One lark the teens of yesteryear would occasional indulge in was cross-dressing for fun. While usually reserved for Halloween and other parties, that wasn’t always the case.

Click an image to open it in Flickr. Many persons in the pictures are identified.

1904 - cross-dressing leap year party - Enquirer - 25 Feb 1904
Bremen Enquirer – 25 Feb 1904

Friends of the Kuntz/Koontz boys, having switched outer clothing.

1911 - Young people having switched coats and hats
Koontz Family Collection – October 1, 1911

Just the boys…

1911 - Young men dressed as gals
Koontz Family Collection – October 1, 1911

The Sensow family were LaPorte relatives of the Kuntzes.

Calvin Koontz collection - 35
Koontz Family Collection – 1912 or so

Another shot, in the original color.

Calvin Koontz collection - 34
Koontz Family Collection – 1912 or so

Unknown girl dressed as boy in Hans-Nufer Family Collection.

1922 or so - cross-dressing girl
Hans-Nufer Family Collection – 1922 or so

The same girl with two boys dressed as girls.

1922 or so - cross-dressing teens
Hans-Nufer Family Collection – 1922 or so

Of course, it wasn’t always a lark. The art of “female impersonation” was a respected comedy device, as when a well-known Hoosier actor came to town to stage a performance with the help of local talent. Alas, no photographs of Vonna FitzGerald in male or female attire seem to have survived.

Vonna FitzGerald - Enquirer - Mar 4, 1898
Bremen Enquirer – 4 Mar 1898

But the newspaper man sometimes cast a queer eye on such shenanigans….

1891 - girls dress as negro tramps - Enquirer - 20 Nov 1891
Bremen Enquirer – 20 Nov 1891