8 Times Olivia Palermo Proved Investment Designer Shoes Outlast Seasonal Trends

Throughout January and February 2021, Olivia Palermo was photographed across Brooklyn and Manhattan wearing a series of winter outfits that reveal a consistent approach to cold-weather dressing: statement outerwear anchored by practical designer footwear.

Whether she chose combat boots, over-the-knee styles, loafers, or colorful pumps, the shoes remained the element that tied each look together.

The appearances, photographed during New York City’s snowy winter, show why Palermo’s footwear choices still hold up: most were not trend-only pieces, but polished versions of practical winter staples that luxury brands continue to revisit. Below, take a closer look at each outfit, the designer shoes she wore, and why these combinations still feel wearable years later.

Gianvito Rossi “Martis” Combat Boots Ground Olivia Palermo’s Colorful Cara Mila Coat

On February 15, 2021, Olivia Palermo and her husband, Johannes Huebl, stepped out in Downtown Brooklyn wearing coordinated winter layers that balanced practicality with luxury. While both embraced cold-weather tailoring, Palermo’s footwear drew the most attention.

Styled with a colorful Cara Mila coat and cropped checkered trousers, she finished the look with beige Gianvito Rossi “Martis” patent combat boots. The lug-soled design offered a polished alternative to traditional snow boots, making them the defining piece of an outfit that continues to feel relevant beyond a single season.

Olivia Palermo anchors a vivid Cara Mila leopard coat and pink turtleneck with beige Gianvito Rossi “Martis” patent combat boots while walking with Johannes Huebl in Downtown Brooklyn on February 15, 2021 (Credit: Instar / WENN)

Johannes Huebl echoed the practical mood of the outing in a tan overcoat layered over a gray knit sweater and black joggers. Brown suede loafers and a knit beanie kept the look relaxed while complementing Palermo’s more fashion-forward styling.

Johannes Huebl complements Olivia Palermo’s statement winter look in a camel double-breasted overcoat layered over a charcoal knit and gray scarf

Palermo built the outfit around contrasting textures, pairing a chunky pink turtleneck with Cara Mila’s “Bianca” leopard-print mink coat and grounding the bold outerwear with neutral Gianvito Rossi patent combat boots.

Olivia Palermo wears a Cara Mila leopard mink coat over a chunky pink knit sweater

She teamed the look with cropped checkered pants and slipped into a pair of Gianvito Rossi patent lace-up ankle boots.

Olivia has worn the label’s rugged “Martis” silhouette on several occasions, while she later styled the knee-high version during Paris Fashion Week.

The combat-inspired design has also been embraced by Olivia Culpo and Alessandra Ambrosio, highlighting the versatility of the Martis line.

A close-up of Olivia Palermo’s beige Gianvito Rossi “Martis” patent combat boots highlights their glossy finish, ribbed stretch panels, lace-up front, and chunky lug soles beneath cropped checkered trousers

Her mousse beige “Martis” boots combine glossy patent leather with stretch fabric and feature ribbed ankle panels, rear pull tabs, lace-up fastenings, 0.75-inch block heels, and chunky rubber lug soles that balance everyday practicality with the refined aesthetic Gianvito Rossi is known for.

Gianvito Rossi’s “Martis” boots in mousse beige patent leather combine polished patent uppers with ribbed knit panels and chunky lug soles

With her hair pulled back, Olivia revealed her gold-tone star-shaped stud earrings. She also accessorized with tortoiseshell-framed sunglasses and a face mask.

Olivia Palermo keeps a low profile with sunglasses and a face mask

Just a few days earlier, Palermo approached winter dressing differently, building the outfit around oversized outerwear before finishing it with chunky Italian boots designed for slippery city streets.

Fratelli Rossetti Lug-Sole Boots Make Her Moncler x Simone Rocha Coat Snow-Ready

The socialite kept warm in a long-line padded black coat with frilly trims and rosette detailing from the Moncler Genius and Simone Rocha collaboration.

Olivia Palermo layers a Moncler Genius x Simone Rocha padded coat over textured knitwear, finishing the snow-ready look with glossy Fratelli Rossetti patent lace-up boots while walking through New York City during a February 12, 2021, snowstorm

She wore her topper over a short vinyl jacket with a thick knit-lined collar and a chunky cream knit sweater underneath. To keep the cold out, she added a LeScarf red-and-black checkered scarf as a base layer around her neck.

Olivia Palermo bundles up in a Moncler Genius x Simone Rocha coat, a vinyl jacket, and a cream knit sweater

Olivia slipped into a pair of skintight leather pants and finished off her winter-chic outfit with chunky lace-up ankle boots from Italian luxury shoe brand Fratelli Rossetti.

