How To Wear A Sweater

A tiny guide to practical/delightful knitwear nirvana. Plus: We're giving away 3 pairs of the chicest/warmest socks ever.

I can’t remember when it was exactly. But I do remember how I felt when I opened up a storage bag from the “off-season” section of my closet to discover that one of my expensive cashmere sweaters had unwittingly become a nightclub for moths. Holding it up to inspect the damage, tiny chunks of pricey knitwear sprinkled out onto the floor like clumpy confetti. The sweater was no longer a sweater but something more like a ratty post-apocalyptic scarf on Dune.

And yet…I was elated. Having a “great” sweater taken from me by the moth Gods—a sweater I thought I loved but never quite vibed with—felt like an act of serendipity. A happy accident. Inconspicuously dumped by the sweater I secretly hated anyway. To describe my feelings/attitude about good sweaters as conflicted is merely scratching the surface. (Scratching being a key word here.)

I’ve grown up hating sweaters. How they feel. How they fit. I remember once seeing my dear friend Laura running across a field upstate wearing a long chunky cable-knit cardigan belted around her waist. It was late fall and her long dark hair was swinging down her back. She looked impossibly beautiful, and yet all I could think in that moment was, hmmmmmm, I wonder if that sweater is itchy?

Regal. And also warm. Sweater Donna Wilson…I can attest, it does not itch.

When I was little, it wasn’t uncommon to open up our front door on Long Island in wintertime and be greeted by three feet of snow. As a child, so much snow makes wearing a scratchy sweater almost bearable. But in the absence of all that frequent cold and inclement frosty weather lately, how does a lifelong sweater-phobe reconcile herself with winter’s most beloved fashion garment?

The truth is, I love the way a good sweater looks…cozy and personal, like something you’ve had for a while that just keeps getting better with age. But despite the familiar Holiday vibes, it’s easy to make excuses for bad sweaters we choose to keep because we think we’re supposed to. Because it’s winter and, God forbid, how can we not have any warm sweaters in our closet? Having been forced to wear truly gorgeous shetland sweaters growing up that felt something like rolling around naked in breadcrumbs…I’ve learned my lesson. If a sweater is itchy or ill-fitting, it is immediately OUT. (And now as a mother, if my daughter tells me anything is even remotely itchy, it’s relegated to the hand-me-down pile, stat. )

Mood. Courtesy of Lou and TVU, when I’m wearing sweaters lately…

Whenever I have historically worn a sweater, the sweater has seemingly plotted to wear me. Despite wanting to look festive and chic, my dominant thought is simply: I Am Wearing a Sweater. And because I like living my life with ease and flexibility, I avoid sweaters like the plague.

Hence, over the past few years, I have curated a small collection of Perfect Sweaters…knits that, after a lot of trial and error, tick the critical CB Sweater Boxes:

🎯 Does not itch.

🎯 Does not make me sweat or make my shoulders or elbow pits cry out in protest.

🎯 Does not have a weird waist band that implies I have two waists as opposed to one.

🎯 Does not make me look like I am a relative newcomer to wearing clothes.

I mean, after all of this, even finding a sweater that feels good AND looks good AND keeps you warm in cold weather is its own kind of holy grail. But the truth is after snooping around a LOT—both on the interweb and in my own closet—I found a few very, very good ones. As well as some pleasingly refreshing ways to wear them.

So, what’s the secret—to wearing a fantastic sweater in a stylish and also humane way? Before we get into it, our friends over at Eleven Six—makers of the most gorgeous ethical knit sweaters, LOVE what we’re doing here, and are giving away a 3-pack of their signature alpaca-wool blend socks to one lucky ATA subscriber.

All you have to do is drop a comment below if you want to put your name in the running. And, if you’re not already a Paid subscriber, now would be the perfect time to upgrade…we’ll have a handful more treasures to gift you leading up to the New Year—including THREE gifted Mansur Gavriel bags!—so, come join us.

Okay now, let’s get into it ❤️…

Some brief inspiration—Life In Sweaters.

Clockwise, from top left: Ellsworth Kelly sketching at the beach (those BOOTS!); Becky Malinsky making a very good case for Polo sweaters; Andy Warhol at his NYC studio in the '80s; The Row; a woman I spotted crossing the street in SoHo wearing a sweater in an easy way I wish I could; TIBI

The cardigan that feels like your favorite blazer…