Olivia Culpo Pulls Off ’90s Throwback Fashion in Princess Polly Bustier Top and High-Rise Flared Jeans

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She’s known for her incredibly fit figure and great sense of style. In February 2022, Olivia Culpo showed off both while attending the Michael Kors Fall 2022 runway presentation during New York Fashion Week.

Olivia Culpo parading her legs at the Michael Kors Fall 2022 runway presentation during New York Fashion Week on February 15, 2022Olivia Culpo parading her legs at the Michael Kors Fall 2022 runway presentation during New York Fashion Week on February 15, 2022 (Credit: Roger Wong / INSTARimages)

A Dazzling Silver Slip Dress Paired With a Chic Oversized Blazer

The fashion influencer couldn’t be missed in her sparkling silver outfit from American fashion designer Michael Kors. Showing off her legs and a hint of cleavage, Olivia wore a silver slip dress hand-embroidered with crystals.

She layered the look underneath an oversized white blazer from the American fashion label’s Fall 2021 collection.

Olivia Culpo sparkles in a Michael Kors crystal-embellished slip dress and an oversized white blazerOlivia Culpo sparkles in a Michael Kors crystal-embellished slip dress and an oversized white blazer (Credit: Roger Wong / INSTARimages)

Matching Accessories: Silver Earrings and Aquazzura Sandals

Keeping her neck bare, Olivia accessorized with silver chandelier earrings, which perfectly matched her Aquazzura So Nude sandals in mirrored silver leather.

Olivia’s choice of footwear was just as dazzling as her outfit. She elevated her look with the Aquazzura So Nude sandals, a sleek and timeless design featuring mirrored silver patent leather, a delicate slingback strap, and a chic 4-inch stiletto heel. A favorite among fashion-forward celebrities, these sandals are available in a wide range of colors at Mytheresa.

Olivia Culpo teams her white ensemble with mirror patent silver heels from AquazzuraOlivia Culpo teams her white ensemble with mirror patent silver heels from Aquazzura (Credit: Roger Wong / INSTARimages)

Olivia Culpo isn’t the only celebrity captivated by Aquazzura’s ‘So Nude’ sandals. Sarah Jessica Parker was spotted wearing a raffia version of these heels on the set of “And Just Like That…”.

Similarly, Katy Perry embraced the minimalist elegance of the ‘So Nude’ sandals, pairing them with a barely-there dress that showcased her impeccable style. These instances highlight the ‘So Nude’ sandals’ versatility and appeal among fashion-forward celebrities.

These light-catching Aquazzura So Nude sandals have silver patent slingback straps and toe strapsThese light-catching Aquazzura So Nude sandals have silver patent slingback straps and toe straps

Olivia Culpo Rocks a ‘90s-Inspired Street Style Look in LA

Proving her street-style game is as strong as her red-carpet fashion game, Olivia hit the LA streets in a 90s-inspired outfit that displayed her cleavage.

Olivia Culpo nails street style game while out and about in Los Angeles on February 12, 2022Olivia Culpo nails street style game while out and about in Los Angeles on February 12, 2022 (Credit: Michael Simon / startraksphoto)

The former Miss Universe wore a $47 Princess Polly “Kaeshia” white rib bustier top with a pair of Isabel Marant “Jean Lemony” jeans.

These high-rise flared jeans are light blue cotton denim and feature wide-cut legs that flare out gradually from below the hips.

Olivia Culpo pairs a Princess Polly white bustier crop top with '90s-style high-rise flared jeans from Isabel MarantOlivia Culpo pairs a Princess Polly white bustier crop top with ’90s-style high-rise flared jeans from Isabel Marant (Credit: Michael Simon / Startraksphoto)

Adding a Pop of Color With a Peony Pink Handbag

Adding color to the look, Olivia carried a $1,250 Patou “Le Patou” bag in peony pink leather over her shoulder. It boasts a half-circle shape with geometric cutouts and an adjustable strap that can be carried across the body, on the shoulder, or by hand.

In 2024, Anne Hathaway elegantly showcased a white Patou Le Patou bag with a matching ensemble featuring a Patou cropped quilted jacket, a terry-cloth quilted mini dress, Calzedonia 50 denier total comfort soft touch tights, Manolo Blahnik BB pumps and exquisite Bvlgari jewelry including the Serpenti Viper and Divas Dream rings.

Olivia Culpo adds color to her outfit with Patou Le Patou peony pink bagOlivia Culpo adds color to her outfit with a Patou Le Patou peony pink bag (Credit: Michael Simon / Startraksphoto)

Elevating the Look With Air Jordan 1 Retro Sneakers

Wearing her shiny tresses in waves, Nick Jonas’ ex finished her street-chic outfit with Air Jordan 1 Retro High OG sneakers in a green and white colorway.

An all-time favorite, the Air Jordan 1 Retro High features a classic high-top silhouette with the signature Swoosh logo detail, Air Jordan logo, and perforated vamps.

Olivia Culpo finishes off her street style outfit with Air Jordan 1 Retro High OG sneakersOlivia Culpo finishes off her street-style outfit with Air Jordan 1 Retro High OG sneakers (Credit: Michael Simon / Startraksphoto)

Olivia Culpo’s choice of the Air Jordan 1 Retro High OG sneakers underscores the enduring appeal of this iconic silhouette. Initially released in 1985 as Nike’s first signature sneaker for Michael Jordan, the Air Jordan 1 has transcended its basketball origins to become a staple in both streetwear and high fashion.

