Style

10 Undeniably Cool Winter Outfits, According to New York City’s Best-Dressed Ladies

For every souvenir shop in New York City, there are twice as many well-dressed women; they’re everywhere. I keep a running note on my phone to jot down pieces I spy on others to remember for future shopping trips. (Today, I wrote “green velvet pants”…. You had to be there.) It’s an amazing thing to witness, particularly at this time of year for someone like me that struggles to dress for cold weather. But in New York, there’s no shortage of winter outfit inspiration.

And that brings me here. I keep tabs on what celebrities are wearing out and about for my monthly best-dressed column, so I couldn’t help but notice an influx of fabulous ensembles over the last few months. Ahead, see and shop 10 winter outfits that celebrities have recently worn in New York.


Layer, Layer, Layer

new york, new york december 10 emily ratajkowski seen walking in new york on december 10, 2024 in new york city photo by michael simongetty images for the loft entertainment

Michael Simon

What’s more NYC than Timberlands? Nothing. If you missed your chance to snatch Emily Ratajkowski’s Mango sweater with a built-in scarf before it sold out in your size, fret not. This outfit formula is easy to make your own with pieces you probably already have in your closet—and her Gap jacket is still shoppable, too.


Elevate Casual Staples With Leather

new york, new york december 17 lily rose depp is seen in midtown on december 17, 2024 in new york city photo by thestewartofnygc images

TheStewartofNY

Seeing Nosferatu changed me as a human, and I’ve been watching Lily-Rose Depp’s laidback style with a keen eye since then. Her Y2k-esque Chanel bag will live on my wish list forevermore.


Double Down on Denim

new york, new york december 13 bella hadid is seen on december 13, 2024 in new york city photo by thestewartofnygc images

TheStewartofNY

I haven’t stopped thinking about this 2002 Roberto Cavalli denim skirt set since Bella Hadid wore it in December 2024. Unfortunately, the exact ensemble is hard to come by, but you can take inspiration and double down on denim for an instantly chic outfit formula this winter. Plus, Hadid’s exact glasses are available to shop for just $27.


Invest in a Faux Fur Jacket and Tights

new york, new york january 13 suki waterhouse is seen in tribeca on january 13, 2025 in new york city photo by thestewartofnygc images

TheStewartofNY

I, for one, am certainly not brave enough to wear denim cut-offs in the dead of winter, but damn, Suki Waterhouse does make me want to try it. This is a look fit for a rockstar straight out of Daisy Jones & The Six.


Tailor Your Look to Perfection

new york, ny january 13 brooke shields is seen leaving the abc television studios on january 13, 2025 in new york city photo by xnystar maxgc images

XNY/Star Max

Brooke Shields was my first girl crush for her role in Disney Channel’s 2005 flick Bob the Butler, a movie that seemingly only my sister and I watched. All these years later, she’s still a vision in a fitted suit and metallic pumps.


Keep It Classy

new york, new york january 04 olivia munn is seen in tribeca on january 04, 2025 in new york city photo by thestewartofnygc images

TheStewartofNY

Leather pants? Check. Sunglasses? Check. Black boots? I wouldn’t be caught dead without ’em. Olivia Munn’s timeless outfit is as replicable as they come. Don’t be afraid to play around by adding fun accessories.


Play With Power Prints

new york, ny december 18 kerry washington is seen arriving at the view show on december 18, 2024 in new york city photo by mediapunchbauer griffingc images

MediaPunch/Bauer-Griffin

This looks like a chic outfit one of my coworkers would stroll into the ELLE offices wearing—you know, the kind that makes you try a little harder the next day. Follow Kerry Washington’s lead and invest in a striped dress that adds dimension to your wardrobe.

Borrow From the Boys

rose in new york city

TheStewartofNY

More! Women! Wearing! Ties! I love to see it. And the zip-up hoodie? Now that’s a fashion trend I can really get behind. I’m inspired by every one of Rosé’s ensembles. This is just another flawless look to add to her ever-growing list.


Put Comfort First

new york, ny january 10 katie holmes is seen on january 10, 2025 in new york city photo by xnystar maxgc images

XNY/Star Max

Katie Holmes is an underrated, low-key style icon. Doesn’t this just prove it? A big, shearling-trimmed coat like Holmes’ is a tentpole item for cold-weather dressing. While comfortable sneakers are a must-have for getting around New York City.


Extend the Life of Seasonal Pieces

new york, new york february 11 olivia palermo wears black white dress with graphic print, bomber jacket, black turtleneck, boots outside jason wu on february 11, 2024 in new york city photo by christian vieriggetty images

Christian Vierig

Not every summer frock can be translated through the winter, but Olivia Palermo’s look is a masterclass in doing so. When layering a dress, opt for a turtleneck or tights underneath to stay warm.


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