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.