This Pride Month, as right wing legislators across the United States move to criminalize drag performances, support for transgender youth, and even medical transition for transgender adults, it feels like an appropriate time to make note of the long, long history of drag in America. In Chicago in particular, we happen to know that drag performances as a form of public entertainment were happening as far back as the 1890s. Yes, that’s right - drag’s role in American culture predates airplanes, radios and insulin.

We don’t mention Chicago arbitrarily - as part of this piece on the daring fashions of the “male impersonators” of the 1920s - 30s (what we’d call drag kings, these days) and how to don them, we’re running a giveaway on Instagram right now to win a free pair of Tomboy Toes shoes and a free hardcover copy of I’ll Take Everything You Have by James Klise.

 

I’ll Take Everything You Have is “a vivid portrayal of queer coming of age in Depression-era Chicago, and a timeless story of trying to make your future bright when the rest of the world is dead set on keeping it hidden in the dark,” and we thought the perfect tie-in for a look at some dapper menswear history through a LGBTQ lens. Check out the giveaway here!

Now, on to the fashion!

 

 

Langston Hughes once described the singer, musician and “male impersonator” Gladys Bentley as “an amazing exhibition of musical energy—a large, dark, masculine lady, whose feet pounded the floor while her fingers pounded the keyboard—a perfect piece of African sculpture, animated by her own rhythm.”

She was a fearless performer known for her powerful voice, bawdy lyrics, and, of course, her dapper style. Modern wisdom about all white suits would advise you break up the monochrome with either a tie or a button up in a non-white color; if you’d like to take inspiration from her fabulous aesthetic while keeping it up to date with 21st century fashion, try the all white with a black tie, or a dress shirt in a solid color like blue or dark red. Since white suits are an ideal pairing for warm weather events, this is a good time to break out the light brown shoes for an airy summer look. Of course, if you go with black shoes to hit that high contrast note, we suggest matching it with a black dress shirt and black bowtie.

What about the tails? As much as we love the way they look, suit jackets with tails like Bentley wears in the above photo are pretty rare these days. The modern equivalent is the tuxedo, which is for the most formal of events - so formal that you might not find you have many opportunities to wear anything quite so specialized, which is why a lot of people rent instead of buy on the odd occasion they receive an invitation with the “black tie affair” instructions on them.

Frankly, we think it’s a darn shame - the next time you feel the urge to get your hands on a tailcoat and take it to a wedding or a cocktail bar, we think you should go for it. If anybody can bring back a swooshy garment with a melodramatic silhouette, it’s the queer community.

 

 

Known in many historical circles as the most famous of the “male impersonators” of her era, Vesta Tilley strutted on stage performing as sailors, messenger boys, and fashionable male dandies. In the height of her fame she sold branded socks, cigars and waistcoats with her stage name attached.

With a lot of emphasis on sleek, textural masculinity in her wardrobe, we think some big takeaway tips here are the combination of mid-tone dress pants with multi-textured formal boots, like our Traveler’s Toecaps in Black and their combination of shiny vegan leather toe and matte black wool as contrast. Layer that up with a vest and then top it with a wool pea coat with broad lapels, and you’ve got yourself a very dashing ensemble for fall and winter.

Another useful tidbit to remember about Tilley’s success is the value of custom tailoring; your silhouette is one of a kind, and if you have the money to spend getting suit jackets and dress pants adjusted to fit you perfectly instead of mostly-perfectly, it adds that extra little something to your presence that few can put their finger on but everybody will notice. Just be sure to budget the time for it - there are tailors that can turn around a small tweak in a few hours, but for the sake of safety do your best to have the outfit to them three or four days before any event you expect to need it for.

 

Ella Wesner, born in New Jersey in 1841, started performing drag in the 1870s around the same time that the typewriter and the telephone were being invented. With how complex any individual’s relationship is with their own gender identity and sexual orientation, and with how different the language used back then was compared to language about such things now, there really isn’t any way to know how Wesner might have described herself in today’s terms. What we do know for a fact is that in 1873 she ran off to Paris to elope with Helen Josephine "Josie" Mansfield, an event heavily discussed in newspapers at the time in New York and Chicago, among others, and that by her own request when she died at the age of 76 she was laid to rest dressed in formal menswear.

Although we’ve seen them in every one of the photos so far, we’ve yet to address them: the magnificent top hats each of these “male impersonators” is so elegantly wearing or holding. You may be thinking that hats in general are contentious enough as a fashion choice without going to something as identifiable and archaic as the top hat. Are there any circumstances where a top hat is the right choice, barring a historical performance, a steampunk convention, or a magic show?

The secret, ultimately, is in the swagger. Anybody with the self-confidence to add a top hat to their outfit is going to get compliments and envious looks everywhere they go - even people who aren’t jealous of the aesthetic will inevitably be in awe of the chutzpah. If you come away from this brief glimpse into the history of American drag and find yourself filled to the brim with the need for a hat you can learn to roll down your arm and flip into your hand to impress cute strangers at the next wedding reception you go to, well - let nothing stop you from fulfilling this dream, and remember to either match it to the color of your jacket or your shoes.

Wesner’s dapper looks offer a more general reminder, though; while the chain of her pocket watch is eye-catching and adds a pleasant flourish of detail to her midsection, we don’t need to all go out and buy pocket watches and top hats to learn something from her. Modernizing that flourish, it’s worth remembering that there are so many ways to accessorize (and, in this Pride Month, queer up a little) the traditional masculine formal wear. If you have pierced or gauged ears, you can buy something special and flashy that matches the tone of your tie or your button up. Instead of a tie, you can hop online and find a one of a kind lapel chain or collar chain to put a little metallic gleam at your throat.

Even the tiniest flash of something added to an outfit can interrupt the monotony of a plain stretch of fabric and create a bit of visual interest. The pocket watch is a great blueprint because the dangling chain and shiny-against-matte gives you an example of traits you can look for and take inspiration from rather than literally imitating an outfit.

 

Beyond just fashion tips, what can we take away from this? Perhaps that gender nonconforming people have always been part of society, and will always be part of society - that backlash and moral panic comes and goes, and we can only do our best to remember where we came from, and to remember that our joy and our found families and our sincerity is a powerful source of meaning and motivation to keep going.

We keep building our communities, starting our small businesses, and telling our stories. In hopes of sharing some more of those historical stories of the queer communities, we’ve got a special discount code for you if you’d like to buy your own copy of I'll Take Everything You Have - click here and use code JOE15 to get 15% off until the end of July! (Unfortunately only available for folks located in the United States.) And don't forget we're giving away a free hardcover copy and pair of Tomboy Toes shoes here on Instagram!

Thank you so much for reading; we hope you take this little piece of queer history with you, whether on your lapels or in your hearts, forward into the future.