Street Style: Meet Todd O’Leary of Visit Alexandria
Todd greets me inside the lounge at the Hotel AKA as we’re both shrugging off the bitter cold – the winter sun is deceiving. He shares that he's originally from East Troy, Wisconsin outside of Milwaukee and because he lived there for almost 40 years, his body should maintain some muscle memory. “But living in California for 11 years definitely made me soft, and we spent three seasons in Northern California, where winter is 50-60 degrees.”
He started off as an intern at the Greater Milwaukee Convention and Visitors Bureau in 1998 where he was bit by the destination travel bug. “I worked my way up from nonpaid intern to director of marketing. I left Milwaukee when I was hired by The San Francisco Travel Association, and was their VP of global partnerships and strategic alliances for five and a half years.” One of Todd’s big moments was helping host Super Bowl 50. “I had never worked in a city that hosted it, and it was San Francisco’s first. There were so many amazing events, and the 50th anniversary of the Summer of Love was also just incredible.”
His next career move led to wine country. “Sonoma is another iconic part of the Bay area, and I was the vice president of marketing and communications at Sonoma County Tourism for almost six years. My husband Mark and I love wine and we got married there in 2017. It was a wonderful experience, because I was able to mesh my personal and professional passions for food and wine.”
So how did he leave the vineyards behind and arrive in Alexandria? “It was a career move. I was the number two in Sonoma County and was ready for a presidency role. My star had been shining more brightly in our industry when I heard of this opportunity (President and CEO of Visit Alexandria).” The incumbent president Patricia Washington had announced her retirement in December. Todd threw his hat in the ring for the role in January of 2024, flew out here in March to interview in person, and accepted the role in April. He left California on Memorial Day weekend and began the trek east. “My dad flew to California from Wisconsin, and it was an epic 3,000-mile, father-son road trip. My dad is in his late 70s and neither of us had ever been to the Grand Canyon. We made it a must-stop and experienced that together.”
Todd O’Leary
President and CEO at Visit Alexandria
Photography: Renée C. Gage Photography
Shoot location: Hotel AKA Alexandria
In June, he flew back for Mark and their two cats. Todd then quickly immersed himself into Alexandria, meeting as many people as possible, “to really get my finger on the pulse of the community and learn its values.”
I first met Todd in June at an opening event held at Atlas Brew Works in Carlyle, so I can personally verify he was experiencing the good stuff, especially Andy’s Pizza. Todd oversees a team of 15 full-time employees at Visit Alexandria, and you will always find at least two of them attending an opening or community event – and many times Todd is part of that duo.
Of Alexandria, he says, “I was immediately impressed. It’s 276 years old and it's not a city stuck in the past. It honors its past and knows its roots, while firmly looking forward. There’s so much flair in this historical place, and it’s been so interesting to learn and experience each of its neighborhoods. Old Town, The West End, Del Ray…and the arts and cultural district that’s growing in North Old Town. Potomac Yard and Virginia Tech’s new innovation campus…the new hotels and the older, established ones…the local shops and business owners.”
He stresses how important the tourism economy is to all of us that live in Alexandria. “Without it, we would all pay a lot more in taxes. Incremental revenue generation means a lot. And as residents, we get to enjoy so many of the same amenities our visitors do.” He adds that Visit Alexandria also aims to attract visitors that treat our community with respect. “It’s not a focus on sheer numbers and quantity – we want quality.”
As someone who has worked in the tourism and hospitality sector his entire career, I’m curious as to his own travel plans. He shares, “Now that we’re on the East Coast, I definitely want to visit Europe more. My husband turned 50 last year, and we flew down to South Africa…a 16-hour flight, but it was absolutely incredible.” He admits that when he travels, his occupation makes him view everything through an additional lens. “I always look at what makes a place unique. Why do people want to visit? What do they want to see? What are some of the customs? What’s the weather like? We were in South Africa in the winter – after leaving a hot, humid D.C. summer!”
What’s on the horizon? “World Pride in D.C. at the end of May into early June…two to three million people are expected to visit the region at that time. We will shine a light on those activities and have some of our own. Further ahead, America will celebrate 250 years in 2026, and we are actively planning for our celebration in Alexandria, and of course, there will be celebrations across Virginia and nationwide.”
Keep your eyes peeled for Todd at the next Alexandria restaurant opening or community event, it’s likely he’ll be there. And until then, check out Todd’s Street Style:
ABOUT TODD
Neighborhood: West End
Hometown: East Troy, WI
What would surprise people about you? That I grew up on a beef cattle farm in Wisconsin.
Favorite movie: Field of Dreams
Guilty Pleasure: A big slice of NY Style cheesecake.
Latest binge-watch: The Bear, Season 3
Bucket list travel destinations: The Seychelles
STYLE
Define your style in three words or less. Classically laid-back
The go-to piece in your wardrobe: My Adam Derrick shoes that I got married in. Even though they’re over eight years old, they’re still in good shape and looking as stylish as ever.
Favorite trend: Oversized sweatshirts
Beauty product you can’t live without: Gotta have my Neutrogena face lotion with SPF.
Boots, dress shoes or sneakers? There’s a time and place for all of them in equal measure!
WELLNESS
Go-to way to de-stress: Enjoying an incredible glass of wine listening to chill music.
Most fun way to stay active: Walking with my husband in Alexandria’s beautiful parks.
Wellness goal: I want to get back into practicing yoga on a regular basis.
Want to try: Acupuncture
Proudest wellness achievement: Losing a significant amount of weight.
HOME
Favorite room in your home: Living Room
Antiques, modern, or a mix? Modern
Last item bought for your home: NordicTrack Elliptical Machine
Favorite way to entertain: Open up good wine, make delicious food, set the vibe with music, and enjoy time with our friends and family.
Clutter-free or well-lived in? Clutter-free
Next planned purchase: Modern leather recliner
ALEXANDRIA
What do you love about Alexandria Stylebook? I love seeing how fellow Alexandrians express their personal styles!
Favorite spot in Alexandria: Having a drink and noshes at Barca Pier.
Your go-to shops: Red Barn Mercantile – it’s always fun to see what Amy and her team have on offer!
Best food spot: Dairy Godmother – we love the taste of home (Wisconsin) with their frozen custard! thedairygodmom
Favorite local organization: Visit Alexandria, of course!
Alexandria event you most look forward to: As a good Irishman, I have to say the St. Patrick’s Day Parade in Old Town, organized by The Ballyshaners.
