May 3, 2000

By Charles Anders

I'VE WANTED TO wear women's clothes for as long as I can remember. I was 12 or thereabouts when I took advantage of my parents' absence to try on a bunch of my mom's bras, slips, and panties. I took several photographs of myself in her ridiculously ill-fitting underwear, then burned the film before I could develop it.

Now I walk the streets, day or night, as "Julia." In the past year it's gone from being a scary secret to becoming a performance. And the most amazing part of it has been finding out how many guys want to do what I do. Men ask me for fashion tips all the time. One butch leather-punk told me he'd decided to go femme – "Let's face it, I've got great legs," he said.

The good news is, guys, it's never been easier to bring out your inner girl, whether she's shy or wild. And you can have a lot of fun doing it. You'll have to overcome your own social programming, a world that thinks gender is immutably assigned at birth, and a lot of so-called enlightened people's assumptions about what dressing like a girl means. (Wearing a skirt doesn't make you a drag queen, a transsexual, or a homosexual.)

But most of all, you'll have to figure out the mysteries of women's clothes. They lack the uniformity and simplicity of jeans and boxers. They weren't designed for your body type, most likely. (Actually, that's a problem many women have too.) And women's clothes are sold in places where you'll feel awfully strange showing your face.

Cross-dress for less

I started buying women's clothes three years ago, and it took me two of those years to understand the basics. Luckily, it doesn't need to take you that long.

Until last year I lived in Jesse Helms country, where I found only one tiny thrift store where I felt OK trying on women's clothes. It was an hour's drive from home. I would slink into the dressing room with a half dozen dresses that I was sure would fit me. None of them would. Once, I had to settle on a dress that I could get into but couldn't zip up all the way in back. I figured someone could help me zip it up later.

It turned out that dress wasn't going to zip up properly no matter how much help I got. This was mostly because of my ungirlish shoulders, a problem many men have. I didn't figure that out until I wore it to a party, where I stood with my back against the wall the entire time.

When I got to the Bay Area, I learned better. It takes time to figure out how to spot women's clothes that will fit a man's body. It also takes time to develop a personal style.

At a recent meeting of Transgender San Francisco (TGSF), I queried the girls about their wardrobe habits.

"You're going to build a brand-new person without any plans, and you're going to make a lot of missteps along the way," the fabulous Miss Didi Mau says. "A lot of the stuff you buy is going to be wrong."

Take Ally ("just like McBeal"). She originally wanted to be a Gap kid. Then a shopkeeper helped her realize the look that worked best for her was that of a lesbian feminist college professor, which, she says, "is pretty much what I am."

The problem isn't that people in most ordinary shops will laugh at you – although one gal did tell me of a large thrift store where the clerk liked to use the P.A. system to let shoppers know when a trannie was approaching the cash register, so everyone could go and see. Most stores want your money, so the staff behaves respectfully. But in the beginning, you may need more than just tolerance.

When I was new in the Bay Area, a friend took me to the notorious cross-dressers' shop Piedmont (1452 Haight, S.F. 415-864-8075) where the sales force took me under its collective wings and helped me pick out a fabulous outfit that I still wear. Unfortunately, it was really expensive, but it was my birthday. And the service was great. The staff brought me tons of clothes in the dressing room and were obviously used to dealing with scared fledgling transvestites.

I've had a lot of fun cross-dressing in public, including going swing dancing with a gal who dressed in a suit and wing tips. (She led; I followed; yuppies gawked.) And I was recently invited to attend a Republican fundraising dinner in a dress. My attitude is that I'll keep doing this as long as it's fun. But I can't have fun unless I'm comfortable, which is why I don't tuck my penis, wear odd padded girdles or corsets, or even sport a wig most of the time. I'm still figuring out what works for me, and you may decide a different approach works for you.

To choose a look, you should know what you're going for. Are you striving to pass as a woman, as most transsexuals are? In that case, go for the subtlest approach. Are you wanting to present an exaggerated version of femininity, like many drag queens? Then go all out with the big wigs and heavy makeup. Most cross-dressers I know seem to fall between those two styles of presentation.

Men's armpits, women's clothes

These days I mostly shop in thrift stores and low-end places like Ross Dress for Less, where the service is pretty nonexistent. But you may need some more help at first. So as a service to you, the would-be T.V.s of the Bay Area, I visited a selection of the city's finest clothing establishments. In each store I presented myself as a newbie transvestite in need of guidance.

