@George Noulas I would immediately agree for a wholecut or simple cap toe in black. For a two-tone with full brogueing, I might at least consider it, especially since it's blue. And FWIW, I wear black derbys with jeans...and basically nobody I meet likely knows the difference between derbys and Oxfords (but there's a difference between getting away with wearing something and it being good style).

@Kirk Blanchard Correct, that's my understanding. Here's an article I read recently that discusses many details. Tl;dr, holes in shoes were originally designed to allow water to drain after being out in the wet Scottish and Irish boggy areas, hence more a country thing than a city thing. https://www.gentlemansgazette.com/brogues-shoe-guide-men/

Oh, pocket square. It matches belt, shoes, and accents in the shirt, was the thinking.

@Michael McDonnell Ahhhh...<LIGHT BULB> I think I get it now. You need a contrast with the jacket if you want the color to stand out, but then it also needs to complement the jacket color. And then the tie and shirt are the closest in space and can more easily play off of each other. Pants are farther away, but they make up the next biggest total area, so they are maybe relevant too. The concept of pocket squares is still a bit new to me (though I have owned this one for decades), but I just got my first white PS delivered in the mail this afternoon 😄

Who made the hat? I have one from Brooks Brothers that looks identical. Sounds like an exciting trip, enjoy!

The belt ties it together. The socks are a nice touch.

Time for the real important work now.