Q: I've seen other men wearing skirts on the internet, but you seem to take a different approach. Rather than working within accepted male fashion styles and bringing a skirt into the mix, you often wear completely feminine outfits. Since your style is already so close to a feminine appearance, why not go all the way (wig, makeup, ect) and present entirely as female?
A: Your observations about the differences in style and philosophy between myself and some other skirted male bloggers is true. I've actually talked about this in an early article on my blog, Boys in Dresses: A Primer. In the article, I talk about how I see a spectrum or range of opinions and styles among men who wear skirts (or other women's clothing). You can check out the article for all the details, but the basics of the theory are that on one end of the spectrum you have the "bravehearts", men who wear only kilts or other masculine skirted garments. The next step there, in my mind, would be folks like Mike at Fashion Freestyler, who often follow a "one item rule", wearing men's clothes save for one feminine garment, or otherwise do make an effort to maintain a masculine edge to their wardrobe. Down at the far other end of the spectrum, you've got full on androgynous fashion, the folks that either like to mix up gender presentation or outright defy it. While I don't present as androgynous or traditionally feminine, I do fall pretty far along on that end of the spectrum.
Muddy (har har) analogy aside, the answer as to why I don't just "go all the way" when I've already chosen to wear a dress, tights, and heels, is because I don't want to and don't feel that I have to. Ironically, despite the fact I'm a makeup artist by trade, I don't like to wear makeup. I don't wear a wig because I don't really like having hair (my baldness is, at present, completely by choice). I'm pretty content with being a dude, I just disagree with the social preconceptions that come along with my birth gender. In making the sartorial choices that I make, my hope is that it challenges some of those preconceived gender stereotypes that have been preordained and foisted upon us. The question of "Why is that man wearing a dress?" will hopefully lead to "What makes a dress for women only anyhow?"