Oprah’s Peak Cozy Outfit Includes the One Shoe Trend That’s a No-Brainer for Winter

She made an incredibly stylish return to the Big Apple.

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Oprah
Oprah. Photo:

Splash News

When Oprah talks, I listen! Whatever Oprah wears, I wear! Long story short, she’s my eternal muse and my inspiration for so many things — her Favorite Things list is like a holy grail that I turn to whenever I need any sort of inspiration — and that’s exactly why I’m copying her latest ‘fit when I finally leave my house later today. 

Oprah was photographed out in New York City on January 19, the first time she’s been back in the Big Apple since the pandemic, and though she’s a West Coaster, she knew exactly what the East Coast weather called for: cozy from head to toe, don’t you know? It’s her M.O. after all, and frankly, the vibe that most people are going for in the depths of winter, which is why I think everyone (not just me) will be fond of her city-going ensemble.

The media mogul went with a monochrome look that struck the perfect balance between staying comfortable while still feeling elevated. How did she do this, you ask? Well, said elevation was achieved by sticking to one color from head-to-toe — and we know a monochrome look has the power to look really expensive when done right, and Oprah’s did it right, opting for an oversized sweater, a coordinating poncho, comfy pants (possibly fancy sweats?), and beige Chelsea boots, which are basically a requirement this time of year. 

I know, I know: You’re probably thinking that boots are an obvious pick this time of year. But I’m not talking about any regular ol’ boots: I’m talking about Chelsea boots, specifically, the simple, sleek ankle style that’s like the bootie equivalent of white sneakers. As in, they pair with everything and really require very little thought to wear. Oprah’s pair features a slightly chunky sole, a trendier touch, but the silhouette also comes with more toned-down bases, which means there’s a Chelsea boot for everyone. Pinky promise. 

Oprah wore her cozy pants over the boots, but you can easily tuck skinnies into them, too. All that to say, this shoe style is extremely versatile and officially Oprah-approved, which means one thing: I’m buying myself a new pair. Shop some of the coolest Chelsea boots below.

Get the Look: 

Open Edit Mya Lug-Sole Chelsea Boot
Shop now:
$45 (Originally $100); nordstrom.com

Cougar Shani Waterproof Chelsea Boot
Shop now:
$160; nordstrom.com

Calvin Klein Remola Lug Chelsea Boot
Shop now:
$83 (Originally $139); nordstrom.com

Mia Lenia Platform Chelsea Boot
Shop now:
$48 (Originally $80); nordstrom.com

Camper Milah Chelsea Boot
Shop now:
$157–$180 (Originally $225); nordstrom.com

Calvin Klein Anissa Faux Shearling Chelsea Bootie
Shop now:
$125 (Originally $179); nordstrom.com

Farm Rio Lug-Sole Chelsea Boot
Shop now:
$163 (Originally $250); nordstrom.com

Steve Madden Hayle Platform Chelsea Boot
Shop now:
$100–$110; nordstrom.com

Bernardo Briton Chelsea Rain Boot
Shop now:
$165; nordstrom.com

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