Charles Anders is a fixture on the San Francisco queer writing scene, writing erotica (check out the recent anthologies Tough Guys and Best Bisexual Erotica 2), as well as journalism, about transgender and crossdressing issues. Now this 30-year-old writer has released The Lazy Crossdresser, an advice book on how to crossdress with relative ease.

I met Charles through some friends last year, and having heard about his crossdressing tendencies, honestly wasn't sure what to expect, but upon meeting him found that his crossdressing pretty much blended in with his personality. Whether wearing a camouflage skirt at a San Francisco café or a more elaborate outfit to a reading or party, Charles manages to seamlessly blend his crossdressing into his life. In fact, he does so well as a woman that he recently won more than $1,000 on the game show To Tell The Truth!

The Lazy Crossdresser offers humorous as well as informative advice about how to wear women's clothes without agony. The book delves into reasons why men crossdress, ways to go about it, and most of all, how to feel comfortable doing it. As Virginia Postrel writes in a recent issue of Reason, on the subject of Afghani women and their newfound freedom to wear nail polish, "By reshaping or decorating our outer selves, we express our inner sense of self: I like that becomes I'm like that." For Charles, crossdressing is not just a way of adorning himself, but a way of defining who he is and enjoying (and owning) his body.

I spoke with Charles recently about a host of issues, including his own crossdressing, his female alter ego Julia, advice for others who want to or already do crossdress, and some of the gender issues brought up by it. (And for the record, though he sometimes uses "Julia" to describe himself, I consider him "Charles" no matter what he's wearing; to me, it just fits, whether he's in pants, skirts, or any other combination.)

CS: You write that you started crossdressing, or wearing women's clothes, at a very early age. Do you feel that it was genetic or natural to you?

CA: I don't really know. It's something that I was always interested in and always thought was really cool. It was just something that fascinated me in my early teens, and then I kind of left it alone for a long time, and then I came back to it more recently.

CS: How early is your first memory of being interested in it?

CA: I don't know, I guess I was curious about stuff like that when I was a little kid, but the first time I actually tried it I was maybe 14. I'm not sure exactly how old I was, but I was definitely in my early teens.

CS: Why did you write the book?

CA: Because I felt like there was no book out there for crossdressers that really walked them through it in a friendly way and made it less threatening and mysterious to them. There are people out there who feel like they have the right way of doing it, and anybody who doesn't do it their way is bad and wrong. I guess part of what makes crossdressing special is that there's a lot of guilt around it, and a lot of people who crossdress feel as though they're bad people for wanting to do it. And when people worry about doing it wrong, or that they're too fat, or that they're too something else to be a good crossdresser, that totally plays into the sense of guilt, because it's easy to get from "I shouldn't be doing this because I'm a guy and guys don't wear women's clothes" to "I shouldn't be doing this because I have the wrong body type or I'm not doing my makeup well enough or because I'm not doing X, Y, or Z well enough." And it's the same thing; it's the feeling of inadequacy and the feeling of doing something wrong. It's hard to separate the guilt from the feeling of not being able to do it without killing yourself, and so I'm kind of trying to chip away at both things -- the guilt and the feeling that unless you're willing to work your butt off and make yourself miserable you can't do this. I think people punish themselves. One of the reasons why people make it so hard for themselves is that they're punishing themselves for wanting to do this in the first place.

CS: What are the other books out there like?

CA: There was no book out there like this one. I really wanted to demystify it and make it less scary for people. There are people who can explain it but not necessarily demystify it, and I wanted to do that, and make it more like what regular women do. The women I know experiment with different things and have fun with it and don't obsess about being perfect all the time, especially when they're just wearing women's clothes day to day. Most women aren't that freaked out about it.

CS: Is the book only aimed at men wanting to wear women's clothes?

CA: No. I've been told by a lot of people who've looked at the book that genetic women would be interested in reading it, and I'm really hoping that'll happen. I'm hoping that there's a lot of crossover and that genetic women will pick it up and start reading it because it's actually something that women might find really useful.

CS: A lot of the book is focused on how to dress and where to shop and questions about clothes and makeup and things. How much of it for you is about material things, and how much of it is something else?

CA: What do you mean by "something else?"

