Kendall Jenner Reveals the Best Winter Shoes to Elevate Your Comfy-Cozy Holiday Outfits

Sweatpants have never looked so sleek.

Kendall Jenner elevated her comfy-cozy crewneck and sweatpants with red ballet flats
(Image credit: Backgrid)

Curating a set of comfy-cozies isn't as effortless as it seems. Just throwing on a matching two-piece is simple in theory, but what happens if you need to leave the house? Enter Kendall Jenner's pre-Christmas combination: the ballet flats-focused solution that elevates even the most laid-back holiday outfits.

On December 17, Jenner's understated, yet festive outfit streak arrived on Melrose Ave in West Hollywood. Her first layers? A white T-shirt beneath a cashmere crewneck. She coupled the '90s duo with wide-leg, sweatpant-ish pants. They're her most relaxed bottoms of the season, beating dark-wash jeans, the stirrup leggings trend, and even yoga pants.

She typically styles a look like this with The Row's City Flip-Flops, but the leather thongs weren't nearly festive enough for December. So, they traded places with crimson red ballet flats. The $890 flats also boasted The Row tags. While Jenner hasn't worn this pair before, the lambskin leather, square toe boxes, and rubber soles looked perfectly worn-in. Knowing Jenner, she'll get her money's worth on the ruby shoes at a holiday get-together or two.

Kendall Jenner elevated her comfy-cozy crewneck and sweatpants with red ballet flats

Kendall Jenner dressed up black-and-white loungewear with poised The Row flats.

(Image credit: Backgrid)

Even a no-fuss lunch required a rare The Row bag, of which Jenner's closet offers no shortage. The model transferred all of her essentials from the Dalia to a slightly more spacious shoulder tote, topped in burgundy alligator. It features the same zipper-less closure and expandable sidewalls as the Marlo 17, which Jenner already owns in black and green. The exact price remains a mystery, but judging by Jennifer Lawrence's $33,000 The Row alligator Lady Bag, it's somewhere in the five-figure range.

If Jenner could constantly live in knitwear sets, flats, and an investment bag from The Row, I suspect she wouldn't protest. A few months ago, her ballet flats traded places with the slipper trend, in a similar shade of red. She hasn't worn those Milla Satin Flats by The Row since August—but with Hailey Bieber's recent slipper endorsement, there's no better time to un-retire them. Plus, the $890 slides would complement Jenner's black-and-white loungewear with ease.

Shop Outfits Inspired by Kendall Jenner

Meguire Hennes
Staff Writer, Fashion

Meguire Hennes is the fashion staff writer at Marie Claire, where she breaks down the celebrity looks living rent-free in her head (and yours). Whether a star is walking the red carpet or posing on Instagram, Meguire will tell you who they're wearing and why. When she's not gushing about A-listers from J.Law to Rihanna, Meguire also covers breaking industry news.

Previously, Meguire was the fashion news writer at The Zoe Report. She received a bachelor's degree in fashion studies at Montclair State University, and has freelanced at Bustle, Women's Health, Well+Good, and more. You can find her words across the fashion, beauty, health, and wellness verticals, because her Libra moon wouldn't let her settle on one beat. Follow her on Instagram for BTS moments from her Marie Claire era.