Five
First Impressions, Money, and Destiny: Power Dressing for Peasants

It is a strange fact in life that to get a job that improves your income you must dress as if you have a massive fortune in the first place. Well, it does pay to look refined (if not rich) and that is the cornerstone of power dressing. It is a term I despise but have come to accept, given that clothes are one of the quickest ways to serve up a flash impression, even if it is an outright lie. I once gave a lecture to a group of socialites at a fancy lunch hosted by Hermès of Paris. I told pithy anecdotes, used passable French, and held the floor for forty minutes. At the end of the talk a woman in a Balenciaga jacket rushed at me, leveled her chin, pointed to my trousers, and said, “Darling … your zipper’s broken!” Which just goes to show, if you mess up one detail, you mess up the lot. I may as well have spoken nude on horseback.

The Miss Priss job interview outfit used to be an afterthought in my wardrobe, a sort of grooming lottery involving blazers without food on them and dresses with hems and buttons intact. Now I have a uniform and it hangs inside its own neatly zipped bag right at the front of my closet. It consists of a pair of polished chocolate brown Mary Janes with a two- and three-quarter-inch heel, two pairs of sheer smoke-colored tights, a green silk print seventies’ dress, a brown leather belt, and a brown linen jacket. For really formal occasions I have a matching skirt for the suit jacket, a black cashmere V neck pullover, and a tiny Hermès scarf. A separate glossy handbag with everything needed from fresh lipstick to business cards is also there, in a clean cotton drawstring bag. This emergency kit is like a piggy bank. I know I can shake it open and run out to lunch, a meeting, or an interview without the anxiety of feeling shabby.

Sure, it’s a front. Work wear is a lot like drag. Unless you actually work in finance or law, it feels odd to dress more formally than is natural or more uptown preppy if you are downtown rock chick to the core. The common misconception about interview clothing is that there is a blueprint look for success. In fact, every industry has incredibly subtle nuances of style. Often when dropping off a portfolio or résumé at an agency or magazine where I’d like to be hired, I’ll scope everybody from the intern by the watercooler to the front receptionist to the CEO behind a thick glass door, and I’ll be taking notes. And stealing looks wholesale.

I once had this extraordinary boss named Herbert Ypma. “Call me Herby,” he said with a purr. He dressed like a Ralph Lauren model and had a chiseled face like a hero from a Fitzgerald short story. He could sell tea to China because he was always … crisp, clean cut, and ready. “Listen kid,” he’d say from the side of his sensuous, speeding lips, “you gotta dress the part till you get the part, and in the meantime bite off more than you can chew …”—a well-timed dramatic pause here—“and chew like hell!” He loved the power of positive clichés and made most of them come true: mainly because he was punctual, his tie was always ironed, and had a glamour that was oddly contagious. When I worked with Herby, selling advertising for his magazine and editing a twenty-page arts section, I wore a canary yellow linen suit, an emerald green suit, and lots of little black dresses. Bidda-boom, bidda-bang. He taught me, in a very Dale Carnegie way, that the first impression is often your last chance at impressing—and there is no such thing as looking too slick. Today Herby is famous for his photography and his great series of books, Hip Hotels. I think of him every time I enter a meeting, give someone a super warm engulfing handshake, and know I’ve dressed the part. Bite off more than you can chew, baby—and, hey, call me Anna!

Commit to Your Career in One Outfit

Women often leave work and business clothes as an afterthought. It’s the one area of fashion that seems to stagnate in convention. We will wear a gray shift dress or a dreary little black suit even if it doesn’t reflect or suit us, just to meet some corporate norm; or we’ll buy some random interview suit on sale and chuck it in the closet without love or thought. Meanwhile, fashion focuses so much more aggressively on seduction—killer heels and plunging necklines abound. Strange, because if one considers survival (and creative fulfillment), the most important encounters in our lives are actually job interviews and chance meetings that lead to better work … not first dates.

What Looks Like Money

Part of getting a job is looking like you don’t need one and dressing a little richer than you are. It’s the ultimate savvy chic. And the secret with that is simple: dress a little plainer than you’d like. Chic, as we all know, is a restrained rather than a flashy art. Looking rich is more about texture and proportion than actual explicit signals like gold buttons or giant handbags. To get on the wrong side of rich-girl chic look at the girls in the eighties’ movie Heathers. And to get it right, look at anything worn by filmmaker/mother/style queen/muse and style-maven Sophia Coppola. She always wears a fancy dress with the simplest hair and a rather bare makeup style. It’s very French, that risk of looking plain, but the understatement is always underscored by some element of luxury: buffed nails, smooth pampered hair, a cocktail ring the size of an ostrich egg. The ideas that follow would make most real heiresses shudder, but here’s my shortcut to putting on the Ritz for pennies.

Breaking the Classic Suit in Two

Suits can do strange things to the body. Too many buttons make you look like an overstuffed gourmet sausage. A badly set sleeve can look boxy, and a skirt that’s too tight defeats the purpose altogether. If your interview is not for a very formal, corporate position I recommend the following tactic: start with wearing one element of your suit at a time and using families of color and tone to unify an outfit instead. I think using the same tone or color in different textures looks chic: a chocolate skirt in slubbed silk, a cashmere sweater in the same tone, and a linen jacket in a contrasting but complimentary shade such as violet or burnt orange. This style code obeys the law of coordination without looking too square. Suit jackets make a crisp blouse and flat-front tuxedo-style trouser look brilliant, and you can add to that with a short silk men’s tie. Button-front shirts look smarter (and less sloppy) than camisoles or shell tops—but look for them in brilliant colors because ones in white or pinstripe, when not tailored or made of good quality fabric, look cheap.

If you want to wear a suit, choose one with a low-cut front and really well-cut shoulders, and have the cuff altered to sit right on your wrist. This simple change makes a suit look custom fit. Spend as much time on finding a suit as you would on a pair of jeans, and then see how the jacket looks with jeans. If you can afford it, invest in two suits, because having a backup is priceless and variety makes the rounds of job interviews slightly less painful. Last but not least, sew a lucky penny inside the lining of one pocket. Why? Because style is nothing without a little magical thinking.

Grooming the Threadbare Career Girl

“Shoes and nails, darling, shoes and nails!” That’s the mantra of my girlfriend Robin Bowden, who went from textile fashion maven on Seventh Avenue to property guru as senior vice president of Douglas Elliman in the swing of a spiffy hand-polished brogue. She swears it’s the extremities that bosses always notice first. So in that spirit, I keep my nails and shoes buffed and check the soles, straps, and laces of regularly worn shoes once a fortnight. Handbags, in turn, revive (and survive) if you empty them nightly, clean their linings, and store them in soft cotton bags (I use pillowcases) rather than leaving them full of office gear, hanging from a strap.