As a woman who owns many many pleated skirts (though not kilts), and wears skirts to work almost daily, I would not recommend anyone not wear briefs. The fullness added by the pleats is much more forgiving than a straight skirt.

My skirts range from just below the knee to just above - and even when I'm careful things happen. Walking up stairs, bending down to pick up a pen, leaning over in your chair all can put you in a position where more shows than you intended. If it's just your leg, or the edge of boxer briefs no big deal.

Regular boxers are going to give a view from the right... er... wrong angle. And though I personally would just laugh it off, the way work places are now a days, you would likely get a formal reprimand at best, or just flat out terminated for public exposure. Yes, even though they were looking.

I wear stockings to work - the real kind, with garters - so I'm very aware of where my skirt is sitting at all times and what shows when going up stairs, etc. The bottom edge of a stocking top seems to be an eye magnet (even though there is still another few inches to stocking before any leg.)

Just some thoughts...

Michelle