Made from patent leather, these fashionable snow-ready boots feature contrasting laces, gold-tone eyelets, pull tabs, and chunky rubber soles.

A close-up of Olivia Palermo’s glossy Fratelli Rossetti patent leather ankle boots showcases their chunky lug soles, contrasting hiking-style laces, gold-tone eyelets, and rugged silhouette paired with sleek leather leggings

Keeping a low-profile, Olivia pulled her tresses away from her face. She accessorized with black sunglasses and a face mask.

Olivia Palermo scrapes her hair back and accessorizes with tortoiseshell sunnies and a black face mask

Earlier that month, Palermo demonstrated how streamlined footwear can keep an eye-catching coat from overwhelming an outfit.

Gianvito Rossi “Marsden” Over-the-Knee Boots Balance a Zebra-Striped Pologeorgis Coat

On a snowy afternoon in Manhattan on February 3, 2021, Olivia Palermo was spotted navigating the city streets in a monochromatic ensemble that prioritized texture and utility.

Known for her ability to balance high-end luxury with practical city-walking gear, she stepped out solo without her husband Johannes Huebl.

Olivia Palermo steps out solo in Downtown Manhattan on February 3, 2021, grounding her statement zebra-striped coat with sleek black over-the-knee leather boots that cut through the snow with polished ease (Credit: WENN / Instar)

The focal point of the look was a zebra-striped mink coat by Pologeorgis, a New York-based label. The striking pattern served as a contrast to the city’s industrial, wintry backdrop.

Her zebra mink fur coat ($3,500) features a lapel collar, hook-and-eye closures, slit pockets, and silk lining. Underneath her wild topper, Olivia wore a white long-sleeved blouse with a buttoned raised collar and an asymmetrical ruffled hem.

Olivia Palermo stays cozy in a Pologeorgis zebra-striped mink fur coat, white ruffled top, and leggings

She kept a low profile as she tied her hair up in a casual bun and hid her eyes behind a pair of oversized Le Specs sunglasses.

The daughter of real-estate developer Douglas E. Palermo also accessorized with simple stud earrings and stayed safe with a black face mask.

Olivia Palermo keeps things low-key with a casual bun, oversized sunglasses, and a black face mask

Walking over a snow pile, Olivia completed her winter outfit with black leggings and Gianvito Rossi Marsden leather boots, which you could buy on Mytheresa.

Olivia Palermo walks over a snow pile in Gianvito Rossi over-the-knee leather boots

These modernly designed over-the-knee boots are crafted from lamb leather and feature directional front zips set on 2-inch chunky ridged rubber platform heels. The shaft is about 23 inches high, while the leg width is 12.5 inches.

Olivia Palermo’s Gianvito Rossi Marsden boots feature a zip fastening along the center front

Gianvito Rossi’s black leather Marsden over-the-knee boots are set on chunky, ridged rubber soles

On another Brooklyn outing with Johannes Huebl, she swapped boots entirely, showing that loafers can work in winter when paired thoughtfully with heavier outerwear.

Santoni Double-Monk Loafers Bring a Tailored Twist to Her Leopard Winter Coat

Turning the streets of Dumbo, Brooklyn, into their own runway, the power couple bundled up in thick but chic contrasting winter outfits.

Olivia Palermo pairs a leopard-print Cara Mila coat with rolled-cuff jeans, mustard socks, and chunky Santoni double-monk loafers while out for lunch with Johannes Huebl in Dumbo, Brooklyn, on January 31, 2021, as his tonal ivory layers provide a refined counterpoint to her bold winter styling

German model-slash-photographer Johannes Huebl opted for an all-white look, wearing a long coat over a zipped-up waistcoat and a beige rib-knit turtleneck sweater. He also rocked white corduroy pants and light brown shoes.

Keeping a neat and trendy look, the German model accessorized with a gray knit beanie, black gloves, and a patterned fabric face mask.

Johannes Huebl opts for an all-white winter outfit with a gray beanie and a pair of light brown shoes

On the other hand, his fashion-influencer wife, Olivia Palermo, chose a leopard-print coat with a hot-pink fur collar from Cara Mila. It’s the same coat she wore while on a stroll with her husband two weeks earlier.

This time, she wore it over a brown ribbed turtleneck sweater and a pair of light blue, cuffed, ripped jeans.

Olivia Palermo wears a leopard coat with a pink fur trim over a brown sweater and a pair of jeans

Pulling her hair back into a neat, slick bun, Olivia styled her look with a simple pair of stud earrings. She tried to keep a low profile with Le Specs Liar Liar cat-eye tortoiseshell sunglasses.

Olivia Palermo frames her brown leopard-print mink coat with a vibrant hot-pink fur collar, adding a bold pop of color to her neutral turtleneck and understated winter accessories

With her blue jeans rolled up, Olivia revealed her orange socks, which complemented her two-tone shoes.

