Diana Vreeland’s “Why Don’t You?” For Transmascs

Diana Vreeland, famed fashion writer and editor for Harper’s Bazaar and Vogue, had a regular column in the former titled Why Don’t You..? She started writing it early in her career, in the summer of 1936, and it helped establish her reputation. In this column, she floated whimsical, eccentric style ideas that were best enjoyed as concepts, not as lifestyle choices. Each suggestion is written as a fragment, picking up where the title left off. They’re full of striking images: a commonly quoted example is, “[Why don’t you] Rinse your blond child’s hair in dead champagne to keep it gold, as they do in France?” The phrasing is chosen for maximum dramatic impact, invoking powerful fashion staples like death, blondeness and France.

Other advice from Vreeland is more grounded in practicality. She wonders: why don’t you buy two sets of the same pair of shoes, “except that one pair has thin rubber soles for damp days? Any cobbler can put these on.” This advice focuses more on a way of doing things than a specific style, and could be a real game-changer for someone who usually wears shoes with leather soles and has cash to burn for the sake of creating a more cohesive public persona. The ideal reader is definitely a member of the leisure class.

The overstated opulence of most Why Don’t Yous makes them distantly unattainable to many actual readers. Generally, the ideas are precious, hard to execute, elaborate and expensive. To put them into action would require prohibitive amounts of money or time, and they skew in a frilly, maximalist direction. But the column also offers a sense of playfulness instead of presenting a narrow view of acceptable fashion and lifestyle choices. The same distance that could be alienating also helps the work avoid the usual cloying judgment in fashion advice.

Excess sets the column outside the bounds of scolding articles that tells you which items of clothing to wear, what to combine them with, how to choose a flattering outfit. The fantasy aspect exists apart from the pressure and expectations that often come with unsolicited advice on self-improvement. It encourages you to take risks in pursuit of unexpected ways to bring glamour into your life. In a holiday edition of the column, one gift idea is buying a linen tablecloth and having it embroidered with bon mots, all in different colors.

In the 2012 biography Empress of Fashion, she’s quoted describing the effort as “just ideas. It was me, insisting on people using their imaginations, insisting on a certain idea of luxury.” Harper’s Bazaar posted a modern incarnation of the column on their website in 2014, and it included plenty of promotional links that remove the guesswork of finding your own cobbler or brand of shoes. In the original, the specifics lie in the garment material or the thread color, but rarely in branding.

There’s something appealing about this kind of voice, breezily making off-the-cuff recommendations to you while insulated by money and luxury. She imagines for you a life where you can find the resources to be stylishly eccentric and frivolous. You don’t need to actually invest hours of your time into these ideas; it’s enough just to imagine them and think about small ways to nail down your own personal style. Whenever someone makes a suggestion to me that has no foundation in the realities of my life, I like to imagine it in Vreeland’s voice to make it a little more tolerable.

As I navigate my gender and try to make it fit in with my plans for life, I imagine advice in the tongue-in-cheek manner that distinguishes Why Don’t You columns. So much of being trans consists of facing harsh reality, and advice geared toward glamour provides a calming contrast. Plus, I like the idea of taking inspiration from a classically feminine figure to direct my fledgling masculinity.

Here’s how I imagine the column would have gone, if Diana Vreeland had a transmasculine audience in mind.

Transmascs: Why don’t you…

Cut up old dresses and turn them into scarves, pocket squares and belts? If you love the print of a dress you own but can’t bring yourself to wear it anymore, you don’t have to give it up entirely.

Cut your own hair, badly, so your hand is forced and you simply must get it cleaned up in a salon?

Bring in a photo of a long-dead movie star to your salon, insisting that he’s the point of reference for your next haircut?

Select a large coat that obscures your figure with faux fur, voluminous folds of wool or all-over fringe? Such a coat is easy to slip on and settle into, and it lets you take up space and fill up store aisles.

Buy your shirts from the little boy’s section of the nicest store you can afford? Pure cotton feels better on your skin, ages more gracefully and biodegrades more easily in the landfill, when its time comes.

Learn to hem pants, so you can focus on waist size and ignore inseam, freeing yourself up for exciting new trouser adventures? If you’re a size that’s uncommon in cis men, take advantage of end-of-season sales to build up your wardrobe, and forget about the long legs. You can deal with any extra inches of fabric later.

Research military history in your family’s country(ies) of origin with the goal of finding an identifiable transmasculine forefather?

Tear the frills off an old shirt and repurpose them as a jarbot?

Ask your boyfriend to teach you how to shave? This is a uniquely sexy possibility available primarily to transmascs. Take advantage.

Go to the biggest city near you and pick up a library card, so you can get access to their superior digital services?

Take your collection of old, beloved post earrings and use them as lapel pins or cufflinks? If they’re gathering dust in a jewelry box or drawer, put them to use in defining your new style.

Set up a shrine of your favorite transmasc historical figures around your mirror and look at them while you get dressed? Remind yourself how eternally stylish and good-looking your people are.

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