Celebrities like Hailey Bieber have been spotted rocking the Air Jordan 1 Retro High, highlighting its versatility and timeless design.

To explore more about this classic sneaker, our guide on the most popular Nike shoes delves into the history and cultural impact of the Air Jordan 1.

Done in green and white colorway, the Air Jordan Retro 1 High OG features a classic high-top silhouette and signature logo detailingDone in a green and white colorway, the Air Jordan Retro 1 High OG features a classic high-top silhouette and signature logo detailing

Olivia Culpo Turns Heads in a Bold Night-Out Look

As for her evening outfits, Olivia never disappoints. She was spotted enjoying a night out with her friends at Craig’s in West Hollywood, and she definitely got heads turning.

Olivia Culpo enjoys a night out with friends at Craig's in West Hollywood on January 25, 2022Olivia Culpo enjoys a night out with friends at Craig’s in West Hollywood on January 25, 2022 (Credit: BauerGriffin / INSTARimages)

A Sheer Statement Blouse Styled With Classic Denim

Never one to shy away from flashing some flesh, the former beauty queen put her toned abs on display in a sheer cropped black blouse from Tbilisi-based Georgian fashion designer Anouki.

The see-through top, which gave a glimpse of her silk lace bra, features a dramatic voluminous silhouette, a twisted front, short puff sleeves, a V-neck, and a daring asymmetric hem.

Olivia Culpo flashes her abs in Anouki see-through blouse and straight-leg jeansOlivia Culpo flashes her abs in Anouki see-through blouse and straight-leg jeans (Credit: BauerGriffin / INSTARimages)

Finishing Touches: Sleek Hair, Rosy Makeup, and Edgy Boots

Christian McCaffrey’s girlfriend kept the bottom half of her outfit simple, allowing her statement-making blouse to stand out. She wore high-waist straight-leg jeans in charcoal gray, styled with a silver chain belt.

Open about her endometriosis diagnosis, Olivia glammed up with winged eyeliner, mascara, bold brows, and rosy lip color. She styled her sleek hair in a low bun that helped showcase her silver hoop earrings.

Olivia Culpo glams up with winged eyeliner, rosy lipstick, and sleek low bun hairstyleOlivia Culpo glams up with winged eyeliner, rosy lipstick, and a sleek low bun hairstyle (Credit: BauerGriffin / INSTARimages)

To finish her night-out outfit, Olivia carried a small black leather bag with braided handles and elevated her height by a few inches with black leather boots.

Olivia Culpo’s Best Boot Moments: Elevating Every Look with Statement Footwear

Olivia Culpo’s affinity for boots is evident in her diverse fashion choices. At the 2023 Revolve Festival, she embraced a cowgirl-inspired look, pairing Paris Texas 100mm El Dorado embellished toe boots with Levi’s Ribcage denim cutoffs and a black cowboy hat.

In another instance, Olivia showcased her legs in black Gianvito Rossi Eiko leather-heeled boots while dining with her sister Sophia at Craig’s in West Hollywood.

Demonstrating her versatility, she also donned Saint Laurent ‘Niki’ glossed-leather knee boots, styling them with a Gucci ‘Coco Capitan’ logo shirt and GRLFRND skinny jeans for a chic streetwear ensemble.

These varied boot choices highlight Olivia’s ability to incorporate statement footwear into her outfits seamlessly, inspiring fashion enthusiasts to explore similar styles.

Olivia Culpo completes a night out look with pointy black leather Chelsea bootsOlivia Culpo completes a night out look with pointy black leather Chelsea boots (Credit: BauerGriffin / INSTARimages)

Stepping Out in Style: Celebrities Who Love Black Leather Chelsea Boots

Black leather Chelsea boots have long been a staple in celebrity wardrobes, effortlessly blending style and versatility. From casual streetwear to polished ensembles, these sleek boots are a go-to choice for many fashion-forward stars.

Ana de Armas Elevates Casual Chic

Olivia Palermo Celebrates in Gianvito Rossi Chelsea Boots

Lucy Hale Keeps It Edgy in Bottega Veneta BV Lug Chelsea Boots

These moments highlight the enduring popularity of black leather Chelsea boots among celebrities, solidifying their status as a must-have footwear choice for any season.

Olivia Culpo: A Masterclass in Footwear Versatility

Whether she’s strutting down the streets of LA in retro sneakers, turning heads in sky-high stilettos, or embracing the effortless cool of knee-high and Chelsea boots, Olivia Culpo consistently proves that the right footwear is the foundation of a standout outfit.

Her ability to seamlessly transition from ’90s-inspired denim to Western-chic boots and ultra-glam heels cements her status as a true style chameleon. Whether you’re looking for inspiration for a polished evening look, casual streetwear, or red carpet glam, Olivia’s fashion choices serve as the ultimate guide.

For more celebrity shoe inspiration, check out our deep dives into the most iconic Nike sneakers or explore how A-listers are styling the metallic shoe trend. After all, as Olivia Culpo proves, the perfect pair of shoes can make any outfit unforgettable.