She wore a pair of leather loafers from the luxury handmade Italian shoe label, Santoni. Similar to their classic shoe designs, Olivia’s loafers feature a double-buckled monk strap. They also have a two-tone look and lugged soles.

A close-up of Olivia Palermo’s chunky Santoni double-monk loafers highlights their rich brown leather, silver buckle straps, and lug soles, with mustard ribbed socks adding a bold pop of color beneath rolled-cuff jeans

Palermo didn’t rely exclusively on boots throughout the season. For a solo neighborhood walk, she paired saturated accessories with layered winter clothing to add contrast.

Roger Vivier “Love Vivi” Pumps Add a Flash of Pink to Palermo’s Winter Denim

Olivia Palermo layers a feather-trimmed black coat over rolled-cuff jeans and finishes the unexpected winter look with hot pink Roger Vivier “Love Vivi” satin pumps and sheer polka-dot socks during a solo stroll in Dumbo, Brooklyn, on January 27, 2021

Rather than relying on neutral footwear, Palermo introduced color with hot-pink Roger Vivier pumps layered over dark cutout socks, creating contrast against otherwise muted winter separates.

She also wore a cream-colored rib-knit sweater underneath her quirky knee-length dress.

Olivia Palermo wearing a dramatic black Pologeorgis “Harlow” mink coat with feather-trim embroidery, cuffed jeans, and hot-pink pumps that instantly brighten the monochrome look

With her hair pulled back into a ponytail, Olivia shielded her eyes with a pair of oversized sunglasses and a black face mask.

Olivia Palermo ties her hair back and stays safe with a black face mask

To ramp up the quirkiness, Olivia wore dark purple cutout socks before slipping into hot pink Roger Vivier Love Vivi pumps.

A close-up of Olivia Palermo’s hot pink Roger Vivier “Love Vivi” satin pumps showcases their sculptural curved heels and pointed toes, styled with sheer black polka-dot socks beneath rolled-cuff jeans

These satin pumps feature cutout vamps, pointed toes, and about 4-inch lacquered heels.

Roger Vivier’s “Love Vivi” satin pumps in vibrant fuchsia feature elegant pointed toes and the collection’s signature sculptural curved heels

Reuniting with Johannes Huebl a few days earlier, Palermo returned to one of her most-worn boot styles.

Dior “Rebelle Army” Boots Add Structure to Her Leopard-Print Cara Mila Coat

Olivia Palermo and her husband Johannes Huebl go out for a stroll in Brooklyn on January 23, 2021 (Credit: Instar / WENN)

Looking warm and chic, the style maven bundled up in a leopard-print coat worn over a ribbed cream-colored turtleneck sweater.

Her bright pink fur collar elevated the look, creating a chic contrast with the rather neutral dark outfit.

Olivia Palermo brightens her winter wardrobe with a Cara Mila leopard-print coat trimmed in vibrant pink fur, carrying a purple Delvaux Brilliant bag, and grounding the look with glossy Dior Rebelle Army combat boots

Olivia wore a pair of blue slim-fit jeans tucked into patent-leather combat boots from Dior. The Rebelle Army boots have a shiny finish, silver metal studs, and chunky soles. She previously styled the same boots with a monochrome blue ribbed-knit sweater and a Max&Co. tulle midi skirt.

A close-up of Olivia Palermo’s glossy Dior Rebelle Army combat boots highlights their polished patent leather, silver-tone studded eyelets, lace-up front, and rugged lug soles

Olivia further accessorized her winter outfit with a Delvaux Brilliant bag, adding a pop of purple to her look. The rich socialite styled her brown locks in a tight, sleek bun, showcasing a couple of her gold stud earrings.

In an attempt to keep a low profile, she wore oversized tortoise-framed sunglasses and stayed safe behind a black face mask.

Olivia Palermo adds a purple Delvaux Brilliant bag and tortoise-framed sunglasses to her look

Her German husband looked handsome in a navy suit paired with a matching coat, a white shirt underneath, and a printed ascot tie.

Wearing a black face mask, Johannes Huebl dressed down the look a bit by adding a gray ski cap and suede loafers.

Olivia Palermo’s German husband, Johannes Huebl, looks equally stylish in a navy suit and suede loafers

Earlier in the month, she embraced a more playful approach, using footwear—not the coat—as the statement piece.

Inuikii Yellow Shearling Sneaker Boots Turn Neutral Winter Layers Into a Statement

Olivia Palermo brightens a winter stroll in Brooklyn on January 19, 2021, pairing a teal Cara Mila leopard-print coat with vibrant yellow Inuikii shearling sneaker boots and striped socks for a bold cold-weather look

She turned heads in a teal-colored leopard-print coat from luxury fur coat and jacket brand Cara Mila. The Bianca Kopenhagen soft mink fur coat features a swing silhouette elevated with a Saga silver fox fur collar.

