Oh no the Darkside looms!

[DocHolliday]

If you're going for khakis, what about something a little more rustic? Maybe Orvis Rhinohides? Or do you think that would be too casual? I actually think they look better than most khakis.

Just trying to offer ideas that fit with what I've seen of your normal style.

 

[Crane's]

Doc, I have some of these around the house along with other Filson pants. They are a step above jeans for sure. The pants from BB are a little more refined though. I'm sure when this is all said and done I'll end up with clothing that will fit every occasion I find myself in. I guess my approach is along the lines of continuing where I left off and moving up from there. God only knows I would go into cardiac arrest if I had to wear a bespoke suit tomorrow. Oh and RL is around the corner from BB so I'll have to take a look at those shirts that were suggested.

 

[SkinnyGoomba]

Maybe some badass shell cordovan double soles for the shoes.

 

[Crane's]

Cordovan would be nice but nothing I've looked at has a cleated sole. The AEs in my OP do have a cleated sole and would do nicely. Part of the problem with what I'm going to be doing is discretion. To maintain the element of surprise one must not give any appearance that would be a tip off to a threat.

 

[AlanC]

Maybe something like this (calf):

Or (shell):

 

[Crane's]

Nice Alan, very nice. Now I really need to save the peanuts.