My wife and I went out for drinks the other night to celebrate the 4^th of July.

Since we were going out to a couple of nice restaurants and bars, and because it was a special day (and because I’m me), I wore a suit and tie. It was very hot over the holiday weekend, as you are all aware, so my suit was seersucker. With the suit, I wore a white shirt with mother-of-pearl cufflinks and a burgundy, grenadine tie.

At the first bar we visited, a guy sitting near us told me that he thought my suit was awesome. At the second bar we visited, another guy complimented my suit. In total, I received 3 or 4 compliments from random men that night.

Even though it made me feel good that other people thought I looked nice, I am not telling you this story to brag.

And despite some suspicions you may have, none of these compliments were in “come-on” form. None of these guys were hitting on me. Actually, every guy who paid me a compliment appeared to be on a date with his wife or girlfriend.

The reason I’m telling you this story is because I have noticed that I pretty frequently get compliments from other men. Sure, I get comparatively more compliments if I’m wearing something “fun” like my seersucker suit or my leather biker jacket, but it also happens when I’m wearing just a regular suit, or a fedora, or a trench coat, or logger boots. Basically, anything that you or I would consider “classic menswear”.

What always strikes me as unusual about those compliments, though, is that they are more-often-than-not accompanied by a bit of a lament or longing. The person giving the compliment will say something like “You look so cool… I wish I could wear something like that.”

Or, “Wow, what a great suit… and here I am in my shorts!”

On the night I wore my seersucker suit, none of the guys who paid me compliments were poorly or inappropriately dressed. They all actually looked very nice! Yes, one guy was wearing shorts, but it was July 4^th and oppressively hot, so that made sense.

My point is that these guys were not schlubs. They were regular dudes who got dressed up a little to go out with their wives on a Saturday night.

But they all seemed to express to me a desire to dress differently. It wasn’t just “You look good”. It was “You look good AND I WISH I COULD DO THE SAME”.

It revealed that, deep down, a lot of men, even if they are unaware of it, long to wear cool stuff like suits and ties. They know it makes them look better. They know their wives will love it. They know that other people will notice them.

But they don’t do it.

The fact that there is something hindering these men from presenting themselves in the way they would like is fascinating to me, because I don’t think those men see it this way.

So many men, when they think of a guy they once saw in a cool suit, think “But I could never wear that” and then immediately stop there. They don’t think beyond it. They don’t think about WHY they feel that they could never wear a seersucker suit to a bar.

In thinking about all the guys I saw out that night, while they all looked nice and put-together, they did all look fairly similar. Interchangeable, even. Mostly polo shirts and jeans or untucked, button-front shirts and khakis. Again, perfectly appropriate, just… safe and unremarkable.

Now, you guys know that I am ALL FOR safe and unremarkable. I actually find there is great power in the safe and unremarkable. But these guys weren’t dressing that way because they liked it. They were dressing that way because they felt like they had to. Like they had no other options.

At that point, “safe and unremarkable” isn’t fun. It’s restrictive. It makes the man feel trapped if that’s the only thing he feels he can wear.

I think part of why men feel like they can’t wear the things they really want to is the fear that people will laugh at them. Or think they’re fake or “trying too hard”. They might even think that caring about how they dress is unmanly.

Unsurprisingly, I have written about ALL of those things before.

But when writing about those things in the past, it didn’t occur to me that these guys didn’t have much insight into WHY they felt like they couldn’t wear what they’d really like to. They just thought that those options were completely unavailable to them for some reason.

Again, the longing is what struck me about their compliments. It was longing bordering on sadness.

It was like they were thinking, “Dammit… I wish I could wear something like that.”

But there is no need for the hopelessness. It’s never too late to try something new. And classic menswear is super accessible. You don’t need a great body or a ton of money. A lack of confidence in any area is dispelled with sufficient practice (I’ve written about that, too).

In writing this all down, it’s now clear to me that there really isn’t any one particular reason why so many men feel that classic menswear is not an option for them.

But for the men who complimented me the other night, I hope I was able to serve as a source of confidence for them in the future. I hope that they’ll be able to think back to the guy in the seersucker suit and gather up the courage to put on something that they’ve always wanted to wear, but never had the courage to.