CS: I guess something that you don't need to buy, something more personal -- does that make sense? My question is how do you place yourself, your own vision of what you want to be when you dress as a woman, into the process?

CA: Where the process begins for me is trying to come up with an image, and that may be not the same image every day. For most people, they come up with an image at the beginning of the process in general, but that can change day to day. It's all about choosing an image of yourself that you're comfortable with, and then picking clothes and stuff to go with it.

CS: That's kind of what I was asking about, can you elaborate about that?

CA: Some of it is internal; it's not all about buying things and objects and stuff, but the objects -- the clothing, jewelry, and makeup -- are how you express something internal to yourself in a lot of cases. It really depends on the person and what they're trying to get out of it.

CS: You write about your female alter ego Julia. Do you actually go by Julia?

CA: Sometimes I go by Julia, but most days I just don't make a big deal of it. Like I say in the book, I don't really see a huge distinction; I'm the same person no matter what I'm wearing, so it's not a big deal.

CS: Is that a new or different idea than is usually held about crossdressers? It seems like one of your points is that that's pretty different than what's been said before, that for most people it is a big shift.

CA: I hate to generalize because every crossdresser is different and it just depends on the person. For some people it's a huge difference; when they get dressed up they feel they've become a totally different person. I think that most people I've talked to have found over time that when they crossdress on a more regular basis, it becomes more natural and becomes more a part of them. It's less like there's this other person that they become, which is kind of schizophrenic and artificial. It's more like how some people dress differently on the weekends or dress differently in the evenings than they do during the day when they go to work. Wearing women's clothes versus wearing men's clothes is just a different way to dress and express themselves.

These days, pretty much all the time, I'll answer to either Julia or Charles. People who've known me for a while as Charles can always call me Charles because I'm not going to give people a hard time. I don't think it's really fair when I'm going back and forth all the time for me to give people a hard time over what they call me. I'm pretty much always happy to be called Julia.

CS: If you feel like the same person, like you have integrated the two (Charles and Julia), then how does Julia differ from Charles?

CA: I don't even know that there's that much difference anymore. I think they've pretty much become the same person.

CS: Has that shifted? Was there a time when they were a lot more different for you?

CA: When I was first dressing, I felt like this was a totally different side of myself, and now I just feel like it's part of who I am.

CS: How often would you say you go out wearing women's clothes or makeup?

CA: Pretty much every day.

CS: In your daily life?

CA: Yes. Every now and then I have a day when I just feel like wearing androgynous clothes, but I crossdress almost every day in public now. It's pretty much who I am. In a lot of ways, I have a lot more in common with some transsexuals I know, because I'm crossdressing on a daily basis, and that's who I'm presenting -- a more female persona to the world. I've become a lot more female-identified lately, but I'm not particularly inclined to actually change my name legally or start hormones or anything like that. I'm just happy to wear women's clothes.

CS: Do you consider yourself transgendered?

CA: Yes, totally. I think any man who wears women's clothes, even once in a while, is transgendered, anybody who starts to cross that line.

CS: Can you elaborate on that? Because I was going to ask you about how the act of crossdressing interacts with the notion of a binary gender system, how it either conforms to that or doesn't. I think you can see it on both sides; it depends on what the reasoning is. I think that if we think of it as crossdressing, as wearing the opposite gender's clothes, and becoming an opposite person, that can play into that, but if it's something else, then it could kind of work against a binary gender system.

CA: I talk about that in the book; I talk about how a lot of crossdressers I know feel as though they're bigendered, or ambigendered or somewhere in between. And in fact they feel as though they have a fluid gender identity; they can go back and forth, or they can be somewhere in the middle. Most people I've talked to feel as though they're somewhere in the middle most of the time. But it's less of a rigid distinction than it used to be. Certainly this is one area where men have lagged behind women, because women for decades now have been able to dress more male or more female depending on their mood, and it's something that men have been restricted from doing, so it's more just men catching up with women.

CS: The point you make with the book is that people don't need to look exactly like a woman if they're a genetic man in order to crossdress. Could you elaborate on what you mean by "lazy crossdressing" -- what does that mean to you, and why did you call it "lazy?"

