A PHOTOGRAPHER I work with revealed an uncomfortable truth the other day. “That outfit is so… you!” she chirped. I can’t remember the outfit exactly; it may have involved a swing jacket and a skirt with leggings. It may have involved pigtails. Then: incoming. “I love how you don’t dress your age.”

What did that mean, dressing my age? To my consternation, friends in recent years have begun to brandish the phrase in the context of whether their hair was too long or their sleeves were too short or their jeans were too low rise. The notion that one’s apparel could be pronounced inappropriate according to some universally accepted but unwritten age matrix hadn’t occurred to me. (It wasn’t the first memo I’d missed. Marrying for money had never occurred to me either.)

I have always dressed according to an inner compass set to my spotty grasp of current fashion, a desire for self-expression, and an essential frugality. High fashion was out—too pricey, too prescriptive. Late-model vintage was, too: I already expressed myself that way in the ’70s, ’80s, and ’90s, thanks. A few guidelines served me well, such as: If you love it, you have to buy it. If you buy it, you have to love it.

These were my polestars, which combined into a look that might be described as casually classic with the occasional youthful flourish (whimsical, or vaguely bohemian, or possibly just ridiculous). It has required a fair amount of daily invention, which sometimes means spending an inordinate amount of time in front of the mirror—particularly when I was younger and had ambitions professional and romantic to work in. It has packaged me acceptably for years.

But now that dressing my age had made its way into my head, I began to second-guess everything. Is flirtatious out? Well of course, I realized with horror, blushing to think of the whispers of lace and décolletage I’d revealed in pursuit of “coquette” that had probably been landing me closer to “cougar.” Aaaack! Had my attempts to look sexy actually been making me look like a drag queen?

Worse, does my aging physique betray my efforts altogether? Where youthful attire always works for the ingenue, right down to the adorable little muffin-top spilling out over the waistband of her tight jeans—the practice is only acceptable for the mature woman with the bod for it. Nothing conveys this predicament more painfully than the sadistic makeover TV show, What Not to Wear, which I winced through recently. “YOU HAVE NO NECK!” screeched the she-viper host to the middle-aged guest whose life she was improving. “What were you thinking when you bought that dress? It only highlights the neck YOU…DO…NOT…HAVE.”

Pity the poor neckless creature if she tried to rock a little street fashion or, worse, dress ironically. The New York Times recently highlighted a sartorial curiosity from the quinquagenarian Madonna—blue minidress, thigh-high platform boots, taffeta hair bow vertical as a radio tower—to ponder whether women of a certain age can still deploy fashion to deliver an arch wink. It will more likely deliver her to the peanut gallery, the piece concluded. On a platter.

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Mind you, I don’t dress ironically, at least not intentionally. But what are my options? I asked myself on a recent fall shopping foray, wandering rudderless through the streets of downtown. Am I now the official property of Eileen Fisher? Ready for the “I’m a hip grandma!” packagings of Coldwater Creek and Chico’s; the stalwart Daughters of the American Revolution tailoring of Talbots? Could I even enter H&M?

I sought sanctuary at the Euro-chic boutique Baby and Co., whose buyer, Jill Donnelly, embodies both style and maturity. “You do have to work a little harder as you get older to make yourself look fabulous,” she sympathized. Many women suffer from what she terms “the disconnect”—when personal style doesn’t reconcile with their age. But at the other extreme are the women who embrace the gifts of maturity. Charm. Wit. Manners. “A knowingness,” Donnelly called it.

I thought of my mother, as classy a woman as ever elevated a cocktail party sheath, whose style seemed to spring intrinsically from her identity. Her identity—not her age. A couple years before she died Mom confided how startling it was to look in the mirror and see a 70-year-old face looking back. “Because honestly,” she marveled, “the woman inside me is 20.”

From out of nowhere I wondered how I would dress if I didn’t know how old I was. Donnelly couldn’t have been more dead-on about knowingness. The point of dressing isn’t to reflect your age. It’s to reflect your soul.

From where I stood on Fifth Avenue I could look through the shop windows of Betsey Johnson, where I saw fleets of young shoppers eagerly hauling armfuls of silk chiffon and crepe—back satin minidresses in and out of the fitting rooms. How exhausting it was back in the days when I labored that hard to dress for success, or—like these hotties—for conquest. It may be true that it gets harder to look good with age, but dressing for my unformed younger self took far more effort.

My focus shifted and I saw myself reflected in the shop window. I recognize that woman, I thought. Now more than ever in my life—and owing directly to my… maturity—I know who I am.

I am a middle-aged woman in pigtails.

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