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A fresh approach

Eight ways to strategize your winning style

(clockwise from left) Mary Katrantzous white bib and petunia dress, Stella McCartney sneakers, Mary Katrantzous dress, Free People beret and socks, Maje dress, Chanel dress,

Photos courtesy of vendors


“I have eight options,” my husband recently explained to me. He was talking tennis. “When someone hits the ball over the net, I choose one of eight ways to try to win the point.”


I was listening.


“I don’t work with just one, but I don’t try to imagine as many that physics will allow, either. I work with eight. I cycle through them and then choose the one that should work the best.”


He finished talking and then something strange happened. I didn’t say a word. Then something even stranger happened. I didn’t think about me, about how I make decisions in a crunch. I stood in silence appreciating what he had said, this concept of mental processing within a finite set of choices, of operating at some point between (a) having no choice at all and (b) sweating through an infinity of alternatives. To put this in sartorial terms, his decision-making system was more flexible than Steve Jobs and his black turtleneck, but less open-ended than a Cher Horowitz wardrobe so extensive that it demands a closet algorithm and a password in order to get dressed for school.


I was impressed. I didn’t for a second wonder how my husband came up with eight options. I should have, I suppose, but I have for too long been living in a land of metric measurements and dinner parties that start with stopwatch punctuality. Here the sales tax is included on the price tag. We take a number even at department stores. There must have been some reason this man chose a specific number, I was certain, but things were already returning to normal in my head. What about me? I wondered instead. How could I use this concept in my life?


The answer came as I was reviewing the most recent runway and fashion apps. So much beauty, I was thinking, so much delight and life. I cleared my hangers and drawers of all things tired and promised myself I would try to follow a similar system. I would try to make my new fashion choices based on a protocol of eight. I just wasn’t sure which eight.


The first thing I did was to write out a list of what I knew: the established categories of apparel by type such as tops, pants, gowns. It was easy. I could get every type of clothing aligned within eight columns as long as I mashed most of life’s necessities like shoes and purses and hydrating lotion into a catchall category labeled “accessories.” But then I studied it. The list was nothing more than a collection of parts, and not one of these parts could, on its own, produce in my head an instinctive, quick, winning combination. There had to be another way. Then I was distracted by a Chanel ad. Then my daughter showed me a pair of sunglasses. Then I watched a woman walking down the street in a long, shiny olive-colored skirt—the martini kind of olive, and I knew what to do. I knew my eight.


Ellery print dress, Rochas Margo brocade top, SockSeason finesse sock



Create a look around volume. Volume is about size and sound. It can be about grafting a narrow silhouette onto something more majestic. It can also be about color and the personality of the textile, loud—a shiny bold print—or quiet—a plain beige linen. Volume can be something vibrant or something more discreet. Volume is about balance and complements and visibility however visible you choose to be that day. A quick decision-making tip: look at your reflection from a distance. If all you see is the outfit, you may have a balance issue. A well-balanced “look” from your feet to the top of your head should ultimately lead people to your eyes. Every outfit should lead people to your eyes.



Focus on fluidity. Go crisp, think soft, allow a drape, or set the stage in power edges. Fluidity is about movement, about mixing hard with soft. Fluidity is not just about how the clothes react to your movement, but about how your body adjusts when you are in them. Quick decision-making tip: don’t just stand and spin in the mirror. Runway your outfit.

Clockwise from top, left: K-ourage pant, blouse, and skirt;  Ellery earrings



You have your basics, now finesse it. We know what finesse looks like on others. It looks like money and security, a cool attitude, or at the very least adorableness. Pulling it off could be as easy as a piece of jewelry, the perfect shoe, a lifestyle bag, a hat that looks good. Accessories do not have to be delicate, but they do have to be consistent with the overall tone and allure of the look. Quick decision-making tip: An accessory is not a prop. If it distracts you in any way other than thinking, “omg I love this,” then try again.


Paperselfs eyelashes



You are wearing this season’s tiny, tiny sunglasses and a beret. This means you are in Paris. Or you are wearing something from an older period, more medieval. Or you are living in the future and in the desert. Or you are a little of all of the above, wearing a Crusades-inspired tunic with a sun protecting hoodie, looking like you are about to do battle against the Death Star. Whether fiction or non, you are the narrator of whatever story you wish your fashion sense to tell, your own private adventure, with all the possibilities to step in and out of a character. Quick decision-making tip: blend in a bit of the familiar. Incorporate one item from your very real present day world to keep the clothes your choose for your dream job, dream date, or dream strut from looking like a costume, and to help you stay relaxed.



Zero in on the details. A well-constructed piece of clothing carries its own weight. Tailoring, lining, appliques, and inspired fabrics mark a savvy fashion philosophy. Quick decision-making tip: read the label, look at the item inside out, and then put it back on the hanger. Step back to inspect and ask yourself, does this look like something that deserves me?



Oh, the joy of being practical. And it is a joy, especially when it taps down any guilt over spending money on you. Can I multitask in that outfit? Can I make small changes for big effect? Does it pack well? Efficiency also means asking for style advice. An engaged storeowner or clerk will look at you—your shape, your coloring, the way you move, maybe even the way you talk to others in your entourage—and begin to connect you up with items in the fashion lines they carry. They will make recommendations, and of course you may try these items on and decide “Just not me,” which is fine. At least you tried. But if you never try, if you insist on sticking to what is familiar, then you will miss out on one of the most truly gratifying shopping experiences of all time: surprise, followed by amazement, followed, ultimately, by a compliment offered by someone who is under no obligation to be nice. Quick decision-making tip: run a cost-benefit analysis. Can I justify buying that lingerie? The answer is always “Yes.”


Gold Doris sunglasses



In addition to being sun-smart, as well as cycling-, gardening-, and sailing-smart, be prepared for a change in wind and rain and temperature. Quick decision-making tip: treat outerwear purchases just as you would any other type of outfit. This means buy many and make sure they look like you almost want it to rain.



This is the option that always catches me off guard. I think of it the least, but it works the best. This is not about buying something with the thought of working yourself into it. This is about rewards. You’ve cared for your feet. You’ve sweated through Bikram. You’ve worked lotions into your skin. And you’ve figured out how to shape your eyebrows without scaring the kids. Inspiration is a reward for being faithful to a tedious routine of self-care, because Inspiration is about the ability to slip something on—expensive or not, trending or not—and go out knowing you are on the top of your game. Quick decision-making tip: only buy it if you can wear it out of the store.


Those are my eight options. The ball is now in your court.


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