Outfit Of The Week 12/17/23 – 12/23/23

The outfit you see here in this week’s edition of “OOTW” is actually my second-string outfit. My first idea was to use an outfit from last Saturday, which happened to be my wife’s birthday.

I bought her a really nice black watch dress from British Retro and she wore it all day while we sipped martinis and ate brie while the kids played. To honor the occasion, I wore black watch, as well (in trouser form, not a dress) and a cardigan, striped tie, and navy blazer with gold buttons.

Alas, I didn’t really snap any good pictures of myself that day, so I had to go with the outfit you see here for this article.

Unfortunately, I didn’t get too many good pics of this outfit while I was wearing it, either. Oh well. Sometimes life is a little too busy to even snap some half-decent selfies.

I’ve been thinking a lot about comfort when it comes to classic menswear. I wrote an article this past summer about how classic menswear is actually quite comfortable and no less comfortable than modern clothing like sweats and hoodies. And because I want this site to be a practical resource, I want to highlight, as much as I can, how to be comfortable in handsome, traditional menswear.

This ensemble was probably one of the most comfortable outfits I could have patched together from the existing items in my closet.

The centerpiece of the outfit was my lovely, cream-colored, Supima cotton, cable-knit cardigan from Brooks Brothers.

This sweater was a gift from my wife many years ago and it was one of my first really nice pieces of clothing. I loved this sweater so much that she actually bought me another one just like it, only in blue (which I will likely showcase in the coming weeks).

I love the fit of this sweater. It’s roomy and loose but definitely not sloppy looking. Sure, the sleeves are a little long (no shirt cuff shows when I wear it), but I don’t need to fold back the cuffs at all. I’ve actually done that in the past, but I really dislike the way that feels.

The pockets on this sweater are a huge plus. Nice, secure pockets on a cardigan are almost an adequate substitute for the pockets on a sport coat.

Under my sweater, I wore a navy, herringbone, flannel, button-down shirt from Lands’ End. This was gift from my in-laws two Christmases ago and it’s a fantastic middle option between a true OCBD and a more conventional flannel shirt. It can pretty easily be worn under a rough tweed jacket and look perfectly at home.

Moving on down, for my trousers I wore my grey, wool/poly blend trousers from The Territory Ahead. These pants are so soft, they feel like sweatpants. They are quite thick, though, which was nice when I was sitting outside in the cold supervising my sons while they went around the yard hitting ice with sticks.

I actually wasn’t wearing any socks that day. I didn’t need to since my boots were my waterproof, fur-lined Uggs. I’ve mentioned these boots before in this space and I know it will garner some eye-rolls, but guys, seriously, don’t sleep on Ugg when it comes to winter boot options. I have had these boots for many years and they have faithfully served me through many long, cold, wet winters.

My jacket was my trusty leather flight jacket from U.S. Wings. I’ve been wearing this jacket much more this year and I’m thankful for that. I bought this jacket years ago to celebrate getting a new job, so it has a lot of sentimental value. I went up a size since I wanted to layer a bit underneath it and I’m glad I did. It’s a great “shell” for the colder months when I’m wearing a thick sweater. Nothing cuts the wind like leather!

To top it all off, I wore my grey, wool, herringbone ivy cap that you have all seen numerous times already.

I’ve realized with this “OOTW” series, that I am going to be repeating a lot of signature pieces in my wardrobe, like my Harris Tweed sport coat, my leather jackets, my caps, and my sweaters. At first, I thought this would be a bad thing and you guys would get bored of seeing the same things. But I think it’s actually good to show, not only how to style the same things in different ways, but to see those same pieces in many different scenarios. Remember, one doesn’t need new stuff all the time to get immense joy from clothing. That’s something I hope comes across in these articles.

Next week’s article will definitely be about what I wore on Christmas. I can’t wait!

Have a wonderful weekend!