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