Image Credit: Instagram / @kellyrutherford

Babe Wake Up, Kelly Rutherford (AKA Lily Van Der Woodsen) Just Posted Another Mirror Pic

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Dressing for the winter has never been my forté mostly because I’ve never reallyyyy had to do it. Yes, I know we New York City transplants are insufferable in many ways, but have you ever considered the fact that we’re just fucking cold?? As someone who only wants to leave my house if I’m in a capital L Look, it’s a lot easier to operate from April – October (or in my home state of Louisiana, but they have a whole other host of issues). This year, however, I will not be succumbing to the  jeans/sweater/black puffer jacket formula, and instead swapping it for a stylish, cozy winter outfit largely thanks to the Instagram of one of NYC’s elite and most iconic it girls, Lily Van Der Woodsen Kelly Rutherford.

After studying Kelly Rutherford’s style on Instagram where she blesses us with frequent elevator selfies, I’ve identified the key pieces in achieving her chic balance of femininity, utility, and classic rich mom style. The best part is, it’s all comfy as hell, which, if we’re being honest, is the only way my seasonal depression is letting me get dressed anyway.

Elevated Sweats

Kelly Rutherford posing in front of a winter mountain scene in a nice sweat set.
Image Credit: Instagram/@kellyrutherford

The best thing about Kelly’s style is that it takes the soft and cozy things you actually want to wear in the winter and makes them look like a legit outfit. Luckily this includes sweatpants – just go for an elevated set like these pants and hoodie from Gap that bring a little bit of texture to your look (and hides crumbs better than the classic cotton variety).

Gap CashSoft Shaker-Stitch Sweater Pants
 $63 (was $79.95)

CashSoft Shaker-Stitch Sweater Hoodie
 $63 (was $79.95)

Cozy Skirts

Kelly Rutherford taking a mirror selfie in an elevator mirror wearing a grey sweater and skirt
Image Credit: Instagram/@kellyrutherford

You know what’s always more comfortable than wearing pants? Not wearing pants. If you think that’s just not practical when temperatures drop, try pairing a cozy knit midi skirt (like this one from Everlane or this one from COS) with tights and boots or sneakers and your favorite sweater.

Everlane The Cozy-Stretch Skirt
 $39 (was $98)

Flared Merino Wool Maxi Skirt

Not Your Basic Black Puffer

Kelly Rutherford wearing a black puffer while taking a mirror selfie in an elevator

As annoying as it is, sometimes a practical puffer is your best option for braving the cold, but Kelly always goes for options with interesting proportions like this chic quilted jacket or duvet wrap vest to keep it out of “are you from New York even?” territory.

Straight Quilted Pattern Short Jacket

Gap Duvet Wrap Puffer Vest
 $59 (was $118)

Winter White

Kelly Rutherford wearing an all white outfit while taking an elevator selfie
Image Credit: Instagram/@kellyrutherford

Part of what keeps Kelly’s style from getting too stuffy is that she breaks a lot of traditional style rules like “don’t mix navy and black” or “no white pants after Labor Day.” (Both complete BS, for the record.) Don’t be afraid to bring your white jeans back out and pair them with a cozy knit and boots for the winter.

Baggy Dad Wide Lieg Women's Jeans

Old Money Outerwear

Kelly Rutherford wearing a leopard coat while taking a mirror selfie.
Image Credit: Instagram/@kellyrutherford

Trust me, I’m as tired of the old money, quiet luxury conversation as everyone else, but there’s really no other way to succinctly describe the coats in Kelly’s rotation. Vintage looking (faux) furs and cape coats that feel like estate sale scores are what make the rest of her chill essentials feel like a fashion statement.

Leopard Print Shawl Collar Faux Fur Coat
 $231.20 (was $298)

Wool Blend Cape
 $232 (was $290)

Practical Footwear

Kelly Rutherford in a mirror selfie in the elevator wearing winter boots
Image Credit: Instagram/@kellyrutherford

A dainty little heel or a super classic riding boot would just not have the same cool effect with Kelly’s aforementioned rich lady staples, and TFG because trying to trek around the city in them sounds like my worst nightmare. Bring your winter outfits back down to reality with a pair of sturdy hiking-inspired boots like these by Vince Camuto, this pair available on Amazon, or this black pair from Schutz that will go with literally everything.

Vince Camuto Women's Mertami Lace Up Bootie Combat Boot
 $44.99 (was $61.99)

The Drop Women's Caleb Shearling Hiking Boot

Kaile Leather Bootie
 $99 (was $198)

Elegant Accessories

Kelly Rutherford holding her dog in an elevator wearing sunglasses while taking a mirror selfie
Image Credit: Instagram/@kellyrutherford

To top it all off, Kelly keeps it clean and chic with elegant (but not boring) accessories. When all else fails, remind everyone that you still have style with a pair of ‘70s style sunnies, a bold cat eye, or a staple black bag with modern mixed metals.

1970s Vintage Style Hexagon Square Oversized Sunglasses

The Hepburn Sunglasses

Staud Ollie Zip Leather Shoulder Bag

Maddy Paul
Maddy Paul
Maddy Paul is a Senior Content Manager at Betches, a self-proclaimed professional shopper, certified yapper, and 2x marathoner (brag).