Outfit Of The Week 2/16/25 – 2/22/25

This week’s edition of “OOTW” features an outfit from a belated Valentine’s Day date with my wife.

While we still celebrated V-Day on Friday by exchanging gifts, the day was very busy with work and child-pickups. We were also planning on doing a lot of driving early the following morning to visit my wife’s parents, so we made sure to keep the evening short.

As I always make sure to mention, my in-laws are incredibly gracious to watch our boys while my wife and I go out to dinner. We try our best to not take advantage of their kindness by keeping our evenings out a reasonable length of time and not come home too late.

As I mentioned last year, I always keep a jacket at my in-laws’ house so I don’t have to travel with it. That jacket is a very light, unlined blazer from Suit Supply.

It’s perfect for warm weather, but not so much for February. To combat that fact, I wore an undershirt underneath my regular shirt for some added insulation (which proved useful as our dinner table was situated near the door of the restaurant).

My shirt was a striped, spread-collar shirt from Charles Tyrwhitt. My tie was a burgundy grenadine (also from CT).

The older I get, the more I realize how LITTLE a man actually needs in his wardrobe. Honestly, I think I could live the rest of my life with only two ties… a burgundy grenadine and a navy grenadine.

The trousers I wore were a pair of tan, wool trousers I bought some years ago from Men’s Wearhouse. I got these tailored a long time ago at a crappy dry-cleaners and they made the legs two different lengths!

I haven’t made the time to get them fixed and I imagine I am the only one who ever notices it. The pictures I took really highlight the difference. I still wear the pants, though, as it doesn’t bother me all that much.

My shoes were the Bass Weejuns I’ve shown a million times. I’ve noticed that after a few years, these shoes are getting a bit more comfortable. They were always a little stiff and tight, but they seem to be loosening up. I only paid around $100 for them so I think I’ve gotten my money’s worth at this point.

We had dinner at a nice hotel restaurant and then had a cocktail in the bar area and listened to some live music. It was a very nice evening, although something strange happened while we were having our after-dinner drink…

Sitting next to us was a pair of very drunk older women who were constantly getting up to dance to the music. This was a very nice bar and the ambiance was definitely not a “get up and drunkenly flail about” kind of vibe.

At one point they tried encouraging my wife and me to get up and dance with them to which we politely declined. At that point they seemed to get angry and started shouting at us that we needed to loosen up.

Now, I know that it’s common for stupid people to get even stupider when they drink, but their disdain for us, I believe, was based more on how we looked than the fact that we didn’t want to dance with them.

I don’t think they liked that we were dressed nicely.

That’s something I am sure many of you have experienced and I experienced it a lot when I first got into classic menswear and was hyper-aware of the opinions of those around me. It’s unfortunate, but sometimes you’ll encounter people who automatically dislike you because they believe that you think you’re better than them because of how you dress.

Unfortunately for them, they immediately reinforce that belief by being judgmental and rude.

Those two women provide a real cautionary tale, if you ever needed one: don’t ever become the rude, sloppy folks in the bar who are too drunk to read the room and realize that everyone is staring at them.

Anyway, despite that very weird interaction, we still had a great evening.

Have a wonderful weekend!