Why You Shouldn’t Worry About “Trying Too Hard”

A number of months ago I signed up on Reddit and began responding to questions related mostly to menswear and fatherhood.

I did it because I wanted to expand the reach of this site, but I also wanted to keep my ear to the ground when it came to what men were concerned about regarding clothes.

I wanted to see what kinds of questions were being asked by people who weren’t necessarily “into” menswear. Like, what do normal people (as in, people aren’t obsessed with clothing, like me) worry about?

It turns out, one of the most common questions I see posted by young and not-so-young men alike is “how do I look good without looking like I am trying too hard?”

“Trying too hard” is the subject of today’s article!

It always strikes me as so strange that men have such an aversion to looking like they are trying to look good. After all, the effort is the whole point, isn’t it? I wrote an article not too long about it.

Part of that fear is the fear of looking effeminate. I also wrote about that when I talked about how the term “metrosexual” essentially ruined a generation of dressers. Basically, we were all conditioned to believe that caring about how we looked made us “less than” men.

The problem I see with the concern over “trying to hard” is that it, unfortunately, isn’t without merit, it is just misunderstood.

Let me explain…

The fear over looking like we are trying too hard can be boiled down to this… “I want to be attractive to women, but women won’t be attracted to me if they think I am too focused on my appearance, therefore I will not put any effort into how I look.”

The problem here is that woman actually DO like it when men make an effort to look good. If a woman does her makeup and puts on a nice dress for a night out, you better believe she wants to see her man in a tailored suit.

The effort a man puts into looking good conveys maturity and confidence. It signals that he knows the rules of polite society. It shows he’s been to enough cocktail parties, upscale restaurants, and important work meetings to know how to appropriately conduct himself.

That life experience and self-assuredness is attractive to women.

A confident man knows that he needs to put some effort into his appearance now and again.

But there’s a limit.

Yes, women like it when men take their appearance seriously. But it stops being attractive when it crosses over into fussiness.

Putting on a suit for a nice occasion isn’t “trying too hard”. Spending an hour getting ready because you’re obsessively trying to figure out the perfect tie-and-pocket-square pairing IS.

Women find it sexy when a man can get dressed quickly and with little fanfare. After all, you’ve done it plenty of times before. There should be no preening or primping. You shouldn’t be hogging the bathroom mirror.

When you both walk into a venue, your wife or girlfriend wants people to look at HER, not you.

And you know what? You should want that, too. You should WANT to fade into the background and let the beautiful woman on your arm take center stage. That’s maturity. That’s confidence.

That’s attractive.  

“Trying too hard” in the mind of a woman isn’t a man who takes pride in his appearance. It’s a man who is too anxious to relax when faced with the prospect of putting on something more than a t-shirt and cargo shorts, so he makes whatever scenario he is dressing for all about him.

That lack of confidence is not attractive. And THAT’S what is means to “try too hard”.

Wearing a tweed jacket to work because you like it isn’t “trying too hard”.

Now, is there an element of stereotypical gender roles baked into all of this. Of course. When I was talking with my wife about this article, she said that women definitely view it as feminine if a man is too focused on his looks. She said women want to feel like THEY are the pretty princesses, not their men!

In my article about what women want to see you wearing, my wife said that what makes classic menswear so appealing to women is the unmistakable manliness of it all.

That shouldn’t be all that surprising. And it really shouldn’t be all that offensive either. After all, don’t we men like it when we see women in stereotypically feminine attire? Aren’t we drawn to women in dresses, high-heels, and makeup? Things that accentuate their femininity, the same way tailoring accentuates our masculinity? Don’t we appreciate when we see women wearing those things because we think, “Wow, she really put in a lot of effort to look good!”

It’s the effort we appreciate, right?

And here’s the trap about worrying about “trying too hard”. That “effortless” look everyone seems to want only comes with practice. You HAVE to try pretty hard to look good for a while before you arrive at the place where you can dress confidently and have it appear effortless. We all had to go through that weird, awkward, sartorial adolescence in order to feel good in our own style.

If I never “tried” then I wouldn’t be good at dressing now. I had to try hard for a while until I got good at it. It’s the same with anything. It doesn’t just happen by accident.

Don’t be afraid of being obviously intentional with how you dress. Don’t worry about drawing attention to yourself (within reason, of course).

If you never try, you’ll never succeed. The people who are all weird and judgy about how others dress are just projecting their own insecurities onto you. I don’t want to have to shoulder everyone else’s issues, do you?!

Worrying about trying too hard will never make you a better dresser. You’ll always be wallowing in mediocrity and fear. You’ll never truly enjoy dressing. You’ll never appear confident and capable.

When you buy someone a present, even if the present itself isn’t a winner, doesn’t the recipient appreciate the fact that you got them anything at all? It’s the same with dressing well. The effort you put into dressing yourself is a sign of respect to other people. Those people see and appreciate the effort, regardless of the actual result.

In time, that effort will translate to capability and eventually confidence and mastery. At that point, you won’t have to worry about going overboard (into the fussy fastidiousness I described earlier) because you’ll have the experience under your belt to understand how to do it well.

But you can’t get there without trying first.