At the annual Halloween costume contest in St. Louis’ Central West End, all the Halloween staples are present. There are superheroes, vampires and men in dresses.

One man wearing a little red dress for the night’s festivities was Ron Reed. He dressed as Strawberry Shortcake -- high heels, green and white striped thigh high hose and a wig are all included in the ensemble.

Reed says he likes the attention he gets in the outfit.

“I just like being able to go out on Halloween and being able to be free and showing off. It’s just about being free,” he said. “The attention I get from women is incredible. The attention I get from everybody is incredible.”

Reed’s outfit went over well with the crowd as he took the stage for the costume contest. It’s a look that might not have received such positive reviews 30 years ago.

According to attorney Arlene Zarembka it’s a costume that then could have resulted in Reed’s arrest.

St. Louis adopted an ordinance prohibiting cross-dressing in 1864. The so-called masquerading ordinance made it illegal for any person to appear in any public place in dress not belonging to his or her sex. The law also made lewd and indecent dress and conduct illegal.

The ordinance stayed on the books until 1986, when two of Zarembka's clients filed motions to have charges of cross-dressing and indecent and lewd conduct dismissed.

The case resulted in a revised law, which no longer prohibits cross dressing and redefined indecent and lewd acts.

Zarembka says, although she can only speculate what the initial purpose of the ordinance was, its meaning shifted with time and was sometimes used in the later half of the 20th century to target the LGBT community.

“Because it was on the books and it had been on the books since the 19th century, the police could use this to harass gays and lesbians as they were starting to come out of the closet and become more visible,” she said. “Gays and lesbians who were visible were always subject to arrest.”

A Halloween Arrest

The masquerading ordinance was used to arrest Greg Smith on Halloween in 1969.

“I had on a purple dress -- it kind of looked like a Chita Rivera-West Side Story dress with these little kind of ruffles on it -- and a blonde gold wig done up with banana curls,” Smith said.

The 20 year old was also wearing his mother’s diamond earrings.

Smith was with a group of gay men (see the video below). Although many of them had never cross-dressed before, some of the group decided to celebrate Halloween dressed as women. The group went to Olive Street, where a handful of gay bars and coffee shops were located.

“So were all having this really good time at the Onyx Room,” Smith said. “I think we were walking down to the Golden Gate coffee house and then all of the sudden the police came up. They grabbed about 6, 7 or 8 of us, who were all dressed as females and put us all in the back of a paddy wagon and took us down to the main police station on Clark Street.”

At first Smith didn’t take the arrest seriously.

“They fingerprint us and put us in jail; and I’m in my cell with my friend Michael. And so Michael and I are singing and dancing ‘Let me entertain you, let me make you smile’ from Gypsy; and then all of the sudden this police officer comes over and you could tell we were in more trouble than we thought we were in,” Smith said.

Smith called his parents to come and bail him out of jail. Although they weren't happy, they agreed to come and pick him up.

“So I get to the processing desk to leave and the guy says to me I want you to take that wig off and walk out of here like a man,” Smith said. I said, ‘I don't think so.’ I’m in a purple dress and gold heels. I said, ‘I’m going to walk out the way I came in.’ And there was like this swinging door, and I swung it open and there were my parents on the other side of that door.”

Emanuele Berry|St. Louis Public Radio

Besides his angry parents, a crowd of supportive protesters mobilized by the Mandrake Society greeted Greg when he left jail.

“It was so heartwarming to see all these people there to support us,” Smith said.

But his presence in the welcoming crowd was short lived.

“My mother and father are really upset at this point. Out of the police station they’re behind me, chasing me get into the car. My mother looked and she saw the diamond earrings and she grabbed them off my ears,” he said.

Mandrake History

The Mandrake Society was one of St. Louis first LGBT organizations. Steven Brawley of the St. Louis LGBT History Project says the group had just started to take shape in the months prior to Halloween.

“We don't know a lot about those early months,” Brawley said. “We know that it was a group of folks who came together, and it wasn't really until the Halloween arrest that they sprung into action and got on the radar.”

After learning of the arrest, the Mandrake Society gathered protesters at the police station, raised bail money and hired a lawyer to challenge the charges made against the men.

A few months later, a lawyer appointed by the Mandrake Society defended the men.

“The lawyer argued that all the men who dressed up for the V.P. Fair Parade and all the men dressed as Santa Claus should also be arrested under the masquerading law,” Smith said.

The charges were dropped.

The Mandrake Society eventually published an LGBT publication called Mandrake and held an annual Halloween Ball, which included the crowning of a Miss Mandrake and a masquerade dance.

Brawley says Halloween 1969 was a pivotal time for the LGBT community.

“This case provides this foundation that we now call St. Louis’ Stonewall, where before everything was sort of quiet and there were bars and there was life, but there wasn't this organized effort,” he said.