That’s a weird, but awesome button-less, spread collar polo I found randomly at Uniqlo.
I would base this on how much you plan on wearing either pair of shoes. For instance, personally I rarely wear black shoes unless I need to really button down for clients or am involved in some other formal event/gathering. Thus, I would rather pay less for the black shoes and more for the loafers, as they’d get more wear. However, if the opposite is true for you, then I’d invest more in the work wear and less on the casual shoes. Don’t think you’ll be disappointed with either choice.
Another thing to think about is how much you value each style. I find black dress shoes to be pretty boring, so I wouldn’t spend a ton on them until I could afford a really elegant pair (“any captoe will do” is the basic mindset). I think Polo/Snuff suede is a great shade and goes with anything, and would thus be more likely to pay up.
-Well-fitted around the waist - drape maintained.
6x1 Not so good:
-Saggy, poorly-fitting, and archaic looking.
Much more difficult to pull off, especially for a younger guy.
6x2 - More leeway. The button stance allows for a better fit around the waist and a tighter silhouette.
Not sure where you can get a collar pin shirt currently, but there may be a few examples out there. You might have to go custom to get the exact fit you want.
As long as the collar points are tight enough, you can stick the right collar pin through any shirt - obviously you will leave small pin holes following wear though. Some guys like having the holes added before wear, but you may lose an element of the debonair with such uniformity. I think a little askewness is cool with a collar pin, as they are on the stuffy side to begin with.
Yay, but don’t go overboard. Keep the pattern simple and go for texture.