The Case Against “Being Creative”

A lot of what I write is in response to a lot of menswear and style content I see, whether that’s other articles or social media posts. Sometimes I feel like I need to push back against the tide of “conventional” menswear wisdom in order to provide you with the highest quality content I can.

Unfortunately, a lot of content out there is lazy.

And I can promise you that I will never post lazy content.

That all brings me to our latest installment of “The Case Against…” series.

We’re all in different places in our menswear journey. Personally, I feel pretty “settled” in my own personal style. I don’t really feel like I need anything else to make my wardrobe complete. I don’t have any real glaring holes in my wardrobe that I am longing to fill.

A lot of content you see will imply that in order to be truly stylish, to truly attain style Nirvana, you need to be “creative”. That content will say that if you are sticking with the basics, you might look ok, but you’re not really one of the truly stylish few. In order to be part of that exclusive club, you need to bend the rules or disregard them entirely (and all that “learn the rules like a professional so you can break them like an artist” crap).

None of that is true.

All across Instagram, I see guys trying their best to be “creative”. I see unbuttoned double-breasted jackets, short shorts, slouchy white socks with loafers, cotton ball caps with suits, loud streetwear, chunky sneakers, belts with off-center buckles, sweaters tied around shoulders, and totes, totes, totes galore.

Now, there is nothing wrong with experimentation. If that’s what pleases you, go right ahead. But don’t think that you NEED to experiment in order to be stylish.

Personally, I don’t like being creative with my clothes. I quite enjoy the simplicity of dressing in a conventional way. I like that there are certain ways of dressing that look objectively good by enhancing the appearance of the male physique and I don’t feel the need to tinker with that. I often wear the same things all the time! Call me boring. Call me unimaginative. But I still have just as much fun as anyone when I get dressed. I still enjoy menswear more than most people. I just don’t feel like the need to break new ground.

Take the aforementioned unbuttoning of a double-breasted jacket. You’ve undoubtedly seen it. This has been one of the internet’s go-to moves in the past year or so to aggressively signal that you’re “in the know” when it comes to menswear. Unfortunately, unbuttoning your double-breasted jacket chucks all the visual benefits of wearing a double-breasted jacket out the window!

Gone are the upward lines of the lapels which create the impression of strong, broad shoulders. Gone is the impression of a trim waist due to the voluminous fabric flapping in the wind.

Instead of looking tall and strong, you’ll look short and dumpy. It’s an example of people who “know” menswear venturing into territory that actually makes them look worse.

Also, I often find that when someone is “being creative” with their menswear, they are trying to make things “work” by combining items of clashing formality levels. Ties with jeans. Baseball caps with suits. Sneakers with tailoring. None of this ever looks good.

If you’re trying to “make something work” it doesn’t work.

I consider myself pretty knowledgeable about menswear and none of that junk is for me. When I get dressed, I enjoy the simplicity of combining everything in a logical way.

Once, many years ago, I was reading StyleForum when I saw a post that featured one of the veteran members (who hasn’t posted on that site in years) wearing a brown tweed jacket with a rather bright blue tie. Most of the responding comments mentioned that he would have looked better had he worn a burgundy tie instead. He acknowledged the wisdom of those comments but then said he considered a burgundy tie but decided against it because it would have been “too perfect”. That’s why he wore the blue tie instead.

Huh?

So, he knew a certain tie would objectively look better given the established conventions of combining color (that we all agree on) but intentionally chose to wear something that looked worse so that he could… what, exactly? Prove that he was truly stylish because he bucked convention?

When bucking convention is done simply for its own sake, what is the point? If you KNOW something looks good, just put it on and go about your life. You don’t need to mess with what works.

For me, when I’m wearing business casual, for instance, I know that a tweed jacket looks good with an Oxford-cloth button-down shirt, khaki pants, tan socks, and brown shoes. When I’m dressed casually, I know a pair of jeans looks good with some dusty boots, a flannel shirt, and a leather jacket. When I’m dressed more formally, I know a suit looks good with black cap-toes, a linen pocket square, and grenadine tie.

These are combinations that don’t need alteration. I don’t need to unbutton my jacket when I’m wearing a double-breasted suit in order to signal to others that I know what I’m doing, sartorially. I don’t need to wear shorts with my barn coat a la Ralph Lauren. I don’t need to layer a denim jacket under my sport coat.

Some of you might feel like you’re not truly stylish unless you’re venturing out into uncharted waters. Trust me, you don’t have to worry. “Being creative” might be some people’s dish of tea but it’s not the menswear endgame many will have you believe it is.

No, the true menswear endgame is simply feeling happy and confident in what you wear. Feeling like what you put on presents you as your best self is the whole point of this, even if that’s not all that terribly original.

Trust me, that’s ok and you’re not alone in not wanting to be creative with your clothing.

You can absolutely be “boring” and “stylish” at the same time.