Outfit Of The Week 6/8/25 – 6/14/25

The outfit I am choosing to highlight for this week’s edition of “OOTW” was the result of trying to figure out how to dress for two wildly different events in the same day!

The first event of the day consisted of a lovely breakfast at a nice hotel restaurant with my wife and in-laws before attending an end-of-year ceremony at my oldest son’s school. The second event of the day was an outdoor community picnic at my younger son’s school.

The latter event was MUCH more casual than the former.

So, the challenge was how do I dress so I look appropriate for the morning while not looking wildly out-of-place in the afternoon?

Here is how I handled it…

For the morning, I decided that a jacket was in order. The day was warm and very humid, so I opted for a wool/linen/silk blend sport coat from Brooks Brothers and a pink, gingham linen button-down shirt.

I considered a tie, but decided against it as the shirt’s collar is a hair too tight to comfortably wear a tie with it. The pocket square I chose was a brown and blue square that pairs nicely with the pink shirt.

I decided to wear khaki pants and burgundy loafers.

Now, the outfit was perfectly fine for the morning but how did I alter it for the afternoon? I’ll have to just TELL you about it since I didn’t actually get any photos. I am sure you can imagine it.

I obviously doffed the jacket. But I also unbuttoned the shirt a bit and rolled up my sleeves. I could have untucked my shirt, too, as the hem of that shirt isn’t too long but I decided to keep it untucked, however disheveled it looked. Come to the think of it, the fact that it ended up being only partially tucked probably added to its charm.

The khaki pants looked perfectly at the picnic, since they look perfectly at home nearly anywhere you go.

I DID cheat in one area, though. I ended up swapping out my loafers (and removing my socks) in favor of boat shoes. I didn’t know if the picnic would be muddy, so I tossed some knockabout shoes in the truck before leaving the house, just in case.

Overall, I think the day was a success despite the fact that I accidentally splattered hollandaise sauce all over my front about five minutes into breakfast. And the kids weren’t even with me at that point!

I try not to let stuff like that get to me, though. When you’re into menswear like I am, people expect you to be fussy and go all to pieces if something messes up your outfit, so I think it’s important to show that that stuff doesn’t bother me.

After soaking my napkin in my water glass and applying it to the affected areas, the stains were hardly visible. I actually checked my jacket this morning and I couldn’t even locate where the stains were originally, so I think I am in the clear.

That’s all for now. Stay tuned for next week when I feature what I will wear on Father’s Day!

Have a wonderful weekend!