Outfit Of The Week 8/31/25 – 9/6/25

Well, summer is unofficially over. Labor Day has come and gone here in the US and the kids are back in school.

It’s always a bit of a shock to the system getting back into the swing of the school year. I don’t know about you, but my mornings are pretty rushed. Not crazy, just rushed. That means that I often fall into the trap of “throwing on” whatever I can find in the moment to head out the door to bring my boys to school.

That’s not really a bad thing. Since I think about clothes a lot, I usually have a pretty good idea of what I am going to wear each day.

But what I discovered recently is that I have a pretty predictable uniform for this time of year, and a representation of that uniform is the basis for this week’s “OOTW”. The “cool-in-the-morning-but-warm-in-the-afternoon, gotta-get-out-the-door-quickly, might-need-to-run-some-errands-while-the-kids-are-at-school” time of year.

Oh, and I also like to do pull-ups in a local park near my son’s school after I drop him off in the morning.

My uniform for this time of the year when the kids go back to school and it still feels a little like summer, but also a little like fall, consists of some faded jeans, boots, a polo shirt, a Harrington jacket, and a cap of some sort.

I swapped out my summer boat shoes for boots since the grass in the park can be cold and wet at that time of the morning when I’m exercising. And yes, I do pull-ups in boots. When it gets colder, I’ll also wear a sweater while doing them!

The jacket and cap are because of the temperature fluctuations throughout the day.

The reason for the polo shirt is that I want to look put-together when I drop my son off at school. I could wear an oxford shirt, but doing pull-ups in a polo shirt is more comfortable. It’s weird to think about, but I don’t think I have worn just a t-shirt out in public since… I can’t even remember when!

This all reminded me of an article I wrote a while back about appearing more stylish than you think you are. Thinking of your outfits through that lens allows you to feel happier about what you’re wearing even on the days when you felt like you just threw something together.

On days like this one, I definitely don’t feel as “dialed in” style-wise as I do when I’m going out with my wife or heading to the office. But my outfit is still classic and functional and allows me to feel like I put a decent, if not my best, foot forward.

There’s a long school year ahead of us, gents!

Have a wonderful weekend!