What is the least offensive way for a dude to wear a skirt?

I actually said that this morning.

One of my favorite networking events is today. The list of things that are awesome about it runs really long, but perhaps the best part about it is the facilitator. She's just one of those fabulous, heartfelt people. Which is why the group has been meeting regularly for 14 years now.

So what's the problem? Probably just me. The event is held at a country club. I called before the first one I attended last fall just to find out what the dress code was for men, and the only requirement mentioned was a shirt with a collar. For women the dress code is pretty relaxed, and frankly, I haven't seen the dress code be upheld strictly for either gender. But what's the dress code going to look like for a dude in a skirt? Originally, I was going to wear my bright pink t-shirt with 30DaysinaSkirt.com printed on it, because it tends to generate conversation rather than conflict. And just explaining what I'm doing before they confront me on dress code seems like it might give the opportunity for some grace.

Flip-flops are probably not dress code compliant, either.

After much debate with my spouse, I went with my usual Hawaiian shirt. Standard networking garb on my part. It has a collar, is considered dressy enough for most settings, feels authentically fun to me, and frankly, is memorable, which is key to networking.

But I'm still sitting here scared of the dress code.

Its hard not to see an intersection with class here. I'm automatically out of place in country clubs, even in my nicest suit. My parents were public school teachers and church employees while I was growing up, so we just didn't ever see the inside of a country club. I've visited clubs as an adult, but again, I know that a lot of what has been in play has been my own privilege. I can pass as a Great White Male.

The skirt kind of wrecks that myth. One of the best things about it, actually.

I work with clients all the time as they prepare for big events, and one thing that comes up often is how to dress. The question I ask is "What supports you in feeling confident?" Or if not confident, whatever state of being they want to embody. The problem is...feeling confident in a skirt just doesn't work for me. While it feels incredibly comfortable, it also feels very vulnerable. Feeling confident while wearing a skirt is an act of sheer will on my part, in spite of my clothing.

Maybe this is yet another time I'm going to be surprised at the generous, curious nature of others. Feeling hopeful...

but not confident...