Street Style: Meet Kara Tomaiolo
I honestly can’t remember the exact moment I met Kara, it must have been more than a decade ago, and I’m pretty sure Hollyn was involved. And that makes perfect sense, because if you know Kara, you know Hollyn. Their friendship is one of those rare, enviable bonds that goes far beyond “friendship.” They’re more like family: loyal, supportive, and endlessly fun together.
Like so many Alexandria connections, my relationship with Kara grew through mutual friends, neighborhood activities, and of course…exercise. People talk about wanting “Jennifer Aniston arms.” Well, Kara is the Alexandria version—she has the best arms in town. We worked out together for a while (spoiler: I didn’t achieve her arms), but those mornings in the garage gave me something better: time to really get to know her.
Kara Tomaiolo
Styled by: Ali Hellmuth, ALH Style & Elizabeth Todd, The Shoe Hive/The Hive
Hair and Makeup: Myself – with help of Deidre’s skincare at Alternative Health Associates
Photography: Renée C. Gage Photography
Shoot location: Kara’s home in Seminary Hill, Alexandria
What stands out most about Kara isn’t her fitness or even her style, it’s her character. She’s that rare mix of fiercely loyal and refreshingly honest. No nonsense, no fluff, no pretending. And yet, she delivers honesty with humor, kindness, and warmth. It’s a quality that makes you instantly trust her.
And trust is exactly what you want in someone planning your vacations. After years in the corporate world, Kara recently launched her own travel agency, Tomaiolo Travel. She’s always been game for an adventure—whether it’s a spontaneous cocktail or a getaway—so this second act fits her perfectly. She’s the person you want in your corner when it comes to choosing the right itinerary, booking the best experiences, and avoiding the pitfalls of DIY planning. Personally, when my husband finally takes his dad on that train trip across Canada, Kara will be my first call. Because let’s face it, without an expert, that kind of trip could easily go off the rails.
So, Alexandria Stylebook readers, consider this your official introduction: meet your new go-to travel advisor. Trust me, if Kara invites you over for a cocktail, say yes. And if she offers to plan your next trip? Say yes even faster.
Check out Kara’s Street Style:
ABOUT KARA
Neighborhood: Seminary Hill Area
What is your hometown? Shrewsbury, MA
What would surprise people about you? I am an introvert.
Favorite book or movie: Almost Famous
Guilty Pleasure: Online shopping
Latest binge-watch: Black Doves
Bucket list travel destination: So many! Maybe Morocco next.
STYLE
Define your style in three words or less: Elevated, classic, quality pieces.
The go-to piece in your wardrobe: Favorite AG jeans.
Favorite trend: Oversized blazer
Beauty product you can’t live without: One Love Vit E Eye Balm.
Boots, dress shoes or sneakers? Boots, always
WELLNESS
Go-to way to de-stress: Being in Nantucket
Most fun way to stay active: Workout with my group and our trainer & friend, Brandon Maupin
Wellness goal: Creating a home of healthy ingredients – organic, non-GMO, pesticide-free.
Want to try: Cupping massage
Proudest wellness achievement: Leaving my corporate job that I never enjoyed and starting something that I love. Removing that level of stress from my life has had a monumental wellness effect.
HOME
Favorite room in your home: Bedroom/bathroom
Antiques, modern, or a mix? Transitional to modern
Last item bought for your home: Hand-blown glass octopus
Favorite way to entertain: Cocktails, light meal and a good football game by the outside fire.
Clutter-free or well-lived in? Strive for clutter free…
Next planned purchase: It’s not exciting, but a new couch.
ALEXANDRIA
What do you love about Alexandria Stylebook? I love the community that it builds around women. Elizabeth Todd and Ali Hellmuth are great style resources and community energizers!
Favorite spot in Alexandria: Four Five for coffee, The Hive for wardrobe building and Alternative Health Associates for the best facials and skin care in Alexandria!
Your go-to shop: The Hive
Best food spot: Old Town Farmers Market
Annual Alexandria event you most look forward to: The Shop Local events that happen around the holidays. It gives you an opportunity to get out in Old Town and visit stores you don’t frequent regularly.