Besides Piedmont, two other stores advertise in the TGSF newsletter, touting their eagerness to serve the newly "gender gifted": Foxy Lady (2644 Mission, S.F. 415-285-4980) and I Love It! (120 J. St., Fremont. 510-623-1357). Foxy Lady may be the store best known for serving trannies, but every gal I've ever talked to loathes the place. They complain of price gouging and rude service and praise the other two TGSF advertisers, I Love It! in particular.

I consider myself a seasoned old bitch now, but approaching a woman behind a counter and asking her to dress me like a girl still seems really humiliating and scary. The Foxy Lady salesperson, who gives her name as Kaga, isn't much help. She gives me a frosty look and asks, "Are you buying?" I say I might be, if I find stuff I like. Can she give me some advice? "What kind of clothes do you want?" I stammer and say I'm hoping to find something sexy. "The sexy clothes are over there," she says, gesturing at a rack.

When I ask Kaga if I can try some things on, she says only if I can guarantee I'm buying. After all, she says, other customers wouldn't want clothes that I have stretched out and left "smelly under the arms."

Suffice it to say, the rudeness charge has stuck. Nevertheless, the store's prices are comparable to Piedmont's, and it has a guest book crammed with praise.

Janine, the owner of Foxy Lady for 39 years, says that the rude treatment I received was "absolutely shocking" and that Kaga usually bends over backward to help customers, to the point where many T.V.s ask for her by name. On the other hand, she confirms that armpit issues have forced the store to return, dry-clean, or discard many outfits.

I Love It!'s owner, Jo-An, wears Winnie the Pooh slippers and a WWJD bracelet, and she obviously loves dressing men as women. Her eyes light up when I tell her my mission. "You've got the look," she tells me. But she's stern: she won't let me buy anything that doesn't fit, or a surfeit of "trashy" clothes that I can't wear to the mall.

Jo-An gives incredibly helpful advice on sizes and how to wear clothes, and after I try some things on for myself, she starts bringing other things to me in the dressing room. (She's very concerned that I might be nervous about trying on clothes with other customers in the store.) She's focused on helping me pick clothes that look good together but can be worn with a bunch of other things as well.

When I leave, she gives me her card and tells me to call her any time I have a question.

Next I go to Saks Fifth Avenue (384 Post, S.F. 415-986-4300) on Union Square. The salesperson there, Peter, spends a good 20 minutes with me and shows me a bunch of clothes. He's incredibly friendly and supportive, even as he lets me know that I'm in the Absolute Wrong Place and Should Leave Now. Saks is a "high-end" store, he explains, whose clothes require a "significant investment." Lest I buy an $800 skirt as a lark and then regret my decision, he also explains that Saks doesn't take returns once the price tag has been removed.

Peter suggests I stick to items that could double as men's clothes, presumably to maximize the return on my significant investment. Knit tops, slinky slacks, that sort of thing. "A lot of fellas" who dress up want to jump straight into skirts, Peter says, but slacks are a good start. "You're tall, of course. They're always tall," he says appraisingly.

I ask Peter if he gets many cross-dressers at Saks. He says no, but that he has one regular. "It's not really what we do, but hey – we're a clothing store," he says. Having shown me some price tags that approach my rent, he suggests I make my way immediately to the Gap. "You could even do Banana Republic," he adds as an afterthought.

My own executive personal shopper

Ask a sales assistant at Nordstrom (865 Market, S.F. 415-243-8500) or Macy's (Stockton and O'Farrell, S.F. 415-397-3333) for genderfuck guidance, and they'll direct you to a special part of the store where full-time helpers offer a complimentary clothes-picking service.

Nordstrom has "wardrobe consultants." The first two I make contact with pass me on, until I end up with Nicki, who's so new there that she has to scribble her name on someone else's business card.

Among the TGSF crowd, there's a pervasive myth that Nordstrom gives its staff a special "tranny training." When I ask the wardrobe consultants about this, they deny it, but they do say everyone's welcome at their store. One male consultant spreads his hands and says, "We help everybody," as if Nordstrom were the Red Cross. I ask him if T.G. customers are matched with consultants by "luck of the draw," and he replies, "Not exactly," without elaborating.

A Nordstrom P.R. person says, "Our salespeople receive diversity and sensitivity training on a periodic and ongoing basis," and that they are comfortable helping the clients wherever they choose to shop. "It really is just about the client's comfort level," she adds. She notes that many cross-dressers avail themselves of the personal shopper service because of the extra privacy and service: "Really, it is just about making the client feel the most comfortable. We're going to go ahead and accommodate them."

