Having “Fun” With Menswear

The concept of men having “fun” with what we wear is a little sticky for some men.

I mean, isn’t it usually women who have fun with what they wear?

A FUN dress. A FUN bag. A FUN hat. FUN shoes. Wearing something with the express reason of having fun seems to be the realm of the fairer sex.

But menswear is different! Sure we can have a little fun with our pocket squares or, God forbid, our socks. But those instances are described as “adding personality”, which sounds much more dignified than “having fun”!

No… men do not have FUN with our clothes! Our clothes are used to communicate power, authority, maturity, responsibility, success, and trust. There is no room for frivolity in menswear!

In all seriousness, having fun with what we wear can feel very uncomfortable for men. I know it does for me, sometimes.

Why is that?

I think part of the problem is our (men’s) desire to not draw too much attention to ourselves. That’s one of the biggest hurdles we men face when trying to improve our style. We are afraid of people looking at us, judging us, and laughing at us.

I think men worry about looking silly. Respect and admiration are very important to us, so wearing something for “fun” is scary. We don’t want to do anything that could possibly undermine that respect or admiration.

These fears are valid. And I am not here to tell you to completely disregard them (or try to). There are people who say “Well, I don’t care what anyone thinks! When I get dressed, I do it for ME and not for the opinions of others!”

Those people are full of it.

I’ve written before about how people who boast about not caring about what others think actually care very much that others perceive them as people who don’t care about what others think.

I AM going to tell you that there are certain times of the year when you CAN have a little more fun than usual without looking silly. Think Christmas or New Year’s Eve. No one is going to bat an eye if you wear loud, embroidered pants, or a patterned jacket on those days.

July 4^th is also one of those times! Luckily, it’s in a few days!

It’s our family’s tradition to attend the local parade every July 4^th. I’ve also started my own sartorial tradition of wearing my boater hat to the parade. I figured that there is no better time to wear that hat than on July 4^th, especially since I don’t really wear it any other time during the year.

Now, I’m like most other people and I sometimes feel a little self-conscious when I step out of the house wearing something that’s a bit outside my normal wheelhouse (even though I got some “practice” in the off-season). After all, clothing is a form of communication so, like it or not, we are always “talking” with others when we leave the house, regardless of how formal, informal, or well-thought-out (or not) our outfit choices were on that particular day.

What I discovered, though, upon wearing my boater hat every July 4^th, is that I ALWAYS get compliments. Not only compliments, but people will strike up conversations with me, honk their car horns as they drive past, or simply smile in passing.

These are not reactions I was used to at all and it took some time before I knew how to respond in a not-awkward way.

Contrast that with my wife. She has this one dress that she always wears whenever we take the boys to a zoo (which is fairly often, considering both my kids are obsessed with learning about animals). The dress is flowy and green and has pictures of zebras on it. She looks great in it and it certainly stands out in a crowd! Whenever she wears it she gets compliments every few steps which she breezily and graciously accepts.

I, however, needed some practice before I was comfortable with the notion of being NOTICED for wearing something fun (or for being intentional with my clothing choices).

Now, though, I am much more mentally prepared for people’s reactions when I wear my boater and that has only increased the pleasure I get from doing it.

That’s why I encourage you to do the same! Don’t let the fear of being noticed cause you to miss out on the enjoyment of wearing something fun. After all, we only get one shot at this “life” thing. It isn’t a dress rehearsal! We don’t get a second chance to wear what we want once we get a “little more comfortable”.

I’ve periodically said in this space that, in regards to making bolder clothing choices, that I would rather be remembered as the bold dad in the leather jacket than the timid dad in the hoodie. That same concept applies here. I would rather be the bold dad in the boater than the timid dad in the baseball cap.

Here’s another reason to be a bit more adventurous and wear some fun stuff… your kids will remember it. They’ll remember that dad always wore his boater on July 4^th or his bulldog ties on Thanksgiving and Christmas.

They will carry that adventurous spirit and sartorial bravery into adulthood. They will remember how dad wasn’t scared to wear something he liked. It will also expose them to different ways of dressing which will make them more accepting of the clothing choices of others.

It’s like presenting your child with a wide variety of foods. Even if they don’t like it at the time, it will at least make them aware that it’s normal for people to eat broccoli, tofu, or goat cheese. This will broaden their horizons and help them become well-rounded adults.

So, this Independence Day, take the plunge and wear something “fun”. Maybe that will be a boater hat, or a colorful shirt, or a seersucker suit. Maybe that will be simply a pair of loafers instead of sneakers or a polo shirt instead of a t-shirt.

Take the opportunity to be the cause of someone’s smile.