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Dee Ocleppo-Hilfiger Chats Fashion, Grocery Store Glam and More on New Livestream Show

As an extension of her namesake shoe and accessories line, Dee Ocleppo-Hilfiger has officially launched her first livestream show, “Dee Tales with Dee Ocleppo.” The designer’s debut episode launched on Sunday, featuring Glam 4 Good founder and stylist Mary Alice Stephenson.

Ocleppo and Stephenson took to the web from Ocleppo-Hilfiger’s living room to share an inside look at her brand’s new styles, as well as their advice on fashion, travel and everything in between. The duo made sure to do so in a cozy manner, however, each wearing a monogrammed cashmere sweater from Ocleppo-Hilfiger’s own line — plus a glass of wine, an accessory that never goes out of style.

Ocleppo-Hilfiger took time to share some of her creative inspirations — including the idea behind her new cashmere sweater, beanie and scarf line, which she says can be worn dressed up or down. “I was watching an episode of ‘Laverne and Shirley,’ and she had on this incredible sweater with a giant ‘L’ on it. And I was watching, and I was thinking, ‘Oh my god, I love her sweater! I wish I had one with a ‘D,’” said Ocleppo-Hilfiger. “I love that idea — we need to bring that back. And I literally got inspired by watching TV during the pandemic, so it just goes to show you that you can get inspiration from anywhere, anytime, if you’re open to it.”

Dee Ocleppo-Hilfiger, Mary Alice Stephenson, Dee Ocleppo, pumps, combat boots, breast cancer awareness month, Dee Tales
Dee Ocleppo-Hilfiger and Mary Alice Stephenson on “Dee Tales.”
CREDIT: Courtesy of DeeOcleppo.com

Dee Ocleppo’s fall footwear collection incorporates a range of styles that combine the designer’s classic and glamorous aesthetics, including a chic take on the lug-sole boot trend. “I feel like a lot of women, they’re afraid to wear a combat boot, and they think it’s too much of an edge,” said Stephenson. “But the truth is that it actually elongate your leg, and it is sexy. Styling Jennifer Lopez, styling Beyoncé, they all loved a combat boot, and they would do it because it would actually make them look longer and leaner.”

Ocleppo-Hilfiger agreed, adding how the boots are ideal to transition seasons due to their approachable height and chunky soles.

The duo also discussed their likes and dislikes in a humorous segment called “Amore/No Amore,” where Ocleppo-Hilfiger shared her dislike for dressing up in “high glam” while grocery shopping. “If I went high glam to the grocery store, my husband would think I’m having an affair,” she joked. “Where am I going? I’m going to the grocery store! I’m married, I don’t need to glam to the grocery store. That’s for the single ladies, not for me.”

However, the designer stated that her pointed-toe satin Cinderella pumps, while glamorous, can be worn by anyone for any activity. “I have to admit, I didn’t really design them to go to the grocery store, but hey! Knock yourself out,” she said. “If you would like to wear these to the grocery store, you can.”

Dee Ocleppo-Hilfiger, Mary Alice Stephenson, Dee Ocleppo, Cinderella pumps, pointed-toe pumps, pumps, combat boots, breast cancer awareness month, Dee Tales
Dee Ocleppo’s Cindarella pumps.
CREDIT: Courtesy of Dee Ocleppo

As fall arrives, several users in the comments additionally asked about footwear styling rules during colder weather — and, naturally, Stephenson and Ocleppo-Hilfiger had the answer. “I think these boots with a dress or skirt, it’s a cool look,” Ocleppo-Hilfiger shared, referencing her own lace-up Autumn combat boots.

“I love the Snowy Day boots,” Stephenson said, referring to Ocleppo-Hilfiger’s new lug-sole Chelsea boots. “I wear these with a dress all the time. Even my maxi dresses from spring, summer. I’ll just throw on a boot and a great hoodie over it, and that looks very chic.”

Ocleppo-Hilfiger closed her show’s first episode by sharing the deeper meaning behind her footwear’s signature bubblegum pink soles. “We actually donate 10% of all the proceeds of all the pink-soled shoes to BCRF [Breast Cancer Research Foundation],” she said. “October is Breast Cancer [Awareness] month, and it’s super, super important for awareness for you guys out there. Please make sure to have your yearly exam. And that’s my public service announcement for today!”

You can tune in to “Dee Tales” live episodes on DeeOcleppo.com.

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