Nicki is incredibly supportive. We tour the store hunting for dresses I like. "What sort of look do you think would work on me?" I ask her. "Schoolgirl? Lesbian feminist college professor?" She just suggests we try on some random outfits. Nicki gets a 10 for validation but a 1 for meaningful feedback. Every outfit I try on looks great on me, at least from her perspective.

There are some to-die-for clothes at Nordstrom, including a green gown covered with iridescent green discs an inch wide. As I struggle into it, the green discs start falling off onto the floor and I glance nervously at the $300 price tag. I wonder exactly how many displaced discs mean that I've bought the dress.

At Macy's I have a session with an "executive personal shopper" named Lee. He tells me a close friend's partner was once the Empress of San Francisco, so he's got connections. Even before our appointment Lee pulls nearly 30 outfits in advance and researches addresses and phone numbers of other shops I could try.

Lee takes my femmy aspirations way more seriously than I ever have. He wants me to go get a padded girdle, corset, and padded bra so I'll have more feminine lines. When I think a dress looks good on me, Lee explains to me exactly why my nonexistent hips make it look awful. He's the opposite of Nicki at Nordstrom.

A Macy's P.R. rep says, "We don't have a specific policy [about trannies]. Everyone is welcome to shop here." She adds, "We have very expensive diversity training, and I assume it's covered in that." She hasn't taken the training herself, because it's only for sales associates.

Lee is convinced I shouldn't get serious about trying things on, much less buy anything, until I've got my foundation garments sorted out. "First you build the house, then you can come back and put shingles on it," he tells me at one point. (By contrast, Jo-An at I Love It! opposes lots of padding, saying I should be as "natural and comfortable" as possible.)

Don't get me wrong, I get tons of validation from Lee. When we finally part company, he tells me gallantly that I'll be "the belle of the ball." But if he'd been my mentor when I was starting out, I might have quit. Especially since his main recommendation for finding padded undergarments was the Foxy Lady.

So I've discovered that hatchling transvestites can get personal service at mainstream stores in the city. But what about in the burbs? To find out, I visit the Ann Taylor store in Walnut Creek (1189 Broadway Plaza, 925-937-0606), where the salespeople react cheerfully enough when I ask for help building a "classy, professional" look.

The smiles vanish, though, when I ask if I can try clothes on. "We're always kicking men out of the dressing rooms," one salesperson says. They go ask the manager if they can make an exception for me. Eventually, one of them comes back and says sheepishly that "we're not evolved enough here" to let men try on clothes. But the store does have a good return policy in case something doesn't fit. No thanks, I say. An Ann Taylor spokesperson later tells me that there is no company-wide policy on dressing rooms.

Stroking in the boys' room

My first month in the Bay Area I found a gorgeous silvery dress at a thrift store. It fit perfectly and even zipped up in back. I wanted to go clubbing, but I was scared to wear it on BART, and moreover I didn't know how to do my own makeup. So I put the dress on in the men's room at the club, and my date did my makeup in there. Eventually the men waiting to pee got so insistent that we let them in, and she brushed on my mascara while men urinated inches away.

I had a wig with me, a $20 Day-Glo pink monstrosity that resembled the troll dolls that were big when I was in junior high. My date flushed it down the toilet in disgust.

So I realized I needed to learn to do my own makeup. And I needed to get a better wig, or not wear one at all. (If you have male pattern baldness, the latter may not seem like an option.) The makeup I mastered with the help of the staff at Kryolan (132 Ninth St., S.F. 415-863-9684), a theatrical supply store on Ninth Street that caters heavily to gender upstarts of all stripes. I got a wig at Piedmont, although I've heard good things about a few wig stores in town. Be prepared to spend a decent amount of money on a wig and get one with the appearance of a real scalp underneath.

As for riding BART en femme, it took months before that stopped terrifying me. Once, I put a fetishy latex dress on, then threw street clothes on over it on a hot day. The outfit got sweaty and rumpled, and I looked so odd that people stared at me more than if I'd just been wearing the outfit uncovered.

It's hard to believe how bold I've gotten since then. I even came out to my parents as a cross-dresser recently. (I didn't mention that I tried on my mom's things when I was 12.) My dad didn't react much, but my mom got really interested in it, and we even went shopping together.

Then, when I was getting ready to return to San Francisco, my mom took me aside and asked if I'd do something for her. She had an outfit that she'd bought when I was five, a skirt, sweater, and top combo that didn't fit her anymore. It had great personal significance to her, and she wanted to know if I'd wear it for her. I wear it with pride.