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Ugg’s New Dipper Boot Is a Modern Spin on the Y2K-Beloved, Cold-Weather Classic

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Can you smell the pumpkin spice in the air? The first sign of the fall season — that autumnal breeze of crisp morning air before the leaves change color — serves as a reminder that it’s time to switch out those cute summer sandals for comfortable ankle booties. For fashionable Ugg fanatics, you already know it’s time to keep your eyes peeled for Ugg’s new silhouette of the season, one that will inevitably sell out by the time it reaches peak TikTok popularity. Let’s make sure you secure your comfy, cozy, cool booties and point your attention to the new Dipper Boots. 

The new Ugg Dipper boot made its debut during New York Fashion Week; not on the catwalk, but on the feet of style-influencing celebrities. On September 10th in New York City, Lori Harvey took a hot girl walk on a rainy, humid day, strutting down the street in the new Dipper booties, paired with a classic white tank top (tied in the back to show some bare midriff) and a rich, purple-hued cargo micro-mini skirt by The Attico. This past Friday, Emily Ratajkowski paired her Ugg Dipper boots with a red knit midi skirt (hanging low on the hips) and cropped layers, topped off with a black suede jacket. Both Harvey and Ratajkowski — like many Hollywood starlets who donned the classic booties decades before them — balanced chunky Ugg boots with skin-baring ensembles. Love it or hate it, the Y2K outfit formula showcases the appeal of cozy Ugg booties for both warmer and colder climates. 

Over the weekend, rapper Cardi B signaled the official start of Ugg season to her fans, too, showing off her new booties in a brand-sponsored Instagram post with green cargo pants cinched just above the ankle to show the Dipper’s slim leg design. 

The Ugg Classic Dipper boot’s design was a wise choice for the beloved bootie and slipper brand. The new release plays into the leg-baring, sock-showcasing outfit equation that has quickly become one of today’s most popular fashion statements. Trendsetting fashion darlings like Hailey Bieber have been sporting chunky lug-sole women’s loafers with dress socks all summer long; the new Dipper boot creates a similar effect with a neoprene upper that retains its shape and hugs the ankles for a perfect proportion play with a contrast to the wider lower part of the bootie that houses the cozy UGGplush lining you know and love. The new upper design provides a solution to the Classic Short style dilemma of pant bunching and creasing (unless you were one of the many fashionistas in the early aughts who proudly donned tapered skinny jeans). Whether you opt for the leggy look or throw on your baggy denim bestie, the new Ugg Dipper boot is made for endless fall outfit opportunities. 

Last fall, Ugg introduced the Classic Ultra Mini Platforms. Before a press release could hit our inbox, Gigi Hadid and Elsa Hosk were already snapped by paparazzi donning the elevated classic Ugg boot (literally; the boot was given a thicker platform sole that made the “Sad Autumn Girls” beam with delight). Most of these booties sold out almost instantaneously, leaving many Ugg lovers with an incomplete fall footwear rotation until early 2023. 

This fall, don’t hold out on purchasing the new Ugg Classic Dipper, or you might have to wait until after the holiday season. Currently, both Chestnut and Black colorways are available in all sizes, so before you swap your seasonal wardrobes for sweater weather, take a moment to secure this new release. Once temperatures start to dip, so will the inventory of these chic women’s winter boots.  

Ugg Classic Dipper Boots
Size range: 5 to 12
Colorways: Chestnut, Black

Meet the Author

Adam Mansuroglu is the Director of Commerce for Footwear News and WWD, overseeing strategy for shopping content on both brands, along with writing and editing shopping guides, product reviews, and shopping trend stories for all types of footwear, from designer shoes to athletic sneakers for both men and women. Prior to his current role, Mansuroglu was a fashion editor and stylist at Cosmopolitan Magazine, Style Editor at BestProducts.com, and Senior Style & Gear Editor for Men’s Health Magazine, where he edited the annual Men’s Health Sneaker Awards. Mansuroglu has been tapped as a shopping expert for editorial websites such as Wirecutter, and his writing has also appeared in Out Magazine, Esquire and other publications. Mansuroglu is a fan of Ugg winter slippers, and last fall purchased the Classic Mini Platform boot in red.

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