Old Hollywood Wedding at Two of Palm Springs’ Classic Venues: Frank Sinatra Estate and O’Donnell House

When I tell you this was one of the most fun weddings I’ve been lucky enough to be a part of, I’m not joking. Ashley and Tim brought me out for the entire weekend, and as much as it was an absolute BLAST, we also got some of my favorite photos to date reminiscent of 1950’s Hollywood glamour. This old Hollywood wedding weekend all in all was one filled with incredible attention to detail, stunning locations, and unique entertainment.

How It Started 

From the moment Ashley reached out to me, I knew I wanted to work with her and Tim because of her genuine, vivacious spirit and how she drew me into their love story immediately. Ashley and Tim met via mutual friends while living in two different big cities (SF & LA). During their wedding toasts, we learned that Tim had a rule against dating outside of his immediate living area, but Ashley is easy to fall in love with and she swept him away to the bay area within a few short months. When you see them together… you see how giddy they are just looking at each other even after all these years. It’s one of the most beautiful parts of my job to capture that.

Ashely and Tim first came to me for their engagement photos which we took at Joshua Tree. If that day was any indication of how much fun we were going to have down the line, their Old Hollywood wedding weekend was sure to be a dream. While planning their wedding initially for 2020, Covid restrictions crept in and they unfortunately had to postpone the wedding for a full two years. Though,  in true Ashley and Tim fashion they couldn’t wait that long to share their lives together, so they hosted an intimate in-home civil ceremony in San Francisco via Zoom, and it was actually televised on the news! Check it out here! Due to travel restrictions, I *of course* couldn’t be there to snap pics… huge bummer, but these two truly captured the hearts of their whole city and mine from all the way down in SoCal. 

The Celebration of a Lifetime

Now when the time came to go big or go home, these two did not disappoint. They decided to host a welcome party the night before the wedding at none other than The Frank Sinatra Estate in Palm Springs. Leaning into the whole Old Hollywood wedding vibe, the place was THE PERFECT choice for a night-before gathering. The estate was fully equipped with old records, martinis, and some of the most gorgeous mid century furniture that exists.

Ashley and Tim wanted some extra time for photos together *a couple after my own heart*, so they decided to take some extra time to get ready and do a photoshoot before everyone got to the estate. This was so sweet, because it allowed them to have some time together before “having to be hosts” and we got some of the most special photos of the weekend. Once everyone did arrive, they got A SHOW. The most glamorous synchronized swimmers, The Aqualillies, gave an incredible performance  in the piano shaped pool, A Frank Sinatra impersonator sang his heart out for us throughout the whole evening, and they even had Tim’s step dad, who is a composer, playing and singing his own songs on the original piano that was in the house while Frank Sinatra lived there! They closed out their Old Hollywood wedding welcome party with an epic dance party, excited and SO ready to continue the fun the next day. 

The wedding took place at The O’Donnell House in Palm Springs, and transitioned from a fun “Old Hollywood wedding party” into a gorgeous Palm Springs outdoor, garden ceremony, and reception. We were surrounded by vibrant flowers, stunning mountain views and palm trees reaching the sky. While getting ready, Ashley and I got to make a super fun IG Reel showing off her gorgeous wedding gown. It was extra fun for me, because Ashley is the Co-Head of Product at Instagram, so to get to create with her in real time was an honor.

All in all, this was such a dream wedding to capture in photos and I can only hope they look back on these photos with love and happiness for years to come. You can also check out their wedding video by Rora Film Co here! You most likely will forget about a lot of small moments throughout the day, and even more so when you have multiple days of events. So if you have the means to bring your photographer out for the whole shindig, I obviously would recommend 10/10. 

 If these venues sound like they’re up your alley, check out my blog post on “The 5 Most Stylish Palm Springs Wedding Venues” and grab yourself some inspo! I swear Palm Springs is one of my favorite places to shoot and there are SO MANY good wedding venues there, so you’re going to want to check them out. And if you’re looking for a photographer who captures the heart and art behind your wedding day, let’s chat! 

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