Sydney to Las Vegas: Inside Kate and Will’s double wedding

“I really recommend doing whatever you want for your wedding.”

Here at Fashion Journal, we make no secret of our love of weddings. We’re suckers for a bit of romance and have a soft spot for weddings that do things differently, whether it’s a Las Vegas elopement, a tropical getaway or a Town Hall celebration.

Kate O’Loughlin first met her now-husband, Will Bailey, 10 years ago at a New Year’s party in Sydney. “Despite the copious UDLs that night, it really was love at first sight,” she remembers. After eight years together, Will proposed during a holiday in Mexico. Though Kate suspected he already had a ring, the proposal still took her by surprise. The couple’s engagement also happened to fall on Christmas Eve, meaning it was Christmas Day for their family and friends back in Sydney when they found out.

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Two years later, Kate and Will celebrated their nuptials with not one but two weddings. “We started ‘conventional’ wedding planning but it didn’t feel true to us as a couple,” Kate says. Ultimately, they chose to legally tie the knot at a registry in Sydney, followed by an intimate dinner party with their closest friends and family. A week later, they jetted off to Las Vegas to marry again with an Elvis celebrant.

“Will and I felt so drawn to the fun, eclectic and crazy vibes of Las Vegas,” she tells me. “The idea of being in this chaotic and crazy city, laughing together just the two of us was an opportunity we couldn’t pass up… it was both hilarious and incredibly romantic all at once.”

The added benefits of two weddings? Two sets of photographs, multiple chances to declare your love and of course, two wedding dresses. For the Sydney celebration, Kate worked with bridal label Lola Varma to create her silk strapless top and long bubble skirt, fit with a sheer overlay. For Las Vegas, she opted for a two-piece silk corset and skirt from Van Der Kooij.

“I really recommend doing whatever you want for your wedding,” Kate says. “We had the best nights celebrating in a way that felt really true to who we are as a couple.”

Fashion Journal: Hi Kate! Congratulations on both of your beautiful weddings. How did you meet Will and when did you get engaged?

Kate: Will and I met on New Years Eve in 2015 and have been together ever since. I was a fresh-off-the-gap-year 18 year old and he was a cool first-year uni student. Despite the copious UDLs that night, it really was love at first sight.

We got engaged in Mexico in 2023, surrounded by the beautiful clear blue water of Lake Bacalar. I knew he had a ring but had thought he was going to propose in a different location on the same trip, so it was still a surprise which was lovely. It was Christmas Eve over there, making it Christmas Day in Australia, so it was so nice being able to call all our friends and family with the news.

How and where did you celebrate your wedding? 

We celebrated our wedding twice. We legally got married in Sydney at the registry and had a small dinner party celebration that night with immediate family and 20 of our best friends.

The following week, we flew to Las Vegas and had what we consider our ‘proper wedding’ with our Elvis celebrant at the Little White Chapel. Vegas was the most special day as it was just the two of us, and we couldn’t stop laughing at the fact that we were doing it all over again. I kept smiling as our Elvis sang us a rendition of ‘Viva Las Vegas’ after speaking our vowels… it was both hilarious and incredibly romantic all at once.

How did you celebrate in Sydney?

We kicked off the night with ‘bridal party’ drinks at The Hollywood Hotel in Surry Hills, where we exchanged rings under disco balls and vintage beer posters.

Then, we all made our way to Theeca in Darlinghurst, where the rest of our friends met us. We had a beautiful  dinner with custom cocktails that paid homage to our family homes and our dog, Django – the Yamba, the Palm Beach and the ‘Djangtini’.

We had a three-course dinner outside under the stars, and the food and vibes were so immaculate. As a massive foodie and someone who spent my university years working in hospo, it was so important to me to have a genuinely good food and a natural-forward wine list, making Theeca a perfect location.

Throughout the dinner we had a DJ who was mixing vinyl records, which we had asked our guests to bring in place of gifts. Will’s mission in life is to create the ultimate vinyl collection, and it’s so special to us now being able to listen to the albums our friends gave us because they remind us so clearly of the night. We never thought that the Shrek 2 soundtrack would be the backdrop to my wedding, but it honestly goes hard.

What made you decide to get married for a second time in Las Vegas?

We started ‘conventional’ wedding planning but it didn’t feel true to us as a couple. I’ve never dreamed of a big wedding and we’re pretty private with our love, so we didn’t really align with the idea of having a traditional ceremony with public vows.

Will and I also felt so drawn to the fun, eclectic and crazy vibes of Las Vegas. We thought if you’re going to elope, do it right. We’ve always been obsessed with vintage clothes and music, so for me there was nowhere more perfect. The idea of being in this chaotic and crazy city, laughing together just the two of us was an opportunity we couldn’t pass up.

What was the best part about getting to celebrate your wedding twice?

Everyone kept telling me that I would be really sad when it was over… but I wasn’t, because I knew I had a second one coming! Sydney was awesome and really felt like a celebration of the people who had been there for our near 10-year relationship. Our friendship group is so combined that it was really as much wanting to celebrate them, as it was about celebrating us.

Vegas, on the other hand, was this crazy, whirlwind experience. The best part is we have these incredible and intimate memories, which can harder to get at a bigger party. From getting ready together drinking champagne out of water glasses, to having a slice of pizza after our photos, it was the most special day that only we know about.

All in all, it was the best to be able to spend so many love-filled moments with Will. I don’t think we’ve ever had so much PDA in our lives, but it was a really special time that I know we’ll always look back on fondly.

Where were your dresses from, and what was the process of sourcing them?

