Outfit Of The Week 5/3/26 – 5/9/26

This week’s edition of “OOTW” features an outfit I wore to a performance of a play my sister was in!

Since it was a live performance, I wanted to wear a jacket and tie to show my respect for the insane amount of work that goes into something like that. It’s also important to demonstrate to the kids how to dress for live theatre, regardless of the size of the production.

The weather was cool and breezy, which meant a thicker jacket was in order. I decided on my grey, herringbone, Harris Tweed sport coat from Brooks Brothers. It’s probably the last time I’ll get to wear this jacket for a few months.

My shirt was a white, twill, French cuff, spread collar shirt from Charles Tyrwhitt. Some people on the internet say that a shirt of this formality shouldn’t be worn with a tweed jacket, but those are silly rules that popped up when the internet became a thing. You can absolutely wear a white, double-cuff shirt with a tweed jacket. My cufflinks were my gold-tone, Irish knots.

My tie was a brown, grenadine silk from Poszetka. I also wore a tie-clip that my sister had gifted me at her wedding many years ago. I actually love wearing tie clips as they are amazingly practical when you’re chasing children around.

My trousers were tan, wool pants from Men’s Wearhouse. Don’t sleep on MW! I have a handful of smart trousers from them and they hold up wonderfully. They are also CHEAP! I got these on a 2-for-1 sale about ten years ago!

I do want to make the point, though, that if I had been wearing tan, cotton chinos, I would NOT have worn the white, French cuff shirt. The casualness of the pants AND the jacket together would have been too much with the formality of that shirt. Since I was wearing tailored, wool trousers, the formal shirt didn’t feel out-of-place.

My shoes were my burgundy, Beckett Simonon Dunham Derbies.

My watch was my Lorier Zephyr.

The theatre was about two hours away, so we got into town early and stopped at a diner so we could stuff the boys with fries and ice cream before the show. Thankfully, they were marvelously behaved!

Oh, since I know you’re curious, we dressed the boys in polo shirts. We wanted them to be comfortable, but they also wanted to “dress up” like us.

All in all, it was a busy day and an incredibly enjoyable performance!

Have a wonderful weekend!