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Does the alden leather get stinky after a while wearing sockless? My cavnas shoes I go sockless are smelly.
I never truly go sockless, but instead use "no show" loafer socks.
You should have each of those shell colors in each one of those models!
In all seriousness though, if you could only have one of each, I would go with the ravello LWB, cigar PTB, and the color 8 LHS. However, you could probably go with any combination with the options you've laid out and still be in great shape. I just happened to be a lover of the king of the gunboats...
The ravello LWB would be my first choice for my first Alden shell, but that's just me.