CA: To a lot of people crossdressing is inherently really hard work, and they have this idea in their minds that beauty equals pain and beauty equals hard work and that it's like a full-time job. If you're a man trying to look beautiful, then you're just going to have to suffer and toil in order to accomplish that. And people get kind of neurotic about it; women as well as men have this issue. And feminists have worked hard to divorce beauty from toil, and also from this one-sided standard where you're only beautiful if you conform to a particular image. What I'm really doing is saying that there's more than one way to be beautiful, and that there are ways to be beautiful that are nearly effortless. If you enjoy it and if you're doing this because you're having fun and you're doing this for the love, then it's not work and, in a sense, you are being "lazy." I'm not saying that everybody should just do absolutely no effort whatsoever and not try to look beautiful at all. I think the point for most people who crossdress is to look beautiful, but I'm saying that you can look beautiful without making yourself miserable. That's what women have had to confront over the last 50 years, disconnecting beauty from misery. Most men get away from this by just trying not to be beautiful; most men assume that they're never going to be beautiful anyway. Men who want to be beautiful assume that it takes a certain amount of suffering and hard work, and I'm trying to help them get away from that.

CS: That's really interesting, especially your feminist analysis. Are there crossdressing communities and support groups out there for people?

CA: There's actually a lot out there now, and not just here in San Francisco, but in Iowa and Arizona. In places where you might consider it kind of conservative, there's a lot of crossdressing support groups. You mentioned Veronica Vera earlier [ed. note: before this interview started]; there are now schools like hers pretty much in every major city in the country, and those are listed in the resource section of my book. There's one that I heard from recently in Austin, Texas that I barely got listed in the book at the last minute. Almost every major city has one of those.

There are thrift stores that quietly specialize in helping transgendered people. Apart from resources like my book and the Internet, you can get plugged into a local support system almost anywhere in the country, and they'll help you to find all the other stuff you need, like if you want to get electrolysis. Which is very painful -- I just had some electrolysis this afternoon and it hurt like hell. But if you want to get electrolysis or go clothes shopping, they'll tell you where the best places are. That's all in the resource section of my book, and I'll hopefully keep updating that on my Web site as well.

CS: Are the people involved with these groups both gay and straight?

CA: It really depends. There are some groups for crossdressers which stipulate that their members must be heterosexual. And actually I'm not sure how you define heterosexual in this context, because if you're dressed as a woman and you're interested in women, in some senses that would make you a lesbian. But I guess to their minds, they're still men, even though they're wearing women's clothes and going by women's names. A lot of them are married. There is a national network of support groups that insists that its members must be heterosexual. I think most any group that will welcome queer people will welcome straight people as well. I've never come across a queer-only transgender support group. There are plenty which are inclusive of everybody. Most crossdressers are straight, straight meaning that they like women exclusively; at least that's what I've always heard, but I've never seen meaningful statistics.

CS: I think that's really interesting. That goes back to the question that I asked you earlier about whether you consider yourself transgendered. I'm not saying that you can't be straight and crossdress, but I think there's definitely an element of fucking with what it means to be a man if you're wearing women's clothes. That doesn't negate you wanting to sleep with women, but I think it definitely questions the gender roles that we have. They might not want to question them in the same way as you or I do, but it's an interesting issue.

CA: There are some people for whom it's definitely not an act of rebellion or an act of challenging the status quo; it's just something that they really enjoy. And I think that's great. It's just something they feel the desire to do because they want to explore a different side of themselves. It depends on the person.

CS: You wrote in the relationships section, "I have a wonderful partner who calls me Princess, takes me clothes shopping, and delights in my appearance. I've never felt as beautiful as when she admires me, and because I feel so comfortable being a girl with her, I can see the beauty in her and cherish her more as well." And I'd just read this essay that your partner Annalee Newitz wrote at Nerve called "Trannychaser," and I really liked that because you two seem really made for each other, and you also seem really cute together. So I want to know, how can a crossdresser, lazy or otherwise, go about meeting someone compatible? That also seems to be an issue; even if you can be comfortable with yourself and crossdress in the way that you want to, but then finding someone who can accept that person that you are is something else that might be more difficult.

CA: Again, it depends what you're looking for. It depends on whether you identify as gay or straight or bi, to some extent, but not entirely. I talk about this a lot in the book; if you're already in a relationship or married, it's a whole question of coming out to the person in a way that doesn't scare them off and that lets them know that this doesn't necessarily mean that you're going to be a different person or that you're going to be unfaithful to them in any sexual sense.

