Outfit Of The Week 10/15/23 – 10/21/23
Here we are, thankfully, at the end of another long week.
Today in our OOTW series, I will break down a very casual outfit I wore to a local fair this past weekend. Some of you might have seen this on Instagram already (@father.style) but I thought it was worth it to break it down in more detail in this space.
The reason I am choosing this outfit is because I think it provides a good example of how a casual outfit doesn’t have to be thoughtless or sloppy. When we internet clothing weirdos usually speak of “casual” clothes, we usually talk about things like oxford shirts, loafers, and tweed jackets.
“Guys! I went super casual today and wore a wool tie!”
**cue gasps**
Basically, I wanted to highlight a put-together casual look that is actually, you know, CASUAL. That is, casual to normal people, not “casual” as it’s defined by people like me who spend way too much time thinking about clothes.
The setting this weekend was a fair not too far from my house. Where I live is pretty rural so there are always fairs this time of year with vendors selling things like handmade cutting boards in the shape of moose or fancy bars of soap that could be mistaken for exotic cheese.
The weather was overcast but not rainy. Not too cold, but definitely jacket weather (unless you ask my sons, in which case it was WAY too hot for a jacket, Dad!).
The centerpiece of the day’s outfit was my black, Schott Perfecto, motorcycle jacket. I have a handful of casual jackets in my rotation when the weather isn’t too cold but I could easily wear just this one forever and be just fine. I’m actively trying to wear it as much as I can before the winter hits because it won’t be warm enough in about another month. I’m also trying to get used to seeing myself in it.
I’ve written before about how sometimes we have pieces in our wardrobe that require a little “practice” before we are totally comfortable wearing them. With this jacket, I definitely feel a little self-conscious at first when I step outside wearing it since it’s such a statement.
But then I realize that no one actually cares at all! One time I did have an older woman comment to me that I looked like I was headed to my motorcycle. I said, “Nope! Just to my sensible family vehicle!”
She laughed. I laughed.
Anyway, my point is that the insecurities we feel about wearing what we want to wear are stupid and pointless. Life is too short. Enjoy your clothes.
My Perfecto was one I spotted through Huckberry some time ago (although I don’t believe it’s still offered through their site). I loved the look of the red, plaid, flannel lining against the black leather. Happily, my wife bought it for me as a birthday gift back in 2021. It’s, by far, the most expensive thing in my wardrobe BUT I will wear it for the rest of my life! It’s exactly what you would want in a leather jacket. It’s heavy and fragrant and makes a ton of noise when you move. I love it.
Under the jacket was my L.L. Bean organic flannel shirt in a black and grey buffalo plaid. I did a comparison of this flannel shirt against one of my Lands’ End Flagship Flannels some time ago. This shirt is a great choice for a flannel, as it’s thick, soft, and fits well (provided you have your fit dialed in with L.L. Bean, which is always a struggle).
My pants were an old pair of Eddie Bauer jeans. This is actually the only pair of blue jeans that I own. I am this close to getting a new pair. Not sure from where yet. I need to find a pair that has a sufficient number of belt loops.
As you can see, these jeans are very well-worn. There is actually a rip in the knee that I may patch if I don’t find a satisfactory replacement pair soon. I don’t want to go into the winter months with holes in my pants. Where I live, that’s a recipe for extreme discomfort!
Now, onto my boots. Oh, Redwing Iron Rangers! You’re just as uncomfortable twelve years on as you were the first day I bought you!
Jokes aside, this day was probably the best instance in which to wear these boots. I wasn’t walking too far (mostly just standing around drinking beer watching my sons play in the grass), and I wasn’t on pavement. Also, the grass was dry which meant I wasn’t going to slip.
All in all, it was the perfect time to wear my handsome yet completely impractical boots.
And they DO look handsome, don’t they? Especially paired with the black Perfecto!
To top things off, I wore my black and grey, plaid, wool and cashmere, six-panel cap from Capas via JJ Hat Center in NYC. This hat is a little sleeker than my usual brown, herringbone, newsboy cap and sometimes I like the change in silhouette.
As you can see, this is a very casual ensemble, but it’s not “hoodie and sneakers” casual. It’s still sharp. The key to achieving that is to anchor your outfit with classic, high-quality pieces. In this case: the jacket, the hat, and the boots.
Casual, but intentional.
Have a wonderful weekend!
