Inspired by a favorite look from Bally’s Spring ‘24 collection (a surprising hit that season), I embarked upon one of my favorite pastimes: endlessly scrolling through online consignments. I was searching for the perfect 20-year-old dupe of the ensemble’s red-cropped cap-sleeve sweater. The ideal piece would be fitted at the waist, loose at the bust, with a crew, almost mock, neck. And thanks to The RealReal’s vast collection of old St. John, I found it. More so, I found one more addition to my ever-burgeoning collection of pieces that can transition between the many facets of my life—a near-impossible feat.
Subverted by magazines into a buzzy cover line, the hackneyed phrase “day-to-night” dressing has more power than we credit it for. I often joke with my friends about the obscenity of daily rosters we dress for in this city. Once, it was an outdoor barbeque (in February) followed by a late-night birthday party at a heavy-metal gay bar. Another time, it was a sunny park hang before a dinner reservation, and later a birthday party at a cocktail bar. These are, of course, the more far-fetched occasions, but the sentiment applies most times I leave the house, even more so during the holiday season.
A more average occurrence typically involves a day in the office, followed by some sort of evening outing, whether it be an event of work or a personal nature. God forbid, I have a date, then I’ll surely obsess even further. Unfortunately, few items feel as relevant at 9 a.m. as they do at 9 p.m.
So much of my fashion philosophy toes this line between not looking silly, but still toying with the irony of design in a thoughtful way—you can have a sense of humor without feeling like an idiot. Think: designs Miuccia Prada or Phoebe Philo, who, in my opinion, is improperly billed as a minimalist. I am not the girl to put on a skin-tight dress first thing in the morning, I would, however, don a black velvet blazer on my morning commute. Are you following me?
In my scouring, I have found some general winners in this category. Silky fabrics convey festivity, whether they manifest in button-down shirts, A-line skirts, or slip dresses. A jacket of any sort—blazer, collarless, tweed, cropped, etc.—exudes glamour. A luxe trouser in a vibrant print of sumptuous material. And then, of course, the foolproof combination of a pretty blouse and a pair of jeans. Footwear? Forget about it. Heels aren’t happening unless they have a height of below two inches (or a width above that). Aside from the aforementioned red sweater, I rely on a ruched black top from Another Tomorrow, a pair of printed trousers from Loretta Caponi, among others, and then fill in the holes with basics.
The key component in this equation is styling. Show a little skin on one side of the scale, even it out with a roomier silhouette on the other. Beading requires knitwear to find equilibrium. Today (sitting in the office awaiting a holiday party), I’m wearing a sequined purple Loewe pencil skirt, with a striped button-down, and navy knit dickie underneath. This week, I’ve worn a silk blouse with baggy jeans one day and a mini skirt and tights paired with a chunky knit the next. To make it through a full day, you have to offset the party pieces with the mundane—though that’s honestly the goal of most good outfits, anyway.
In general, I find day-to-night dressing is a result of a New York lifestyle, exacerbated further by long commutes. (Friends of mine who live in the West Village have a bit more freedom than the shackles my Bedstuy address locks into place.) No car means no opportunity to go home and change. And I don’t have the wherewithal to pack extra items to swap during the day. New Yorkers (or at least those with an in-person job and without a car service) often have to dress in a manner divorced slightly from occasion and instead lace their “going out-fits” with practicality. Dressing for a multifaceted day requires a deeper engagement with your own closet rather than simply buying pieces for specific events.
In an effort to curate a closet full of things I really, truly wear, the concept of day-to-night dressing is often employed when shopping. The result is funky ensembles that temper the fanciful with the casual. Will I turn heads in the office with my sequinned skirt? Perhaps. Might I be too casual in jeans at the party? Yet another risk, but, as I often remind myself and anyone who will listen, the most important—read: coolest—people in the room are often the most casual.