Outfit Of The Week 1/26/25 – 2/1/25

As I mentioned in my last “OOTW” article, my wife and I just celebrated our ten-year wedding anniversary.

To do a proper celebration, we decided to do an overnight at a local hotel while my in-laws graciously watched the kids.

Man-oh-man, did we have a blast!

As you guys are well aware, my wife and I have always loved going to nice restaurants. That was a key aspect of our personalities before we had kids and we made sure not to lose that when we became parents.

So, whenever we get the chance to go have a nice meal, we jump on it!

For our child-free, gastronomic romp around town, I opted for the three-piece, tweed suit my wife bought for me for my fortieth birthday this past summer.

Some of you might remember that I wore this same suit on Christmas. This time, though, since we were going out to nice restaurants instead of just staying home (like we did on Christmas), I wanted to up the formality slightly. To do that, I wore a silk, burgundy tie with small white dots, a white, French-cuff shirt, and a pair of silver-and-mother-of-pearl cufflinks my wife just got me as an anniversary gift (which I forgot to get a picture of).

Yes, my wife is an excellent gift-giver.

Normally, I would wear this particular shirt/tie/cufflink combination with a more formal, dark, worsted suit. Also this tie held some negative associations for me as I once wore it during an all-nighter at a particularly toxic office. But an event like your ten-year anniversary is a great opportunity to erase all those bad associations!

As I mentioned on Christmas, I can’t get over how amazingly comfortable this suit is. I do wear it with suspenders, not only because suspenders are more comfortable than belts and do a better job of holding up your pants and keeping your shirt tucked in, but because I was wearing a vest. I periodically see men wearing a vest with their belt visible below it. The reason the vest is also called a “waistcoat” is because it’s supposed to cover your waist the same way a cummerbund does when you’re wearing a tuxedo. That means the waistband of your pants should be covered by the vest and the only way to ensure that is to wear your trousers with suspenders (because then your pants won’t slide down the way they do if you’re wearing a belt).

For my footwear, I wore my brown Beckett Simonon Dunham Derbies. These shoes are a nice middle ground between casual and formal and go particularly well with all sorts of business casual ensembles.

The day and night were quite cold and windy so I wore my navy, double-breasted overcoat from J. Crew and my grey, Stetson fedora.

I really need to wear this hat more. It was one of my first “proper” hats and I only tend to wear it when I’m wearing a suit. But it’s incredibly versatile and incredibly comfortable. I love how dress-felt Stetsons get so floppy over time!

The gloves I wore were black, leather, fur-lined gloved from Ugg. I pretty much only wear these when I’m wearing this coat so I just keep the gloves stuffed in the pockets.

Lastly, I wore a black, cashmere scarf to keep the wind out.

It was a fantastic day! We hit a few stellar restaurants and bars and popped into a handful of shops. A relaxing a truly memorable celebration, indeed!

Have a wonderful weekend!