Tessa Faye O’Connell is a contributor known for her work at various fashion houses, specializing in media and public relations, currently working at Coach as its global PR director. She’s a mom of two, working to expand her influence in the fashion space through styling while also just making it out the door on time.
Now that it’s winter, getting dressed to make it into the city for work has a fun new challenge: braving the cold while looking put-together. But voilà, I have sweaters. I’ve amassed quite a collection over the years, but as I’ve worked hard to ensure that everything in my wardrobe is something I love and can mix and match with other items I own, I’ve come to appreciate certain styles over others.
Every fall, as I plan for the months ahead, I take inventory of the pieces I have, shed what doesn’t work for me anymore, and make a list of what’s missing so that I always have one that works. The best thing about sweaters is that there are different styles to fit the mood—polished, laid-back, elevated, neutral, and a variety of prints that make getting dressed in the winter fun. Worn with jeans, trousers, skirts, or casual silk pants, there is something for everyone.
As of now, these are my favorites, but as the snow keeps coming, there may be new additions to add to the rotation.
The Cotton Sweater
(Image credit: Tessa Faye O’Connell)
A cotton sweater is lighter than wool or cashmere but extremely comfortable to throw on over a T-shirt and weather the day ahead. (Pun intended.) My current go-to is Honest Cotton’s white pullover, but there is a variety of neutral-tone cotton sweaters that can be everyday pieces.
Honest Cotton
Travel Sweater
perfectwhitetee
Janet Sweater
J.Crew
2025 Rollneck Sweater
La Ligne
Solid Marina Sweater
Jenni Kayne
Cotton Fisherman Sweater
The Cardigan
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I was against the cardigan for a long time until I realized the power of wearing a cardigan like a top. Unlike other sweaters that need to be layered, there is a certain type of cardigan that offers a polished look while keeping you warm in the office.
almina concept
Classic Crew Wool Cardigan
American Vintage
Cardigan
The V-Neck Sweater
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I swore off V-necks entirely until I realized all that was missing was a T-shirt layered underneath. It is the perfect item to feel cozy in or elevated in with the right trousers. I have lost count of the number of times I’ve thrown on this Jenni Kayne sweater to feel put-together.
Jenni Kayne
Flynn Cashmere Sweater
Leset
Jesse V Neck Pullover
ZARA
Soft Knit V-Neck Sweater
Naadam
Super Luxe Cashmere V-Neck Sweater
Sold Out
The Cashmere V-Neck
Everlane
The Classic V in Cashmere
The Fair Isle Sweater
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My favorite alter ego is the one where I am snowed in, in a cabin in the woods, so any way that I can incorporate a Fair Isle sweater into my wardrobe daily is a plus for me. Cozy and chic.
joe’s jeans
The Wells Fair Isle Sweater
The Great
The Nordic Sweater
Polo Ralph Lauren
Fair Isle Lace Up Sweater
A.L.C.
Ella Fairisle Merino Sweater
&Daughter
Fairisle Oversized Crewneck in Dark Natural Multi
The Brown Sweater
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A brown sweater, specifically with texture, always pulls through.
lauren manoogian
Askew Pullover
& Other Stories
Mohair Super Soft Hairy Knit Sweater
Buck Mason
Marled Trail Seastack Wool Tweed Crewneck
COS
Cashmere Crew-Neck Sweater
Madewell
Ribbed Cotton-Blend Sweater
The Striped Sweater
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When I want to make a statement without being over-the-top, stripes are my favorite to utilize. Whether it’s a cropped style or a button-down, they offer that little bit of something extra to pull the outfit together.
Jenni Kayne
Cooper Cardigan
Reformation
Cashmere Boyfriend Sweater
La Ligne
Mini Marin Sweater
alex mill
Taylor Striped Cardigan in Cotton Cashmere
The Plaid Sweater
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What’s better than a plaid shirt? A plaid cashmere shirt. Need I explain more?
guest in residence
Plaid Work Shirt
Vince
Checked Plaid Cashmere Polo Cardigan
White & Warren
Cashmere Luxe Button Down Shacket in Dark Umber Combo
The Elder Statesman
Plaid Big Shirt