The Mysterious Disappearance of Chicago’s Policewomen: Once Seen in Skirts, Now All Gone Without a Trace!

Once upon a time, Chicago had policewomen—real, skirt-wearing, gun-carrying women of the law. They weren’t the hardened patrol types, but they were there when needed. Their duties were almost always centered around dealing with women prisoners, abandoned children, or the offspring of arrested adults. The policewomen were corralled into the Youth Division, dealing with runaways and abused or delinquent kids. And yes, they were protected—zealously so. You wouldn’t catch one out on a midnight beat or in a dangerous situation. They had the same training and powers as their male counterparts and carried guns, but danger? Not on their watch.

Back then, the sight of a policewoman was as rare as a unicorn. In the 1960s and early ’70s, there were just 90 policewomen in a force of 14,000 men. Adding to the confusion were the “matrons”—female officers limited to tending women in lockups, sworn in but barred from carrying firearms. Their stylish uniforms, reminiscent of airline stewardesses, were adorned with the police star and patches, just enough to set them apart.

Gunfights? Almost unheard of. Only two stories stand out: One, a policewoman, Helen Dewitt caught a bullet in the calf while riding in a marked car around 1970, and the other—a legendary case—where one policewoman fired her service revolver at her detective husband. He was so terrified, he quit the department and moved to Las Vegas eventually became a celebrated screenwriter. The department, however, shrugged off the incident without disciplinary action.

It was a cushy gig—safe, secure, and decently paid. With only 90 positions available, job openings were rare, and competition was fierce. The most recent policewoman’s civil service exam saw 7,000 hopefuls vying for 30 positions that would open in the next decade. Naturally, those who made the cut were bright, better educated, and resourceful—intellectually a cut above many of their male colleagues. They were fast typists, sharp writers, and typically had their wits about them.

Then came the lawsuits. Equality was demanded. In the mid-1970s, the grand experiment began—integrating women into field patrols alongside men. Some women proved braver than their male counterparts, while others…not so much. But one thing was clear: their sharp minds often de-escalated situations where testosterone failed.

Soon after, the department gave policewomen the option to ditch their skirts and take on the title of “patrolman” (because “patrolwoman” wasn’t a thing yet). Most jumped at the opportunity, especially since it meant they could climb the ranks to sergeant, lieutenant, and beyond. From that point on, new academy classes were fully integrated, and women competed alongside men. However, as standards dropped to meet diversity and inclusion goals, gone were the intellectually superior, well-educated policewomen of the past.

Federal Judge Prentice Marshall’s ruling on civil service testing threw white males out of contention for appointments or promotions, ushering in a new era. The matron ranks also vanished, as they too were folded into the patrol division—despite never having fired a gun before. Many didn’t even own one! But training soon followed, and the matron role became a thing of the past.

Today, the department is a fully integrated mix of men, women, and now even transgender officers patrolling Chicago’s streets. As for those original policewomen? They faded away, one by one, through retirement and attrition, leaving behind only their stories and a few fleeting memories.

Oh, and in the end, four female Chicago police officers have lost their lives in the line of duty: Dorelle C. Brandon (1984), Irma Ruiz (1988), Ella Grace French (2021), and Areanah M. Preston (2023). But those brave souls were far from the skirted policewomen of old—they were the new breed, forged in the modern, integrated force. The skirts? Long gone.

Personally, I miss seeing some of the prettier Policewomen in those little pencil skirts and high heels.