Outfit Of The Week 10/8/23 – 10/14/23
The purpose of the “OOTW” series is to show how the advice I give on this site manifests in the real world.
The weather has settled down a bit this week, thankfully.
Last week was crazy hot so it was nice to be able to break out some actual fall pieces this week.
The outfit I have decided to highlight this time was an ensemble I wore for parent/teacher conferences and our particular situation provided some fun sartorial challenges.
Let me explain…
Ok, so the weather is pretty cool. Like mid-50s during the day. Great! That means I can wear some tweed and other fuzzy stuff.
I also get to attend the parent/teacher conferences for both my sons. Also great! It gives me a non-work-related excuse to dress up a little bit.
But before our scheduled conference, we are supervising my sons and their friends while they play and rove about in the woods while the other parents have their meetings.
Hmm… this just got a bit more complicated.
I decided on a very subdued version of high-low dressing. The centerpiece of which was my grey, tweed, herringbone jacket from Brooks Brothers. I bought this jacket about ten years ago. It was a random, unexpected purchase but the jacket fit so well in the store, I couldn’t let it go. A decade on and it’s still one of my favorite pieces of clothing.
What I liked so much about wearing this jacket was that I could turn up the collar against the wind. Turning up the collar of your sport coat makes it look a bit more like functional outerwear than a style statement. When I wear a sport coat in this fashion (as outerwear) I tend to forego a pocket square to preserve at least the illusion of rugged practicality.
Beneath the jacket was a charcoal, cashmere, crew-neck sweater from Charles Tyrwhitt. I’m actually not too impressed with their cashmere. It’s a bit scratchy and doesn’t have that incredible cloud-like softness that one expects from cashmere. If you told me this was regular merino wool, I would believe you.
I did get this sweater on a steep discount, however, so it makes a good choice for a sweater to wear around the kids.
Under the sweater was my all-time favorite oxford cloth button down shirt from Lands’ End. This was one of the first “real” shirts I ever bought and it’s still chugging along all these years later. The collar and cuffs are frayed, but I have never lost a button or blown out an elbow.
My pants were a pair of olive, 5-pocket chinos also from Lands’ End. When around the kids, I prefer 5-pocket pants. I find that my pocket knife, loose change, and other things don’t fall out of my pockets quite as easily with 5-pocket pants.
My footwear was where I needed to deviate a bit from expectations. I wanted to make sure I was dressed respectfully for the parent/teacher meeting, but I also needed to make sure I was prepared for tromping through mud while watching the kids of the other parents while they had their meetings.
Enter my burgundy work boots from L.L. Bean. I’ve written about these boots many times before so no need to go into details here.
It’s funny, I often think that I should get a pair of actual “country boots” from a company like Trickers or something like that, only to remember that I already HAVE a pair. Since I bought them from a not-flashy company like L.L. Bean, I tend to think I need to replace them with something of better quality. However, we all know that quality does not necessarily equal value.
To top things off, I wore my trusty brown, tweed, herringbone, newsboy cap. This cap is my go-to three seasons out of the year and I am pleased I get to give it some head time now that the temps have dropped.
All in all, the day went very well. Our meetings with the teachers were pleasant and productive. Obviously, the focus of the meetings were the children, but it’s still important to make an effort when meeting with your kids’ teachers. Like it or not, you represent your family. You want the people who are helping guide your children to feel like the children’s parents are pasted together properly. Being well-dressed encourages people to have a better opinion of you and, by association, your children.
Just like you should take the advantage to give yourself a leg-up in life by dressing well, making an effort with your appearance will indirectly help your kids, too.
Have a wonderful weekend!