As far as finding a partner, if you're not in a relationship or if you're non-monogamous, I think it's important to be honest about that part of yourself from the beginning. Obviously the easiest thing is if you're like me, and you feel comfortable going out in women's clothes and going to parties or clubs or events dressed up, then everyone you meet will know about that, and they'll either be comfortable with it or not; it's up to them. If you're not comfortable with that, then you either have to date people and let them know early on in the relationship, or you can put up personal ads saying that you're a crossdresser. If you're looking for an actual relationship, try to steer away from people who are just looking for casual sex and who are just curious about your crossdressing. One of the things I talk about in the book is trying to make yourself seem a well-rounded, genuine person in addition to the crossdressing. Don't just say "I'm a crossdresser and I'm looking for a partner," say "I'm a crossdresser and I like the poems of Emily Dickinson and I like to watch baseball and I like to go skiing," or whatever. Tell more about yourself. Find someone who can respect you as a well-rounded person as well as as a crossdresser.

CS: You said earlier that you crossdress pretty much every day. What kinds of reactions, positive or negative, do you get from both people you know and from strangers?

CA: Mostly it's pretty cool, and I don't think that's just San Francisco. I've crossdressed in other cities now, and usually if people can't tell what gender you are, they'll just give you the benefit of the doubt.

CS: In other words, assume that you're a woman?

CA: Yes, or reserve judgment. On the street, I sometimes get people making remarks, and I've been harassed occasionally.

CS: In San Francisco?

CA: In San Francisco, yes. I didn't have any trouble when I was in Atlanta or London dressing up, perhaps because people were less used to seeing transgender people, so they didn't think about it. Generally it was pretty mellow. I blend in, I look comfortable in women's clothes because I wear them a lot in public, and I try not to wear a really flamboyant outfit unless I'm going to an event where that's required. I guess I feel like it's possible to tone it down and still look glamorous, and gaudy isn't necessarily the most glamorous thing.

I think a big thing about going out in women's clothes is having your own comfort level, and feeling comfortable enough in them that you can walk down the street and not worry what people are going to say about you. I think one of the biggest problems is when people can sense that you're nervous or that you're afraid of being caught out; they tend to pick up on stuff like that. It's one of those things that I encourage people to do -- if you're going to go out dressed, work up to it and establish your comfort level over time. Definitely don't go out in an eye-catching outfit your first day, because you will get a lot of attention; work within your own zone of comfort.

CS: What's your favorite outfit to get dressed up in?

CA: I don't really have one favorite outfit.

CS: What's one of the most extravagant, or one that you put the most effort into?

CA: I used to have a great Wonder Woman costume that was really fun. I have some gorgeous dresses my mom gave me that used to belong to her, including one that my grandma made for her in the early ‘70s. It's really beautiful and has all this lace and all these layers of lace and floral linen. And I have this gorgeous red dress that I got recently from a drag queen that's really tight and long and flowing, and has a slit up the side. I wore that this past weekend and it went over really well.

CS: The first time someone mentioned you to me, they described you as "a slip of a girl/boy," and then I met you and I thought, "Wow, that's pretty accurate." How would you describe yourself in terms of your identity -- do you identify as a girl, boy, crossdresser? How do you think of yourself?

CA: I kind of think of myself as a girl, but I'm not attached to either identity; I'm somewhere in between. I guess I don't think of myself as a boy anymore. I've been female identified or wearing women's clothes for long enough that I've stopped thinking of myself as a Boy with a capital B. I'm either a girly boy or I'm a tranny girl or something, I don't know.

CS: Do you even think of yourself as any of those, or just as Charles?

CA: I guess I think of myself as Charles and/or Julia. Mostly I think of myself as Charles. I have a hard time letting go of the name Charles, because that's what I was born and what I'm used to. Especially since some people think Julia's kind of a silly name for me. I have a hard time letting go of Charles -- I need to come up with a new woman's name or do something. I resist categorization these days.

CS: Do you have any final words of advice for Clean Sheets readers?

CA: Beauty may not always be effortless, but it shouldn't be joyless.