic t-shirt under my jacket, or lapel pin? Of course. And there is nothing wrong with those things.

But the understatement of my outfits is part of what makes them appear so easy and comfortable.

So, how does one get the point where they feel comfortable allowing their clothes to fade into the background? How does one feel ok appearing “boring”?

Well, having an actual personality is a good start.

Ok, that sounds a little harsh, but the reality is that the personalities so many men want to preserve with their hoodies and sneakers are not all that deep to begin with.

Liking a certain band isn’t a personality. Being a fan of a particular sports team isn’t a personality. “I just want to be comfortable” isn’t a personality.

Confidence and comfort with yourself are incredibly important. A while back, I wrote about how I felt like my clothes were the best thing about me when I was mired in an incredibly toxic work environment. In that instance, I basically lacked confidence. I poured all my self-worth into being good at my job and when I wasn’t, my sense of self was shattered. At that point, all I had to cling to was the fact that I knew how to put an outfit together.

My clothes were the most interesting thing about me. Now I realize how important it is to have many layers to myself.

I know that sounds obvious, but at that time, I didn’t spend my time doing anything other than trying to be good at my job. I was so nervous and unsure of myself that I became the “Suit Guy”.

My clothes did all the talking.

That’s why now I am so comfortable being “boring” with my clothes. I have grown into a much healthier version of myself so I don’t feel the need to be “interesting” with my clothes. I don’t feel the need to communicate my personality with my clothes because my personality is no longer that thin.

The bottom line is that your clothes shouldn’t BE ABLE to communicate your personality. Your personality should be so layered and nuanced that any item or genre of style couldn’t possibly contain it all.

Look at someone like Paul Newman or Miles Davis… or your own grandfather. Super cool guys, right? Yes! But they dressed simply. Lots of oxford shirts, sweaters, and roomy chinos. Lots of what many modern men would call “boring”. But those guys were anything but! Their coolness wasn’t so much in their clothes, as it was in their personalities.

So… read books. Exercise. Take walks in the woods. Listen to strange music on the radio. Go see cheap theatre. Cook unfamiliar vegetables. Try painting a picture or writing a poem. Take an intro jiu-jitsu class. Pick up an instrument.

Put down the video games. Get off social media. Ditch the porn. If your time is spent on those things, then no wonder you feel like you need to have your clothing be the most interesting thing about you.

Bottom line, don’t view the simplicity of menswear as a drawback. View it as a way to allow other people to see the wonderfulness that is you.