I'm 56, Live in NYC, and Love Wearing These Knitwear Outfits

We routinely turn to Elaine Davis's feed, @squarepearls, when we're on the hunt for effortless and chic style inspiration. Given that she resides in NYC, she's more or less an expert in crafting those outfits that are elevated yet easy for that on-the-go lifestyle. She also happens to be 56. And while age has nothing to do with what you should or shouldn't wear, her more experienced sartorial point of view is also particularly intriguing. With all that in mind, we thought we'd get in touch with her to uncover the specific knitwear outfits she's into at the moment. You know, to inspire those winter ensembles.
"Living in NYC, I get to dress for all four seasons, and my favorites are fall and winter," she told us. "There's nothing I love more than cozy knitwear that I can dress up or down." On that note, below you'll uncover six outfits featuring various knitwear silhouettes that Davis is loving, and that you might be interested in testing out as well. Keep scrolling for more—there's also a smattering of shopping picks sprinkled throughout.
"When I want a more elevated sweater look, I'll opt for an embellished cardigan with a matching skirt."
"My oversize cable-knit pullovers are staples in my wardrobe and are both classic and trendy."
"A knit dress is one of my go-to looks during the fall and winter months. I find them super easy to dress up or down by changing my footwear and accessories."
"I love how a pastel sweater pairs so beautifully with all my fall and winter neutrals."
"A long cardigan or 'coatigan' thrown over jeans and a tee pulls my casual weekend look all the way together."
"Comfy, chic and versatile is definitely a combination that I strive for in an outfit on a regular basis. I always keep a knit jumpsuit handy. It checks all the boxes."
Next, check out the dress trends Davis loves.

Bobby Schuessler is a fashion editor with over a decade of editorial experience covering shopping, style, and beauty. He's spent 10 years at Who What Wear, currently leading the market team to deliver highly covetable and convertible content. He creates data-driven shopping guides featuring top retailers like Nordstrom, Shopbop, and Net-a-Porter and is at the forefront of Who What Wear's shopping tentpole strategies, including Amazon Prime Day. He also works on branded content initiatives and appears on camera in video and shopping livestream franchises.
-
5 Street Style Trends From Milan Fashion Week That Will Be Everywhere This Fall
Take notes.
-
The Trick NYC Fashion People Are Using to Make "Boring" Jeans-and-Tee Outfits Look Chic This Fall
Jennifer Lawrence was spotted wearing it, proving just how well this styling hack works.
-
Laura Harrier Can't Stop Carrying This Timeless The Row Bag (and No, It's Not a Margaux)
One, two, three times in one week.
-
This Dated Denim Pairing Is Suddenly the Chicest Way to Wear Jeans for Fall 2025
Easy and stylish.
-
Everything Who What Wear Editors Saw, Wore, Did, and Ate During NYFW
Let's dive in, shall we?
-
Paris Hilton's World: Her Pink Motorola Razr, Favorite Y2K Looks, and What 11:11 Media Means to Her
A glimpse into the life of this savvy entrepreneur.
-
These 33 New Fall Zara Items Are Giving Off "I'm Chic Walking in a Metropolitan City" Energy
Cool, elevated, and forward pieces.
-
This Simple Fashion Person–Approved Layering Technique Changed the Way I Wear My Basics
Effortlessly cool.