Outfit Of The Week 9/24/23 – 9/30/23

Welcome to another edition of our “Outfit Of The Week” series!

The outfit I have decided to highlight this week is decidedly more casual from last week’s office attire, as I was working from home the whole time.

Regardless of that fact, I still wanted to look halfway put-together since I am around town fairly frequently.

The temperatures are drifting downward and my attire for this week reflects that.

Just a reminder that I don’t get any kickbacks or commissions for anything I write about or link to.

I started with a burgundy and cream rugby shirt from J. Peterman. I’ve written about this shirt before in last year’s “shirts for fall” article and I have been itching to bust it out of the closet. The cotton is satisfyingly thick which made it ideal for trucking my boys to school on these chilly mornings.

Like it or not, how we look at school drop-off and pick-up makes a difference for how the people who regularly interact with our kids, like school employees and other parents and their children, view us. I’m not saying it needs to be a beauty contest, but looking halfway presentable around others helps to tip the scales in our favor. But you already knew that.

Another thing I really like about this shirt is that the dark stripes hide stains well, which is imperative when you’re wrangling children. I still usually spill something red on the CREAM stripes, though. Let’s hear it for Murphy’s Law in action.

My pants were a pair of Lands’ End Knockabout Chinos in olive. They have a little bit of stretch in them, which I really could do without, given how pants with stretch have a tendency to wear out, but they have held up pretty well over the past three years or so.

I wear these in all the same instances I wear jeans. I don’t treat them any differently than run-of-the-mill dungarees.

What I like the most about them is that they are 5-pocket instead of the slanted pockets on regular chinos. I find that 5-pocket pants are much more practical with kids, since stuff is less likely fall out of the pockets.

Moving on down, I wore my trusty burgundy leather boots from L.L. Bean. I wrote about these in my “quality versus value” article a while back and these boots are still proving to me that it doesn’t always cost a lot to get value.

I’ve had these boots for over four years and I wear them most days. They were pretty cheap so I hope I can resole them when the time comes, although the Vibram sole is holding up fine. I’ve never had a pair of boots with softer leather.

My watch was my 38mm Timex field watch I wrote about earlier this week.

My belt was a beat-up brown leather belt from Fossil. My wife gifted me this belt so many years ago, I can’t even remember how many.

My jacket of choice, which is one of the most important considerations for this time of year, was my navy Harrington jacket from Orvis which I wrote about last year. This jacket is very robust and boasts ample pocket space (two large, flapped, handwarmer pockets and one zippered inner pocket on the left side).

The inner zippered pocket on this jacket is really well done. I’ve had jackets in the past where the inner pocket was an afterthought and it’s either too small or doesn’t secure its contents well enough. With this jacket, I am not afraid my phone will get wet (or fall out) if it’s raining. And it was raining a bit this week, especially in the mornings. It was that invisible, cold, mountain drizzle. This jacket kept me sufficiently warm.

My only gripe with this jacket is that the plaid lining doesn’t extend far enough. I always like the look of the tartan peaking out when the jacket is open, but it doesn’t happen with this jacket. It’s certainly not enough of a gripe to make me want to shell out hundreds of dollars on a real Baracuta, though.

To top things off, I wore my well-loved brown, wool, herringbone, Capas brand newsboy cap that I purchased from JJ Hat Center in NYC about ten years ago. This hat has accompanied me on trips domestic and abroad, as it’s the perfect travel hat. It’s casual when you want it to be. It’s formal (enough) if you need it to be. There’s really no instance in which is doesn’t work.

I feel that this was a good outfit to officially kick off autumn: not too heavy, since it’s still fairly warm in the afternoons, but cozy enough for the early-morning temperature drop.

Have a wonderful weekend!