So here's where I am (more specifically):
- AE park/fifth ave (I like the punch cap better personally and don't think it will matter given how few truly conservative scenarios I am in)
- Alden Men's NST Tie Shell Cordovan Aberdeen Last (#8)
- Monk Strap
- Possibly a merlot Oxford of some sort (probably a wingtip)
This has been really helpful- by no means does it need to stop because I'm enjoying the comments, but I think I have what I need to begin. Thanks!