Putting together an autumn wardrobe? Here's how to truly be yourself

Simon Doonan, the fashion pro, professional contrarian and author of How to Be Yourself advises us all to dig deep and find our own personal style
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Young Thug, one of Simon Doonan's examples of good self-expression. From How to Be Yourself
Young Thug, one of Simon Doonan's examples of good self-expression. From How to Be Yourself

Simon Doonan, the writer, media personality, fashion authority and author of our brilliant new book, How to Be Yourself,  knows a thing or two about clothes. As a former window dresser, Creative Ambassador-at-Large for Barneys department store and style columnist for Slate and the New York Observer, he understands the seemingly simple, yet actually fairly complex task of putting together a personal wardrobe - a job many of us take on, as summer turns to autumn. 

So, how does one do it? In Doonan’s opinion, a lot of it comes down to being yourself. As he puts it in How to Be Yourself, you should really establish a signature look before you hit the sales racks. That might sound simple but “in many cases this involves a certain amount of effort and imagination, a certain investment in time,” he writes. “This is time well spent. Once you establish the outward appearance—the formula, the uniform, the recipe for your very own look, the look that best expresses your essence— it gets much easier. Land on your signature look, and don’t be scared to rinse and repeat.”

Personal impulse is a good place to start. Doonan cites his own mother, Betty, an Irish immigrant in mid-century south-eastern England, who “With the aid of her cosmetic artistry, well-chosen brassiere, crisp blouse, white pencil skirt, seamed stockings, and a sassy heel, would transform herself from an average broad into a confident head turner.”

Betty Doonan. As reproduced in How to Be Yourself
Betty Doonan. As reproduced in How to Be Yourself

This was quite out of keeping with local sartorial norms. “The goal was to avoid appearing attention seeking, or—the biggest crime of all—tarty,” Doonan writes. “As a result, our neighbors looked relentlessly, and similarly, respectable. Only Betty, the uneducated outsider— the lowborn Irish interloper into English respectability— actually dared to be different. Why? Because she was different. The look that Betty created—bold, nonprissy, and memorable, recalling the badass heroines of film noir—was a perfect piece of self-expression. Her inner self and her exterior glam’d-up self were in harmony, two components of a fabulous whole.”

Confidence helps one do this, and much of that confidence comes with age. In his new book, Doonan lists just a few of the individuals he feels have managed to be themselves, sartorially speaking. “Stylish, iconic, and authentic, this wide-ranging group includes people like Bill Cunningham, Lena Dunham, Keith Richards, Angela Merkel, Meghan Markle, Adele, Sasha Velour, Chip and Joanna Gaines, Emmanuel Macron, Whoopi Goldberg, and Diane Keaton— individuals, incidentally, who have had a huge influence on the styles of others,” he writes. “It skews older because young people—the Justin Biebers and Katy Perrys of the world—are still seeking their true selves; as a result, they experiment and change their looks and are hard to keep track of.”

Simon Doonan. Photo by Joe Gaffney
Simon Doonan. Photo by Joe Gaffney

There are, of course, a quite a few exceptions, such as the rapper Young Thug. “He is always, regardless of the hour, relentlessly and fabulously himself,” writes Doonan. “If clothing is nonverbal communication, Young Thug’s appearance speaks loudly, and says, ‘I am an unstoppable creative bad boy who celebrates style, fantasy, opulence, and decadence.’”

This might feel like too lofty an example to follow, but all of us can at least try a little self-expression, beginning with a little colour theory, which can either blend or clash with our interior and exterior tones. “I, myself, was once a big fan of chocolate brown,” Doonan reveals. “I liked the louche ’70s vibration. Then my hair went gray, and my choccie browns lost their luster—gray and brown is very aging squirrel, if you know what I mean—so I switched my allegiance from brown to navy, a lovely adjacency to gray hair. Bam! It worked: I went from a senior squirrel to a silver fox. I often wear my navy duds with bright orange or hot pink. Most of us pick out colors based on mood or context. As the late great fashion designer Pauline Trigère once said, ‘When you’re feeling blue, think red.’”

Allegiance to one single colourway or look for years on end can be tough, but it can also pay off. Doonan cites designers such Tom Ford, Donatella Versace, and the late Karl Lagerfeld, each of whom had “the wisdom to stick with the same look, “he writes. “Sticking with the same look, especially in the whirligig of the fashion world, takes courage and nerves of steel, but the dividends are massive. Recognition and iconic status will never be yours if you keep road testing new styles.”

None of us need to display quite that profession-league level of dedication when getting a look to suit us. Doonan advocates affordable, simple gestures, over big-ticket items. Slip in simple things, such “as a raspberry beret, a vintage Boy Scout woggle on your scarf, a particular manicure, a blue French worker’s jacket,” he suggests.

Robert Mueller. Image courtesy of The Federal Bureau of Investigation
Robert Mueller. Image courtesy of The Federal Bureau of Investigation

And if you don’t feel flamboyant, your look needn’t be flamboyant. Ill-conceived austere-look can work too. Consider Special Counsel for the United States Department of Justice Robert Mueller. “He serves extreme rectitude and Waspy realness,” writes Doonan. “You won’t catch him chilling in a leopard jumpsuit. His fabulously old-school style comprises a veritable orgy of Brooks Brothers preppiness: white button-down Oxford shirts, navy suit with a center vent, side-parted steel-gray Kennedy hair. Remarkably unremarkable, devoid of anything tacky or parvenu. The payoff, especially for a lawyer like Mueller, is his aura of timeless credibility and gravitas. Is it part of a cunning strategy? I will wager that he dressed like this when he was five years old. This is who he is.”

And even in this case, the details make the look. “His Casio DW-290 sport watch, for example, tells us everything we need to know,” writes Doonan. “His is a life of function and service rather than self-indulgence. He is the anti-Liberace.” Be yourself, then, and the rest of the look just falls into place. 

For further advice from Doonan on every subject from love and money to careers and interior design, order a copy of How to Be Yourself here.


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