Olivia Culpo Masters Winter Styling in Bold Chunky Sweater and Brown Leather Boots

If you purchase an independently reviewed product or service through a link on our website, Footwear News may receive an affiliate commission.

Olivia Culpo reminisces on her success in her latest then vs. now post.

The socialite and entrepreneur posted a photoset on Instagram yesterday that featured her and her dad celebrating the achievements she’s made with her Rhode Island-based restaurants Back 40 and the newest endeavor, Union & Main.

“My dad and I when @back40ri was under construction 4 years ago vs now at @union_and_main under construction. Ever since I was little I watched my dad work his butt off in the restaurant industry to support me and my 4 siblings,” Culpo said. “He worked his way up from the bottom and little by little found success while continuing to create opportunity for the people around him. I always admired his hard work and it was a goal for me to be able to work in the restaurant world in some capacity when I grew up. It’s even sweeter that now I get to do it with my family. I’m so grateful to be able to do these projects w my fam and share great food and experience with everyone who comes into the restaurant ❤️❤️To everyone behind @back40ri + @union_and_main, thank you so much for all that you do! I can’t take ANY credit for making these places run on a daily basis so you deserve all the praise and you know who you are 🌟❤️ And if any of you ever find yourself in Rhode Island, come on in !”

For the ensembles in the pictures, Culpo donned a white fringed dress that had dramatic shoulders, a turtleneck and a short hemline. She accessorized the statement-making piece with a brown poofy clutch. And for the other ensemble, Culpo wore a monochromatic black look incorporating a jacket with shoulder detailing, black skinny jeans and a black quilted Saint Laurent bag.

When it came down to the shoes for both of these knock-out looks, she wore a pair of tall brown leather stiletto boots and a pair of black loafers that incorporated a plethora of buckles.

Culpo is known for her signature and statement-making fashion choices that allow her to have fun. Throughout her Instagram feed are pictures of her wearing intricate bikinis, delicate leather pieces, slouchy sweaters and durable denim that help her execute her chic vision. When it comes to her footwear, on the other hand, she has an affinity for pumps, sandals and boots that all add that special Culpo flair to her getups. Also some of her favorite brands to don her feet are Jacquemus, Vince Camuto, Bottega Veneta and Gia Borghini.

Flip through the gallery to see Olivia Culpo’s best street style moments. 

Aldo Oluria Knee-High Boot

To Buy: Aldo Oluria Knee-High Boot, $120

Franco Forla Tall Boot
CREDIT: Franco Sarto

To Buy: Franco Forla Tall Boot, $150. 

Sam Edelman Taelor Loafers
CREDIT: Sam Edelman

To Buy: Sam Edelman Taelor Loafers, $150

Access exclusive content