I really wanted to focus on Australian designers for both the Sydney and Vegas looks. We have such incredible local talent, and it was really important to me to connect with that. I also wanted something that felt a little unconventional. I stalked hundreds of pages on TikTok and Pinterest of ‘cool brides’ until eventually my algorithm led me to a bunch of recommendations.

For Sydney, I was obsessed with Lola Varma. I worked with founder and designer, Courtney Illfield to style a look that I was and am still so in love with to this day. She styled me in a beautiful silk strapless top and long bubble skirt, which had this incredible sheer overlay that matched a hand-pulled silk shawl that I wore in place of a veil.

The layers and textures of the pieces moved beautifully, and the fact the skirt sat above floor length was something I knew I needed for dancing purposes. Will’s mum also kindly gave me one of his grandmothers gold bracelets to wear, which was a really special finishing piece.

For Vegas, I knew I wanted something fun and short, with a Pamela Anderson edge to it. I’d tried sourcing something vintage but couldn’t find a dress I loved, so pivoted to a white silk corset and skirt from Van Der Kooij, another Melbourne-based brand.

I was drawn to the off-shoulder neckline of the corset as it felt like a nod to the vintage element I was originally looking for, and the fact it was a set made it a lot easier to travel with. I paired this with a pair of white kitten heels from Magda Butrym (which I wore in Sydney as well), as well as white lace tights and a short white veil.

What about Will’s outfit?

Will’s suit was low-key the star of the show. He worked with Reigner, a Melbourne and Bali based label, to design a completely custom, embroidered, flared brown suit. The entire thing was filled with designs that he had come up with (with a little help from me), including native Australian flowers, margaritas, Aperols and our dog, Django, drawn to resemble a stain glass window design. The whole thing was finished with brown beading and bedazzling.

He also wore vintage cowboy boots that we sourced from Route 66 in Newtown, and he added a custom bolo tie featuring our dog for Vegas.

What kind of beauty and hair look did you go for on the day?

I wanted something super natural, glowy and bright, with a slick-back bun so my hair was out of my face. For Sydney, I worked with Alex Baek as my makeup artist. She made me feel like myself, just elevated.

For Vegas I learnt to do my own makeup, and while not as good as Alex’s work, I was still very happy with it. She gave me loads of tips and tricks so I felt confident going into it… despite nearly forgetting my eyelash glue (thank god for Uber Eats chemist delivery).

I was also lucky enough to work with The Clinic in Bondi Junction to make sure that my skin base was in its most optimal shape, and had a series of treatments over the year prior to the Sydney dinner to make sure I was glowing under my makeup.

What kind of food and entertainment did you have? And how did you choose the cake?

Food wise we did a three-course dinner and canapes. There were so many amazing dishes, including flatbread, steak and pasta. The staff and chefs were amazing, and joined us on the dancefloor at the end of the night.

Alongside the DJ, who mixed during the dinner and at the end of the night, we had a two-hour karaoke party instead of a band. Will and I spent the first few years of our relationship singing karaoke at our local pub every Friday night, so it only felt right.

We opened the session with a duet of ‘Kids’ by Robbie Williams and Kylie (I guess this could be considered our ‘first dance’), and had curated a list of songs from all our guests so that everyone could join in. It was so fun being able to see each of our friends or family take the stage, and I’ll never forget having my parents sing us ‘Love is in the Air’.

I’d really wanted to work with Valentine from Vege Mamma for ages, so our cake was an easy choice. I love the organic shapes and textures of her cakes. We briefed her to create a funky, blob of a cake with a few flowers and she delivered on just that. It couldn’t have been more perfect, not to mention delicious! The cake cutting was a highlight of the night for me. We played ‘Inner Smile’ by Texas at that moment, and as soon as the cake was cut, we had a little dance party and singalong.

Tell us about the photography – how did you capture each event?

For both events we leant into film photography. In Sydney we worked with Chelsee from The Golden Years, who was brilliant at snapping all the subtle, often unnoticed moments with our guests. We wanted to have a really candid approach to photography for the night so we could relive the essence of the evening.

For Vegas, we worked with Claudia from Petite Cherry Photo for the photoshoot of our dreams. We wanted it to feel fun and chaotic, like Las Vegas to the max. Claudia brought a sling of cameras, including a Super8 video cam. She sourced all the locations for us and helped us work with our vintage car driver to run around the city. We’re so obsessed with the photos, they capture how fun and happy the whole thing was and her direction made us feel super comfortable.

Did you have any other fun or unique quirks about your wedding?

In case it’s not obvious, we really wanted our longhaired dachshund Django to be a part of as much of the wedding as possible. He was the centre piece of our invites, and that same design (done by Bella from La Robe Club) was used across playing cards that we gave all our guests. Between the suit, the cards and Will’s bolo tie, we felt like we were able to have our littlest love present in as much of the day as possible.

I was also pretty certain about wanting some kind of bouquet for both events but wanted it to have a totally different look and feel. For Sydney, I worked with the amazing Claudia to create an arrangement that felt more like an accessory than a bouquet. I had briefed her on a handbag-style bouquet and she delivered beyond what I could’ve imagined. It was such a gorgeous freeform piece that I was easily able to carry all night.

For my Vegas bouquet, I worked with Lucid Juliet. It had a fun hanging piece at the bottom, and designers Haley and Erin used a beautiful long ribbon to tie it together, which felt like an accessory in itself.

How does it feel now, reflecting on both of your weddings?

I really recommend doing whatever you want for your wedding. Whether you want to ditch traditions or keep some (we kept speeches, for example), do what your heart desires. We had the best nights celebrating in a way that felt really true to who we are as a couple, and there is not a single thing I regret.

Find more from Kate here.