These, and your Cigar Captoe boots on the Plaza are my favorites of yours.
Here's my almost 2 years old Cigar Indys with some hairy RRL Raw Low-Straight denim
I like this a lot. Especially the CXL leather. I have a brown CXL Wolverine 1K oxford shoe and I'm loving the patina that develop every time I wear it. It is hard to decide... I'm not sure it is a wrong thing to check out this thread because I got addicted to the shell material and it is soooo cool.
Welcome to the forum. This is indeed a great place to learn from the pros in a gentlemanlike environment.
My first Alden purchase (a little over a year ago) was the Alden shell Color 8 Chukka. While I love them, I find that the eyelets are not enough to keep my foot firmly fastened within the shoe. That has not stopped me from wearing them weekly, but next time I will go for a six eyelet chukka. If I had to do it over again, I would have definitely gone with the No 8 PTB.
Good luck and enjoy your visit to NYC.