Outfit Of The Week 5/17/26 – 5/23/26

This week’s edition of “OOTW” features what I wore during my youngest son’s birthday party last weekend.

The week leading up to his party was a little dreary, weather-wise. The temps were in the 50s and there was a persistent rain most days. Thankfully, on the day of his party, the skies cleared and it was about 68 degrees and sunny.

Perfect weather!

I opted to wear a navy-and-white striped polo shirt from Charles Tyrwhitt. I have 2 polos (their “pique” polos) and I am quite satisfied with them. I have had them for about a decade at this point and they hold up marvelously. I also like the fact that the fabric is a little thicker than most other polos, which means that it doesn’t look either cheap or like the dreaded “golf” shirt.

My pants were a pair of easy-fitting chinos from Lands’ End (I believe their “Knockabout” line). I have also had these pants for a long time. I used to wear them to the office, but then I realized that they look better when worn casually, so that’s how I style them now. I basically wear them in any instance I would wear jeans.

My shoes were my beloved navy boat shoes from Sperry. I have written about these shoes a lot before and why I love them so much (they were the shoes I had on when both my sons were born). Every year I consider replacing them, but I can never bring myself to. I’ll break down and do it once the outer sole wears through, but I think I have many more years before that happens.

Up top, I wore my cheap-o sunglasses (which are perfect for being around rambunctious kids and hot fire pits) and my Panama hat.

As you can see, my Panama hat is really starting to fall apart. The crown cracked a couple years ago and splits in the straw are starting to appear on other areas of the hat.

This was the first “proper” hat I ever purchased (and it has been on multiple vacations with me) so it has a lot of sentimental value. I bought it from JJ Hat Center in New York City and it’s the “Bogart” model from Capas. I think it cost me $125. I have gotten every penny’s worth!

I also wore my Lorier Zephyr watch for a little touch of class!

All in all, the day was very enjoyable and my son had a great time playing with his friends.

It looks like this coming weekend might bring a return of some cool, rainy weather. I am not opposed to that, though, as I can only stand so much heat before I start to long for autumn.

Have a wonderful weekend!