I won a trip to Cancun at work. I was elated as one of the few in my company who would enjoy the all-expense paid trip for myself and my wife.

I called up my parents, and my dad (who very strongly disapproves the kilt) remarked, "I wouldn't wear that skirt down there if I was you." I ended the conversation soon thereafter.

At work, a fellow employee who I don't actually know that well told me he wouldn't wear the kilt to Mexico, arguing, "When in Rome, do as the Romans." I gave a remark of, "I don't have a Toga" to the unsolicited advice. I've not worn pants since December 28, 2003

Still, I had some anxiety about it, particularly as I'd be meeting our COO at an event that was labeled business casual but "you're free to dress up."

Of course that was my "loophole" for the kilt which didn't make the list of men wearing khakis. With some extra cash, I decided it was time to buy some new kilt stuff, I'd been wanting. I got a steel on a Kilt Jacket (Montrose doublet) along with a new sporran. (Goat Hair with a Flag of Scotland pattern.), Kilt Belt with Buckle, and Kilt Pin in the family crest. I picked all this stuff up for under $250. (Ebay is your friend.)

Well, I didn't wear this around the resort. I wore my family tartan kilt, as well as my Royal Stewart Bear Kilt. I went to Chichen Itza and one of the guards there asked whether I was Scottish. I was asked a few times by curious hotel staff whether I was Scottish or English, but other than that in Mexico I got 0 reaction.

Now, its true Cancun is a big tourist area and you might not get away with as much other places, but still it went very well. As I was near the beach, I brought along a denim jacket that I wrapped around the rear of the kilt to keep it from flying up and I had very little problem in that regards.

I walked down when my turn in line came. I could tell he was surprised. He then said, "I like it." I said, "Thank you." I shook his hand and then walked down the aisle, I walked back down to the end of the convention room, shook hands with another group of company executives, another one of which complimented me on my kilt.

So everything worked out wonderfully despite my nervousness and the attempts of others to make me nervous.