Kilts in the office

[Archangel]

I think I'm beginning to see what you're after. You're a senior employee and are expected to set an example to the juniors. I've been hit with that too. It surprised me that I had gained that much seniority. It surprised management that I was not that impressed and not willing to take on the responsibility of being a good example.

Here's what I see. You really want to do this and do it as perfect as can be. Realize that perfection is not attainable. Close will have to do. You're also trying to determine the kilted equivalent of the business uniform. I'm not sure it translates well but your best bet would be to wander around 21stCentury's site: http://www.21stcenturykilts.co.uk/discountedpackage.htm. The kilt doesn't translate well. I prefer to think of it the other way around. The business suit is wrong. Anyway, if you are trying to find the right jacket to complete the look, I would suggest you give up, for now.

My personal rule is when in doubt, try and look military. I would suggest khaki colour shirts with military type pockets, Eddie Bauer usually has this style. Hamish would suggest socks to match. In an office I would suggest the thinner socks rather than the thick wool ones, heavier shoes rather than boots. A thin black tie would complete the look, a tie with a small clan crest would help keep the focus. These aren't any rules, they're just what I'd try to do.

Anyway, at some point you're going to have to jump out the plane.
Here's the samurai philosophy, which works well in this kind of case: prepare to die. This means as you approach the situation what is the worst that can happen? Can you accept that? If yes, go: if no, stop.

My feeling is that you would be okay. You're a senior employee, you've got some kind of permission, there is a HR department. You might get called in to discuss this. You've already got lots of advice from here so you know the parameters, make them chase you, give them short, one word answers. Worst case scenario, they tell you not to do it again. That starts you off on another campaign. Each step has a specific response.

Do you have casual Fridays, United Way Fridays, gosh, why not? That would be the best way for you to test the water.
Or dive right into the deep end Monday morning.
Either way, you'll just add to your legend.

Best wishes.