Welcome to "Who Won Fashion Today," where we award the boldest, best dressed person of the day. Winning fashion doesn't necessarily mean you're wearing the most expensive, trendiest, or prettiest dress. Rather, we reward risk-takers—those that stay true to their personal style and make us go, "Now THAT is a LEWK.”

By Ruthie Friedlander
Updated Dec 23, 2016 @ 10:45 am
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Credit: AKM-GSI

Whatever you are celebrating this season, don’t forget to celebrate Kris Jenner, because this outfit is a holiday miracle.

Let’s talk details: She’s wearing red Timberland boots, which is about the second chicest thing I’ve ever seen (the first would be white Timberland boots, right?). She’s wearing a full on red hooded onesie and looks even more at home in it than Cara Delevingne would. And then, there’s the bag. THE BAG. It’s THE bag. It’s the Gucci Dionysus Bamboo paneled leather tote ($3,500; neimanmarcus.com which is the most perfect thing because it’s (1) totally Christmas-y (2) trendy and classic at the same time and (3) Gucci (and that’s a reason alone in and of itself to want it). And the coat? Well, that’s just the icing on the cake.

Happy holidays, Kris. You win. Celebrities Obsessed with Their Timberland Boots

Credit: X17online.com

Image zoom Khloé Kardashian

The Good American co-founder arrived at the airport in black Timberland boots (shop a similar style here) and a matching top and LAZYPANTS ($20; saks.com). Kardashian added an eclectic splash of color to the travel-ready look with a camo jacket and Louis Vuiton patterned backpack. X17online.com

Image zoom Jennifer Lopez

The famed multi-hyphenate coordinated in cozy shades of oatmeal, stepping out in drop-crotch LAZYPANTS ($20; saks.com), a pocket tee, a comfy sweater, and a pair of Timberland Mayliss boots ($71; amazon.com). Splash News

Image zoom Josephine Skriver

Skriver lived her best life at Coachella in a black lace bodysuit, leather shorts, and a pair of nubuck lace-up Timberland boots ($140; zappos.com). She even demoed the festival-way of wearing the shoes, leaving the laces loose and pairing them with a high pair of black socks. josephineskriver/Instagram

Image zoom Josephine Skriver

For a Victoria's Secret event, the model swapped out her brown boots for a mint pair of Timberland boots, which matched her lacy bra top. victoriassecret/Instagram

Image zoom Joan Smalls

The model rocked a pair of six-inch white Timbs ($170; footlocker.com) for her day in the desert, pairing the unexpected footwear with white jean shorts and a denim vest. joansmalls/Instagram

Image zoom Serayah McNeill

The Empire star also got in on the trend at Coachella, pairing her denim overalls and yellow halter crop top with a pair of light gray Timberland boots ($170; nordstrom.com). serayah/Instagram

Image zoom Hailey Baldwin

The young model took to Instagram this week to show off her spring-y Timberland boots (shop a similar pair here) while sprinting her way to Coachella. haileybaldwin/Instagram

Image zoom Julianne Moore

The Oscar winner's Timberland boots ($165; zappos.com) were the perfect finishing touch to her black-on-black ensemble. Splash News

Image zoom Pharrell Williams

The music legend stepped out in Beverly Hills wearing a trendy pair of sand-colored Tim's (shop a similar pair here). Kevin Winter/Getty Images

Image zoom Bella Thorne

The young star posed is a set of undone classic Tims ($170; www.nordstrom.com). bellathorne/Instagram

Image zoom Drake

The "Hotline Bling" singer stepped out in London wearing a pair of black Timberland boots ($190; www.nordstrom.com). Ricky Vigil/GC Images

Image zoom Elle Fanning

The 18-year-old actress strolled through LAX in a set of heeled Timberland booties ($130; www.nordstrom.com) and nerdy-chic glasses. starzfly/Bauergriffin.com

Image zoom Nick Cannon

The father of two visited the set of Extra in a pair of classic Timberland work boots ($190; www.nordstrom.com). D Dipasupil/Getty Images

Image zoom Mark Wahlberg

The Ted star sported a set of Timberland work boots ($190; www.nordstrom.com) while on photocall in Rome. Ernesto Ruscio/Getty Images

Image zoom Kris Jenner

The famed matriarch looked red hot in a festive onesie and matching Timberlands (shop a similar style here: $170; www.nordstrom.com). AKM-GSI

Image zoom Jennifer Lopez

The singer stepped out in Beverly Hills on Thursday in casual dress and a set of monogrammed Timberland boots ($170; www.nordstrom.com). AKM GSI

Image zoom Gwen Stefani

There's no doubt about it, Miss Stefani is slaying the street-style game in her bright red Timberland boots (shop a similar style here: $170; www.nordstrom.com). Chinchilla/Bauer-Griffin/GC Images

Image zoom Rihanna

RiRi is also a fan of the dark brown Timberland boot (similar style: $114; www.nordstrom.com). NCP/Star Max/GC Images

Image zoom Gigi Hadid

The model stepped out in Aspen wearing a leopard-print coat and a set of winter-ready Timberland boots ($170; www.nordstrom.com). FameFlynet/AKM-GSI

Image zoom Cara Delevingne

These classic Timberland boots are the model's go-to for casual outings ($170; www.nordstrom.com). NCP/Star Max/GC Images

Image zoom Dakota Johnson

The Fifty Shades star braved the snow in a set of timeless Timberland boots (in black: $170; www.nordstrom.com). FameFlynet/AKM-GSI

Image zoom KANYE WEST

Kanye couldn't be Kanye without a tan set of Timberland work boots ($190; www.nordstrom.com). Bauer-Griffin/GC Images

Image zoom Rihanna

Rihanna does everything in her tan Timberlands—including perform ($170; www.nordstrom.com). Jon Furniss/WireImage

Image zoom Jake Gyllenhaal

The actor stepped out in N.Y.C. rocking a pair of dark brown Timberland boots (in gray: $190; macys.com) and a Canada Goose coat ($925; www.nordstrom.com). Luis Yllanes/Splash News

Image zoom Lily Donaldson

The model went back to black, pairing her festive LBD with fishnet stockings and a set of Timberland boots ($170; zappos.com). David M. Benett/Getty

Image zoom Fifth Harmony

The girl group paired denim ensembles with high-heel Timberland boots ($130; macys.com) during a performance on Britain's Got Talent. Splash News 1 of 26 Advertisement