She wore her striking coat over a neutral-colored outfit that included a ribbed sweater and black leggings.

Olivia Palermo turns heads in a teal Cara Mila leopard mink fur coat and yellow boots

With her light brown hair pulled back, Olivia accessorized the look with a pair of Salvatore Ferragamo colorblock cutout cat-eye sunglasses. She also wore a black face mask.

Olivia Palermo styles her look with Salvatore Ferragamo cat-eye sunglasses

Not one to shy away from a fashion risk, Olivia rounded out her look with a vibrant pair of striped yellow socks to match her equally vibrant yellow boots from Inuikii, a footwear label whose name derives from the Eskimo-Aleut language.

Founded in 2012, the Zurich-based footwear label specializes in fashionable winter shoes and boots.

A close-up of Olivia Palermo’s bright yellow Inuikii shearling sneaker boots showcases their suede uppers, rope laces, and gum soles, paired with striped athletic socks

Olivia opted for their iconic yellow classic sneaker-style ankle boots, which “represent Inuikii’s commitment to combining practical form and function with timeless style.”

The handcrafted Inuikii boots feature a suede upper with soft shearling lining, water-resistant quality, snowproof properties, and anti-slip rubber soles.

This yellow winter sneaker features shearling that will keep you warm and comfortable

The series begins with one of Palermo’s simplest winter looks, illustrating how versatile a well-designed pair of combat boots can be across multiple outfits.

Gianvito Rossi Black Combat Boots Finish Palermo’s Minimal Brooklyn Winter Look

Another January outing showed Palermo relying on an almost monochrome palette, letting texture—not color—create visual interest.

Olivia Palermo keeps her winter style understated during a solo shopping trip in Brooklyn on January 11, 2021, pairing a shaggy black Pologeorgis fur jacket with leather-look leggings and black Gianvito Rossi combat boots for a streamlined cold-weather look

The former reality TV star simply wore her thick, ribbed, high-neck cream sweater with the winter staple pleather leggings. Adding luxe to her all-black look was her shaggy black fur jacket from luxury fur coat and jacket label Pologeorgis.

Olivia Palermo teams a black Pologeorgis shaggy jacket with black pleather pants

She then styled her honey tresses straight with a thick black headband. The American socialite wore a leopard-print face mask and kept a low profile with Salvatore Ferragamo cat-eye sunglasses.

Olivia Palermo keeps it chic with a black headband, cat-eye sunnies, and leopard-print face mask

A pair of her favorite Gianvito Rossi combat boots rounded out her chic street-style look.

A close-up of Olivia Palermo’s black Gianvito Rossi combat boots highlights their smooth leather construction, lace-up design, silver-tone eyelets, and sturdy lug soles, illustrating why the versatile style became a recurring favorite throughout her winter wardrobe

A few months earlier, Olivia styled the same boots with a pink houndstooth coat, a sheer midi skirt, and a gray sweater.

Elevate your street-storming style with this black Italian-made boot of fine leather with a classic lug sole and a ribbed panel wrapping the back

Why Olivia Palermo’s 2021 Winter Shoes Still Feel Relevant Today

More than five years later, Olivia Palermo’s winter footwear remains surprisingly current because she invested in silhouettes that luxury brands continue to reinterpret rather than short-lived seasonal trends. Lug-sole combat boots, polished double-monk loafers, over-the-knee boots, and sculptural pumps have all remained fixtures in designer collections, making these outfits feel as wearable today as they did during New York City’s snowy winter of 2021.

Although Palermo’s exact Dior Rebelle Army and Gianvito Rossi “Martis” boots have become increasingly difficult to source, similar silhouettes remain available through Farfetch’s pre-owned marketplace.

As of June 2026, shoppers could find archival Dior combat styles such as the D-Venture, Diorcamp, Diorally, and D-Circus boots alongside Gianvito Rossi favorites, including the Thurlow, Suzan, Moka, Vamp, and buckled lace-up combat boots, making it easier to capture the same blend of luxury and practicality that defines Palermo’s winter wardrobe.

Gianvito Rossi continues to refine elegant combat and tall boots; Santoni’s handcrafted loafers remain wardrobe staples; Roger Vivier still offers its signature sculptural pumps; and Inuikii continues to produce fashion-forward winter boots built for cold-weather wear.

That lasting relevance is what makes Palermo’s wardrobe stand out. Rather than relying on trend-driven statement pieces, she repeatedly built outfits around thoughtfully designed footwear that balanced practicality with luxury craftsmanship. The result is a collection of winter looks that continues to inspire, proving that great shoes often outlast the fashions surrounding them.