Planning a trip to New York this winter and need ideas for what to wear? Check out this blog post for all my top New York Outfit Ideas Winter.
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Planning a weekend trip to NYC? Whether you’re flying in for a quick getaway or making the most of a short stay, you’ll need New York outfit ideas for winter that cover everything from the plane ride to a full day of exploring or even a Broadway show! Plus, packing light is always a challenge!
I recently packed for this exact scenario, flying in on Friday afternoon and seeing Wicked on Broadway, exploring all day Saturday, and heading home Sunday around lunchtime. My goal? Outfits that are stylish, comfortable, and versatile enough to mix and match—without overpacking. Here’s what I chose and how I made each outfit work.
New York Outfit Ideas Winter:
Friday: Travel and Broadway Night
For the flight, I want to be comfortable but still put together. I’m going with my J. Crew sweatsuit, sneakers that are easy to slip on and off at security and my main outerwear piece for the trip: my wool overcoat, which I’ll wear on the plane to save space in my luggage.
Friday night, we’re seeing Wicked on Broadway, so I wanted a look inspired by Elphaba and Cynthia’s interview outfits from the Wicked movie press tour. I started with a blue button-down with green beaded detailing from Loft, layering it under a dark green sweater. To add an extra Elphaba touch, I wanted to incorporate green tights. I first tried them with a pleated skirt but didn’t love the fit, then switched to a black skirt, which worked but didn’t feel quite warm or comfortable enough. Finally, I landed on black leather pants, letting the green tights peek through my shoes for the perfect balance of style and practicality.
For accessories, I added jade cuffs from Seree, a pearl threader earring from Heir Raleigh, and fake nails with a green and gold design as a nod to Cynthia’s. My Coach Rogue bag became the go-to for the trip since it seamlessly works for both daytime and evening. The biggest challenge was choosing shoes—I went back and forth between flats, sneakers, loafers, and boots before ultimately settling on flats.
Saturday: Exploring the City
Since we’ll be walking all day, I wanted something comfortable, warm, and stylish. I first tried a monochromatic cream look with an oversized herringbone blazer, cream Chelsea boots, and a burgundy scarf that matched the blazer’s accents, but it just didn’t feel quite right.
Next, I tried a J.Crew top I had bought in a moment of desperation, only to realize it looked nothing like it did on the model. It was a total miss—proof that impulse buying something just for an occasion rarely works out!
After some trial and error, I landed on a denim-on-denim look with a chambray button-down and lighter-wash jeans. I layered a black cardigan for warmth and added a blue scarf for a monochromatic touch. My Golden Goose sneakers will likely be my go-to shoes, and I’ll accessorize with earmuffs if needed.
I had no idea at the time, but this ended up being my engagement outfit! I went back and forth on what to wear for Saturday while packing and even asked my now-fiancé for his opinion—which slightly freaked him out because he thought I was onto him!
Sunday: Brunch and Travel Home
For Sunday, I need something that works for a sit-down brunch and the flight home. I decided on a cozy cashmere hoodie sweater paired with the relaxed baggy jeans I wore on Saturday, a neon yellow beanie and my Golden Goose sneakers.
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