Outfit Of The Week 8/24/25 – 8/30/25
This is going to be a weird one…
Recently, my wife and I took the kids to one of those old-timey villages where people in costumes weave baskets, show you how a forge was used, and stuff like that. We’ve been many times and the kids always have a blast. This time there was some entertainment, too. There was a musical group singing sea shanties and a comedy troupe consisting of performers dressed as pirates.
During the pirate show, they selected a few kids from the audience to serve as helpers. Some held flags, others donned fake beards. My boys were able to participate which pleased them immensely.
At one point, the pirate captain came into the crowd and selected me to be part of the show. Whenever an adult is selected to be in a kid’s show, you know the adult is going to play the part of the fool. Apparently, in order to perform my role satisfactorily, I needed to wear a comically small pirate hat and big, ladies’ bloomers adorned with pictures of kittens.
Naturally, this is not the kind of outfit I usually feature in this space. The reason I wanted to include it, though, is to remind you to not take yourself too seriously and not get too wrapped up in your appearance to the point of rigidity.
We’re all human, aren’t we? Don’t we have all our own insecurities? Even though we like to dress well, don’t we get self-conscious about our appearance? Sometimes dressing well is even a mask for those insecurities.
As I mentioned in my “Trip-And-Fall” article, sometimes guys who dress well get a little too particular about how they are perceived in public.
But I warn you against being so uptight about how you look or what you’re wearing that you can’t take part in something unexpected or a little off-beat, especially if it will make your kids happy.
My sons got such a kick out of seeing me do something ridiculous like this!
It’s important that your kids see Dad laugh at himself now and then. They need to see how a man graciously takes a joke and how a man handles possible embarrassment in front of a group. Sometimes you need to play along for the kids.
This is similar to the message in my bathing-suit-themed “OOTW” from a couple weeks ago… your kids need you to show them that you are comfortable with yourself and in your own skin. In that article, I said that your kids should see you shirtless at the beach sometimes since it reinforces healthy body image. In the same vein, agreeing to get up in front of a crowd of strangers and do something silly is also beneficial… it shows that you’re a confident man who can roll with unexpected twists.
All things considered, though, this is probably the last time I’ll feature an outfit that includes novelty, women’s underwear.
Probably.
Have a wonderful weekend!
