DRESSING APART: Daytime dresses and a New York state of mind

When I was a teenager (in the mid-1990s), I used to say that I could wear jeans and still be overdressed. It was the unfortunate era of alternative grunge, yet I was the alternative one—as I clung to miniskirts and biker boots or maxi dresses and platform sandals, the hipsters of my day embraced layers of flannel and cotton waffle tees, sporting dirty hair and even dirtier denim. Even on a casual Friday, my Gap jeans didn’t cut it; maybe that’s because my mother insisted on ironing my Pearl Jam concert T-shirt. I consistently looked like I’d just come from the cleaners.

The ever-wrinkling casualization of fashion has long eluded me. Growing up in the south, I was schooled in the principles of dressing for dinner and wearing lipstick to the grocery store. Now happily encamped in easy, breezy San Francisco, I am still a last bastion of hope for certain classic mandates: the belt should match the shoes; a black turtleneck is always elegant; and yes, there is such a thing as too much jewelry. Technically, I’m too young to be mired in such traditional cliché. But I’m fastened to a time-honored perspective of style and beauty that celebrated hip-to-waist curvature highlighted by architectural fashion. My shoes and hair are usually polished, I rarely wear jeans and, in my little black dress uniform, I am often overdressed in comparison to the crowd—that is, unless I’m in New York.

New York State of Mind

In San Francisco, the “day dress” of Vogue photo shoots rarely has a place. As a former fashion editor, I assign these dresses to the ladies who lunch for various charitable causes or, occasionally, to the trendy PR gals (many are also ex-editors) who called at my desk with samples from their latest jewelry client. Recently off the plane from a work-hard-shop-harder excursion to Manhattan, however, I discovered that the day dress is ubiquitous in New York and, for once, rejoiced in the knowledge that I had packed correctly: four day-to-night dresses, one gladiator sandal, one sky-high platform and gobs of costume jewelry.

Back at home, I feel more compelled than ever to dress for the part I want—that is, a well-heeled gal about town with the time and money to pull herself together. Not that I have the time—or, less frequently, the money—but donning that Victor & Rolf skirt (scored at Century 21) for an afternoon mani/pedi with mom has three rewards: I feel like a million bucks (even if I only paid $250); mom says I look like a million bucks (even if she notes that my clutch does not match my shoes); and an ex-coworker, who I bump into at the front door of the magazine where I too used to slave for 12-plus hours a day, says I make her want to quit her job (freelancing has its perks).

As I notice her leggings (or were they sweatpants?) tucked into Ugg-like boots on a Thursday afternoon, I once again realize that my particular approach to dressing is completely foreign in the Bay Area. Even after four years living in this corner of the world, heralded for its ultra laid-back sense of ease, I can still count the number of “hope I don’t see anyone I know” days as few and far between. (Thank god for the coming of stylish stretch pants: “I just came from pilates” is a brilliant excuse for wearing your pajamas to the mall.)

For years, I have fought the urge to iron my jeans and straighten my hair on weekends—and often my plight gets the better of me. I yearn to hit the Saturday morning farmers market with that rumpled “natural” look typical of European models, and I wonder why I can’t attain the effortless denim-and-diamonds chic of always-perfect Parisian women. But being in New York, with my fellow day dress people, I’ve decided just to embrace my overdressed self. Yes, I will forever be inundated with questions—“Why are you so dressed up?”—but at least I’ll know I’m being true to myself. Because for me, it’s not just okay to get dressed up—it’s a pleasure.

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