I've Lived in NYC and Boston—Here's Everything I Think Is Chic for Winter

Whether strolling the streets of Boston or New York City, there are some definite overlaps in what I reach for during the winter months. I don't know if I'd fully attribute that to the likes of each city, since I am a creature of habit no matter where I reside, but the options are chic nonetheless. My aim is to always look timeless and put together no matter what city I'm in.
This season, there are some key pieces I have been wearing on heavy rotation. Each is effortless and packs an elevated punch, including classic sweaters, dark-wash jeans, black booties, and more. Keep scrolling to check out six chic winter picks that have my attention right now.
Oversize Coats
An oversize coat instantly elevates any outfit. I like to reach for black, gray, and neutral options in a variety of timeless styles.
Camel Pieces
Any time I wear a camel piece, I receive a compliment. The timeless color gives ensembles an expensive feel.
Dark-Wash Jeans
When colder weather comes around, I find myself reaching for dark-wash denim styles. They feel dressier and more elegant. Plus, they go great with any top style.
Black Booties
I am loyal to versatile black booties, especially in comfortable flat and low-heel versions. I keep the higher styles for more formal occasions.
Classic Sweaters
How I love sweater season. There is nothing I appreciate more in fashion than a classic sweater to cozy up in. Crewnecks and turtlenecks are usually my top picks.
Woven Bags
No matter the season, a chic woven leather bag is a great idea, but there is something about adding the beautiful textured detail to a winter look.

Jennifer Camp Forbes is a senior shopping editor at Who What Wear, where she has worked in a variety of capacities including creative director and various editor roles. She’s a well-known shopping expert that’s sought out for advice and insight on the latest trends, outfit ideas, and fashion picks thanks to her thoughtful shopping roundups. Jennifer's lifelong interest in fashion led her to intern at Harper’s Bazaar as an undergraduate. Later, while working towards her masters degree in psychological counseling at Columbia University, she founded two digital fashion publications: Le Fashion and Olsens Anonymous. The popularity of both sites grew and after graduation she decided put her plans to become a therapist aside to pursue a career in fashion.
-
I Just Saved $1200 By Shopping This Viral COS Sweater Instead of Its Designer Reference
Girl math.
-
Listen, Being Cool in 2025 Requires Just Two Things: Loose Jeans and This “Weird” Viral Flat-Shoe Trend
They're strange, but so chic.
-
The No-Fuss Outfit Chloë Sevigny Wears When She Wants to Look Cool in NYC Without Trying
It's surprisingly chic.
-
My Mom Is in Her 50s and Asked Me for Fashion Advice—8 Chic Nordstrom Outfits I Put Together for Her Under $425
Outdated prints and "ugly" shoes included.
-
I'm Buying My Cold-Weather Basics From Gap, J.Crew, and Banana Republic—Here's What's in My Cart
Stocking up on layers.
-
These Easy Outfit Formulas Make Even Fall's Most Polarizing Boot Trend Look Cool
See the inspiration inside.
-
Sophisticated Women in Paris, New York, and London Will Be Wearing These Luxury Items All Winter
Only speaking facts.
-
Fashionphile's Done the Research: These Are the It Bags of 2025
The 2025 Resale Report is here.