Jeffrey and Ryan, both from Wolcott, Connecticut, brought a big dose of style and personality to Villa Michaela in Tuscany. Jeffrey, a choreographer, and Ryan, an interior designer, leaned into their love of fashion (and a serious 90s obsession), to create a wedding that was bold, playful and unapologetically them. From the ceremony to the after-party, every detail was packed with personality, and with a huge focus on guest experience, everyone left feeling part of something truly special with memories that will last a lifetime.

The Rehearsal

Love Story

“We started dating several years ago, after meeting through the dance world. We later bought our first home in town and completely renovated and transformed it. Jeffrey ended up proposing to me in that very house that we built together. He got down on one knee in our kitchen with our dog by his side; it was the perfect proposal. It was so special to have it in our home, where we’ve built our lives together and plan to grow our family. It was one of the most special memories, and we get reminded of this moment every time we step into our kitchen.”

Why Italy

“We have such a connection to Italy as we had traveled there together and fell in love with the history and charm that only Italy has to offer. We knew how much our friends and family would love Tuscany and most of our guests hadn’t experienced it yet, so it was the perfect way to give our guests a once in a lifetime memory in such a beautiful place.”

The Venue

“Once we found the Villa, we knew it was where we had to get married; it had the perfect amount of authentic charm. As we walked through the property and stumbled upon the vine-covered archway, we immediately pictured the perfect alfresco dining area for our wedding. We could envision beautiful chandeliers strung from the vines and a long table to host our friends and family. When we walked into the sixteenth-century chapel on the Villa’s property, we were sold. Marble checkered floors, stained-glass windows, and charm that could not be replicated. We knew in that moment we had to get married in that chapel. We truly fell in love with the character and charm of the property, and every choice we made during the wedding planning process was to enhance the Villa’s uniqueness.”

Stand Out Moment

“One of our favourite moments from our wedding was the bells ringing from the church in the village. It’s a tradition that, when someone is getting married, they ring the church bells in celebration. The bells rang as we walked down the aisle and even as we exited the chapel. It was the most perfect detail on our wedding day, and it wasn’t even something we planned. I think it’s such a metaphor for wedding planning: you can plan and plan and plan, but the best parts of your day will be the things that just happen, the things you can’t plan.”

The Budget

“We didn’t go into the planning process with a set budget in mind, as we felt there were certain elements or ideas we were unwavering on including. It was also a learning experience, as we were not as versed in the cost differences between the US and Italy. As we started to check things off our list, we were able to track where we were spending and then continue from there. When all was said and done, we found there are ways to achieve exactly what you want without having to overspend on everything. We found a careful balance between splurges and saving and wouldn’t have changed a single thing.”

The Inspiration

“When sourcing wedding inspiration I was very drawn to 90s romantic comedy movies, similar to the wedding from Father of the Bride. When I stumbled upon a 90s Vera Wang veil while shopping with my mom at a vintage bridal shop, I had to have it. It ended up being the jumping off point for everything else I chose. Everything had to work with the veil!

My personal style is a bit daring — I love a mix of old and new and I’m not afraid of an out-of-the-box accessory. I have always been fashion obsessed and always picking up vintage pieces to add to my closet; I don’t think an outfit is complete without a vintage touch.

This thread of classic and timeless elements helped us make every choice for our wedding. From vendors to outfits, we wanted everything to feel classic and authentic to us.”

Tennis court at italian wedding venue, Villa Michaela

The Outfits

“I couldn’t imagine being married in something that wasn’t vintage; I wouldn’t feel like myself. I paired my Vera Wang veil with a custom handmade Italian silk hat to make it my own. I knew I wanted to contrast the soft elements of the veil with something more structured.

I came across the perfect tuxedo from Khaite, a New York City-based company, with exaggerated shoulder pads and pleated flair pants. After a few alterations, like custom fabric-covered buttons, it was the perfect combination to contrast the veil with the tuxedo’s clean lines. I even sourced a vintage Oscar de la Renta tuxedo shirt with ruffle detail, famously worn in the gay prom episode of Sex and the City.

Jeffrey went for a classic look as well. Inspired by the Italian setting, a custom tailored Gucci tuxedo was the answer. He even found vintage Gucci cufflinks to tie his look together.”

Best Money Spent

“I would consider our best money spent on everything related to the guests’ experience. We both love to host, so for us we were extremely focused on our guests’ experience. We went out of our way to make sure they had an over-the-top, once-in-a-lifetime experience. Whether it was selecting the perfect food or music, organising all the transportation, tours and events, we really wanted every detail to feel curated and thoughtful for our guests. We even got a gelato cart. We wanted everyone to be able to let loose and have a good time, and I think we accomplished just that.”

Advice For Couples

“I would say that no matter how much work you put into every single detail, your favourite parts will end up being the ones you didn’t plan.

You can agonise over what color napkins to choose or what flowers you want, but your stand out memories will be the things that happened organically.”

VENDOR TEAM

Ryan + Jeffrey’s softly nostalgic Tuscan wedding

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Ryan + Jeffrey’s softly nostalgic Tuscan wedding

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