Outfit Of The Week 1/4/26 – 1/10/26

I know, I know… this week’s “OOTW” entry is a couple days late.

This week has been VERY busy with work. On Thursday I worked until about 11:30pm and last night I didn’t finish up until about 9:30pm. I am even jumping back online to finish up some pressing tasks once I wrap up this article.

I sometimes feel like my “outfits of the week” aren’t “good” or “special” enough to feature in this space.

Sometimes I don’t wear the kind of stuff that would get me likes on social media. Sometimes the stuff I wear that gets me through the week is just kind of… normal.

But I feel like those outfits are important to feature! It’s important to show how a regular dad looks when he goes about his day.

When men get into menswear, sometimes they feel like they need to wear “nice” stuff all the time. If they like wearing sport coats or ties or sweaters or whatever, they feel like they need to make it an inseparable part of their daily lives.

But that’s really not the case.

Look, I like clothing as much as the next internet weirdo, but I don’t wear my finery all day, every day. In fact, on the days I am running errands or working from home, I am often dressed very casually. As in, jeans and flannel shirts.

But here’s the point… you can still look put-together and respectable even when dressed super casually.

“Casual” doesn’t mean “sloppy”.

Today, I needed to do some things around town. I had to pop over the post office. I needed to drop the trash off at the dump. I needed to grab a few items at the local country store.

I wore jeans (the only pair I have), a wool flannel, logger boots, and a sherpa-lined, Carhartt hoodie.

A long time ago, I wrote an article about my “tools”. These items were the things I use every day that don’t get much fanfare. My Carhartt hoodie should have made the cut when I wrote that article because I use this thing all the time in the colder months.

It’s thick and warm. It’s scotch-guarded so it repels rain. Its hood is extended so it acts as a visor to keep rain off my face. Its pockets have flaps to keep water out. It also has a very convenient interior pocket for my phone.

I’ve had this hoodie for a long time. It used to be my dog-walking layer when our dog was still with us. It’s one of those unassuming pieces that didn’t cost much money and isn’t of super high quality, but filled a vacancy in my wardrobe I didn’t even know I had at the time.

I don’t even really like hoodies, but this one is indispensable.

Getting back to my point about “casual” not being the same as “sloppy”… I wear some form of this outfit often. Again, it’s casual but it’s not thoughtless. I’m wearing a collared shirt. I usually tuck it in. The outfit is classic and its utilitarianism adds to its handsomeness.

So, if you’re just starting out in the world of menswear, don’t feel like you need to make tailoring such a big part of your personality that you feel like you can’t just throw on some jeans now and again.

Remember, even though they are casual, things like jeans, boots, and flannel shirts are still “classic menswear”.

Have a wonderful weekend!