Nicky Hilton’s Winter Street Style: How She Styles Prada Boots & Nike SB Dunks

During two outings in New York City in January 2021, Nicky Hilton demonstrated two very different approaches to winter dressing.

One look leaned into polished biker-inspired tailoring with rugged Prada boots, while the other paired a statement leopard-print coat with classic Nike SB Dunk High sneakers for a more relaxed take on cold-weather style.

Together, the outfits show how Hilton balances luxury investment pieces with practical footwear, making each look feel wearable long after the trends of the moment have passed.

Look 1: Prada Brixxen Boots Elevate a Monochrome Biker Look

Nicky Hilton steps out in Manhattan wearing a Muubaa shearling biker jacket, a Monse x Playboy sweater, skinny black jeans, Prada Brixxen boots, and a Valentino Garavani Roman Stud shoulder bag on January 19, 2021 (Credit: Instar / WENN)

Wearing a black-and-white outfit, Nicky bundled up in a black leather biker jacket with a shearling collar from London-based luxurious leather fashion brand Muubaa.

Underneath her tough-chic outerwear, Nicky wore a white merino wool knit sweater featuring the iconic Playboy Bunny logo on the front.

Her relaxed top, which also has a ribbed neckline, is from Monse and Playboy’s Pre-Fall 2020 collaboration. Showcasing her long, slender legs, the hotel heiress teamed the look with a pair of skinny black jeans.

Nicky Hilton demonstrates her signature high-low approach to winter dressing by pairing rugged Prada Brixxen combat boots with a luxe Valentino Roman Stud bag and a Monse x Playboy knit

Accessories echoed the tough-luxe feel of the outfit. Nicky carried Valentino Garavani’s quilted Roman Stud shoulder bag, whose oversized pyramid studs added texture without overwhelming the monochrome palette.

Beauty-wise, Nicky slicked her hair back and highlighted her eyes with smoky eyeshadow and a winged feline flick.

A close-up highlights Nicky Hilton’s slicked-back hairstyle, smoky eye makeup, and Monse x Playboy sweater layered beneath her black shearling-collar Muubaa biker jacket

The outfit was grounded by a pair of Prada Brixxen booties, whose chunky lug sole and shearling lining complemented the leather jacket while adding practical traction for winter streets.

Later that year, she wore the same boots with a brown Moncler jacket, a midi tote bag from Edinburgh-based luxury brand Strathberry, and Illesteva Donna sunglasses.

Nicky Hilton grounds her monochrome winter outfit with Prada’s shearling-lined Brixxen leather lace-up boots, featuring the house’s signature enameled triangle logo and chunky lug soles

Her Prada boots also have metal hooks and eyelets, Prada’s enameled triangle logo, and about 1 inch of lug rubber outsoles.

Emblematic of the brand and reinterpreted in always new ways, the enameled metal triangle logo decorates these Brixxen laced booties, lined with shearling and completed by a rubber sole

While her first look embraced an all-black, biker-inspired palette, another New York outing showed a softer side of her winter wardrobe built around animal print and sneakers.

Look 2: Nike SB Dunk High Sneakers Balance a Bold Leopard Coat

For her second winter look, Nicky built the outfit around an Apparis leopard-print faux-fur coat, proving that one statement outerwear piece can carry an otherwise understated wardrobe.

Nicky Hilton pairs an Apparis leopard-print faux-fur coat with black-and-white Nike SB Dunk High sneakers, proving statement outerwear works just as well with classic skate shoes as it does with boots on January 13, 2021 in New York City

Rather than matching the dramatic coat with heels or boots, she opted for Nike SB Dunk High sneakers. The classic black-and-white colorway kept the outfit grounded while giving the polished coat a more effortless street-style feel.

Originally released in 2012, the black-and-white Nike SB Dunk High remains one of the silhouette’s most versatile colorways.

Rather than disappearing after its initial run, the model has continued to circulate on the resale market, with StockX listing hundreds of Nike SB Dunk High variations as of August 2026, from general releases to sought-after collaborations.

The clean black-and-white palette, suede-and-leather construction, and skate-inspired design help explain why this classic colorway still pairs effortlessly with everything from statement outerwear to everyday denim.

A close-up of Nicky Hilton’s black-and-white Nike SB Dunk High sneakers highlights the timeless colorway that continues to pair effortlessly with everything from denim to bold winter coats

She completed the outfit with her Valentino Roman Stud bag, red Le Specs x Adam Selman cat-eye sunglasses, and a black face mask, tying together sporty sneakers with polished designer accessories.

Nicky Hilton finishes her winter street-style look with an Apparis leopard-print coat, a Valentino Garavani Roman Stud shoulder bag, and red Le Specs x Adam Selman cat-eye sunglasses for a polished mix of classic and playful accessories

More of Nicky Hilton’s Timeless Designer Shoe Style

Whether she’s pairing rugged Prada boots with a shearling biker jacket or dressing down a bold leopard-print coat with classic Nike SB Dunks, Nicky Hilton consistently favors well-made shoes that outlast seasonal trends. Explore more of her standout designer footwear and fashion moments below.