Osborne Florist

About Osborne Florist: From Banking to Blooms

Oriana didn't plan to become a florist.

After twelve years at a bank, she was still trying to figure out what she truly wanted to do. When her father passed away at 33, everything stopped.

At the funeral, surrounded by flowers she'd ordered from Angie Le Cherbo, an Italian florist she'd known for years, Oriana couldn't stop talking about how beautiful they were. Her best friend asked, "Why don't you take a florist course?"

The idea lit something up.

Oriana went to Angie and asked where she could take classes. Angie's response: "Hang out with me. Pay me what you'd pay a course. I'll teach you everything." Oriana left banking and started learning. She loved the craft, the colour and the problem-solving immediately.

Angie rented Oriana space in the shop to start a gift basket business while she learned floristry on the side—work in exchange for mentorship. Years later, after Angie's husband experienced a health crisis, the family decided to sell. Oriana bought the shop and the building.

Thirty years later, she is still following Angie's playbook: own the business, own the property and make it last. The building now houses the flower shop, an Airbnb upstairs and Manitoba Premier Wab Kinew's constituency office.

Inside the Shop

Walk in and you'll see flowers painted on the garage and along the building's side. Inside, there are usually three dogs and a cat wandering around. People come in to see them, and Oriana has never been good at saying no to a sad animal story.

The team runs eight to ten people depending on the season, with every generation represented. "When I see them working together," Oriana says, "one's coming from experience, one's bringing fresh ideas. It's really cool."

Lauren Gaudino manages the shop. She's half-Italian—Oriana jokes that this carries on Angie's legacy.

Eileen brings 15 to 20 years of experience and American florist training. During the Christmas rush, she can work from 7 AM to midnight without complaint. She gets it done.

Allison started as a 15-year-old volunteer through a school program. Now over 30 and becoming a psychologist, she still works here once a week because she loves it.

Jeremy grew up on a flower farm in British Columbia. Today, he is one of Osborne Florist's special hires and runs Tendril, his own small flower farm in Winnipeg. He grows flowers for the shop, and the team has already requested specific varieties for next year's growing season.

Andy—Fred's mom—is a talented floral designer who also makes the custom beaded earrings sold in the shop.

Kennedy is the team's social media specialist, artist and floral designer. Around here, there is very little she can't do.

Norma is the newest hire, a seasoned floral professional with more than 25 years in the business.

How It Works

Each morning begins with quality checks on anything time-sensitive. Most orders are made the night before, then wrapped, boxed and triple-checked. Same-day orders are built while the phones ring. Inventory management never stops, and Lauren keeps the shop spotless—cleaning is her therapy, she says.

Funeral flowers receive special treatment: they go out the day of the service only. Freshness matters when people are grieving.

Weddings bring a different energy. The team isn't large, but when they commit to a wedding, they go all in—hyperfocused and checking every detail.

The Neighborhood Connection

Osborne Florist is a member of the South Osborne Legion, providing flowers and helping with fundraisers and pizza nights. Its Business of the Week program delivers free flowers to shops along the strip and keeps the neighbourhood connected.

Summer brings flowers from Manitoba growers. The shop also has strong working relationships with flower wholesalers here in Winnipeg, helping the team source the right flowers throughout the year. Year-round, the shop carries local honey, cookies, chocolate and tea. A signature offering is a teacup arrangement paired with local tea: flowers to enjoy, then a cup to keep.

Northern Manitoba's Indigenous communities often lack local florists. When someone up north needs funeral flowers, Osborne builds the piece at the last minute and ships it north—a service rooted in understanding Manitoba's geography.

Why Choose Local?

Flexibility. That's Oriana's answer.

"We're open seven days. Need an order at 7 AM? Done. Midnight? We'll make it happen." Oriana has delivered on Christmas Day and made same-day wedding bouquets when other florists backed out.

Oriana also believes flower shops need young people and fresh ideas. "You don't have people challenging you? You get stuck in 2005. You have to stay relevant or you'll die like a dinosaur."

Look for the building with flowers painted everywhere. The Premier's office is inside. Dogs and a cat are almost guaranteed. If it matters to you, it matters here.