How to Survive the Last Weeks of Winter in Style

March 22, 2019 | Filed in: Your Closet

Spring may be in the air, but that doesn’t count for much when you’re still tucking an umbrella into your bag, opting for tights under your dress, and leaving your boots outside your apartment door to dry out. And there’s no greater discrepancy between expectations and reality than during the month of March. (Expectation: sunshine flanked by blooming crocuses. Reality: a drizzly hellscape on a mission to give you the worst frizz of your life.) We asked writer Deanna Pai to share her tips for transitioning your wardrobe from winter to spring.

In the winter, you can find me wearing various gradients of black, a look I’ve dubbed “fancy orc.” My boyfriend once laughed at me for packing five gray sweaters and a single pair of black pants for a trip. (Slightly gross but highly efficient, just like me.) To be fair, the sweaters were of different shades and textures, and best of all, I didn’t have to pay a fee to check my bag. But it’s very much indicative of what I wear in the winter: a uniform.

By March, though, even I’m sick of my all-black get-up. It’s like seasonal affective disorder has spread to my wardrobe. Thus, I’m embarking on my next sartorial mission: Shake the SAD out of my style and find a way to put a new spin on my looks for winter—while it lasts, at least.

First, I switch out my coat. I once had a wise manager tell me that in New York, a city of pedestrians, your coat is like your car. It’s what everyone sees first, and therefore your golden opportunity to make a good impression. Fortunately, several years ago I invested in not a cozy parka or blue-chip stock, but an unlined cocoon coat in a sumptuous wool-cashmere blend that I found in Paris.

An unlined coat might be one of the most moronic things to splurge on, because it won’t even keep you warm when you need it. (Alas, I am but a flawed human.) But even so, it’s a well-made showstopper of a coat, and being unlined, it’s perfect for in-between weather; if anything, this is the only time of year that it’s cold enough to call for a coat yet warm enough that I don’t need extra insulation. Aesthetically, it’s fairly similar to the Dougherty coat, and when I toss it on, I feel instantly pulled-together.

Another bonus of a lightweight, unlined coat is that without the thick insulation of my winter parka, I can pile on layers underneath without ever feeling encumbered or like an anthropomorphic marshmallow.

Speaking of: Next, I swap out my sweaters for layers. I love the ease of sweaters, but the one-and-done aspect that I usually appreciate is also what makes them a little monotonous. Plus, layers allow me to better regulate my internal temperature when it’s still chilly outdoors and warmer inside. After staring at the inside of my closet for several hours, I recall that have a ton of tanks in summery fabrics, like cotton and silk, perfect for layering, and I begin wearing them in a rotation.

For one work event, I wear a tank splashed with orange and red under the Woolf jardigan in black, while I pack a silk leopard-print tank for a trip abroad. Both go perfectly with black jeans and boots. I know, I know—that’s still a lot of black. But it’s not all black! One small step for me, one giant leap for my look. I’m so inspired that I even layer on eyeshadow, which I usually save for special occasions.

At this point, I feel like I’m making progress. There’s a fine line between uniform and style rut, and I’m getting a much better sense of the side to which I’ve fallen in the past few months. Wearing a pop of color makes me a feel a little more creative when I’m working—maybe because I now actually have to think about my outfits—and looks even bolder when paired with my usual black pieces. Imagine a rich, vibrant color, like the Lise top in deep plum, against an all-black ensemble. It’s an effortless way to make a statement.

I begin cycling in other layers, including a gray, shawl-neck cardigan (it’s a very pale gray, in my defense) and a silk jacket with—brace yourself—a floral pattern! Layering gives me the opportunity to play with textures, too. Wool can work wonders under a blousy silk jacket, while my silk button-up shirts, conversely, look so fresh under a leather jacket that you might even think that I brought them to a dry cleaner.

Before we get carried away, I’ll note here that my pants stay the same. Old habits die hard, and I just cannot retire my black pants or joggers just yet. I do own a pair of patterned joggers, but they’re still a little overkill for this time of year. I’m not a season-pusher. The most I can muster is a nudge.

The next order of business: my shoes. My many salt-stained pairs of boots need to spend some quality time with my shoe-repair guy ASAP, so in the meantime, I reach for…sneakers. Don’t worry, I’m not going normcore on you, for these are not just any gym-bound sneakers. They’re minimalistic white sneakers with black details and clean lines, and I’m convinced that they give my overall look a more edgy, I’m-a-cool-entrepreneur vibe.

And while ballet flats may be your first thought this time of year (if not heels stashed under your desk) let me ask you this: Have you ever had to walk around in water-logged flats, hearing a squish with every step you take? Because I have, and it’s torture. One of my rules of dressing for the end-of-winter doldrums is to expect precipitation at any moment—the price I’m paying in boot repair upholds said rule—which is why I insist on these relatively water-resistant kicks, and navy rainboots if it’s clearly monsooning.

Switching up my style has had an added perk in that I’ve dragged most of my spring-appropriate pieces out from under my bed, which makes the usual transition a no-brainer. In fact, dressing away the sartorial SAD has been my transition this year. Oh, is that the sun? Does the forecast say 50-degrees? Let me just take off my coat.

Ready to embrace spring dressing? Shop our latest collection, “For the Win.”