Our Engagement Photos!

Oh my goodness, you guys. I’m still so speechless over these photos that I have no idea how I’m going to write a whole blog post about this, but I need to try my best to share the magic with y’all. We’re completely over the moon with how this shoot turned out, and the images might as well have been pulled out of my dreams (but better). I have so much I want to say about how everything came together and how happy this day was, so buckle up – this is going to be a long one. 🥰

Let’s start at the beginning. I introduced my wonderful photographer and videographer on my Instagram stories the day of the shoot, but in case you missed it, we are thrilled to be working with husband + wife team, Ashley of Ashley Boyan Photography and Dustin of Thirty 1 Films! This was one of the most important steps for me in the wedding planning process, because when all the cake is eaten, the flowers have wilted, and the music has faded, your wedding photos and video are one of the only things that you’ll have forever. Ashley came highly recommended to me by one of Charlottesville’s best photographers, and when Will and I skimmed through her portfolio, we were immediately sold (specifically by this picture!). We really loved the idea of a husband + wife team for photography/videography so when Ashley mentioned that Dustin was a videographer, it all felt like it was meant to be. It also didn’t hurt that they were surprisingly affordable compared to some of the crazy prices in the area, not to mention we got a discount for booking them together!

Because we got engaged at the beginning of September, by the time we started thinking about our photos it was getting a little too chilly and dead outside. Plus, we knew our wedding photos were going to be during the peak of autumn, so we liked the idea of waiting until spring/summer so the photos could have a different vibe. The problem was, April showers led to more May showers, and finding a day that Ashley and Dustin could drive up to meet us, when they weren’t already booked for a wedding, when we could also get away from DC, and it wasn’t monsooning?? Not an easy feat. Oh, and did I mention it all had to be done by early June so I could get save the dates out with the recommended four month lead time? Luckily, these sweethearts were incredibly accommodating and easy to work with, so when the first date option was a wash (literally), they were able to give us two more right away to give us peace of mind. And guys, I cannot tell you how happy I am that we didn’t try to make that cold drizzly day work, because we were #blessed with the most insanely beautiful May evening.

For the first location, I had stumbled upon the scenic overlook called Raven’s Roost when researching engagement shoot spots around the area, and knew that had to be the winner. Growing up in Charlottesville, Will and I have always had a love for the mountains, and you just can’t beat that view. It’s only about 30 minutes outside of town, right off Skyline Drive on the Blue Ridge Parkway. I also knew I wanted to plaster all these photos up on our walls, so I wanted something that wasn’t too green-heavy, since the proposal was at a vineyard and the wedding will be at a cidery. Call me crazy, but yes these are the kinds of things I think about! 🙈 We timed it perfectly (thanks to Ashley and Dustin) so the sun was just starting to set when we got to the overlook, and couldn’t have asked for a dreamier moment.

For the second location…

For this location, I knew I wanted something neutral (with minimal green 😅), that wasn’t too far from Raven’s Roost, and a little more casual and lifestyle-y since the other was, well, a bit extra. I was completely stumped until my mom suggested Swannanoa, which is about 15-20 minutes from the overlook. For a quick history lesson, Swannanoa is an Italian Renaissance Revival villa that was built in 1912, partially based on buildings in Rome’s Villa Medici. Originally constructed as a “summer place” (cool cool yeah same) for Richmond-based millionaire/philanthropist James Dooley and his wife Sallie May Dooley, the mansion supposedly took eight years and more than 300 artisans to complete. K guys don’t scroll past, this is where it gets good. The intricate palace was actually built as a token of love from husband to wife, and featured lavish details like Georgian marble, Tiffany windows, gold fixtures, and terraced gardens – but the true depth of James and Sallie May’s relationship was represented in the 4,000 piece stained-glass window and a domed ceiling based off Sallie May herself. If that doesn’t set the stage for some romantic ass pics, I don’t know what does (yup sorry I ruined it, didn’t I).

Over the years, the mansion and surrounding property have become quite dilapidated, which is actually something we really loved. The marble edges are crumbling, vines have twisted their way around the structures, and wildflowers are sprinkled around the perimeter. I honestly think we would have felt too bougie in a completely pristine marble mansion, and the wild, messy feel made it a little more ~our vibe.~ Just FYI if you’re interested in shooting at the property, you have to pay a kind of annoying fee but since we didn’t have many other options for a nearby second location, we decided to just bite the bullet. And it was so worth it!

Now for my outfits… This was basically a final exam of sorts for a fashion blogger that used to work in the wedding industry! 😂 #TBT to my OG engagement photo outfit idea post circa 2014 🙂 When I was planning my looks, I had ideas of what I wanted, but it was just a matter of finding everything. With the help of my peeps and endless googling, I ordered a bunch of items that I thought might work, then tried them all on and took mirror pics. I’ve always wanted a flowy skirt and bodysuit or crop top for the dressy outfit so once I found the skirt (hit the jackpot here), it was just a matter of trying on some bodysuit/top options until I found the winner! For the casual outfit, I was feeling dark jeans and some kind of printed top, which was actually the most difficult to find. My main rule of thumb for these outfits (which still hold true from my vintage post almost five years ago) is to keep it as simple and classic as possible. Since I skew pretty trendy, I’m constantly cringing at outfits I wore even a year ago, and I never want to look back on this shoot and wonder what the hell I was wearing. If you share these sentiments, I think this is a great reminder for anything wedding-related – it’s totally fine to incorporate some trends here and there, but for the most part keep things relatively timeless.

As for Will, he actually has a really great sense of style so I fully encouraged him doing his own thing – with my minor feedback, hehe. I loved the idea of a plaid button down for the casual outfit (there’s just something about your man in plaid, amirite?), and I was super into the print mixing with corresponding colors in our outfits. For the dressier look, he took my vision and went with it, picking out a white shirt, a good pair of khakis, and his go-to boots. I originally wasn’t team blazer but then he put it on and I was like, yep you’re gorgeous and I know nothing. Isn’t he a snack, you guys?? 🤤

A lot of you have messaged me over the years when I share a cheesy pic and ask how on earth I convince Will to “cooperate.” Is it bribery? Is it manipulation? Is he just really that sweet? The answer, to all of the above, is no. For me, it’s all about some light conditioning and being selective about the moment. I realize all of this sounds silly, but enough of you have asked that I feel like I should share! For Valentine’s Day 2015, I asked if my present could be a fun shoot for the blog, and somehow he agreed. That Christmas, I lured him in again for a festive shoot with our photog friend featuring the pup, which I knew he couldn’t say no to. I think he felt comfortable with the low key photographers, quickly realized that it wasn’t as terrible and scary as he thought, and just saw how happy it made me. So that exposure helped a lot, but I also pick and choose when to be annoying about getting a cute pic. If I was asking all the time it would drive him crazy, but I try and save it for special moments. Then when it’s all said and done and the pain is over, he ends up thinking they’re cute too sooo he’s fine.

For our engagement session, it was a little different because I knew Will would feel a lot more pressure. We were planning to use these photos for our Save the Dates/wedding website/apartment walls, we didn’t know our photographers yet, and this step meant we were that much closer to the wedding. Because I could sense his nerves, I decided to do a little pep talk on the drive up the mountain. I told him that we should both think about things that make us really happy during the shoot so it truly captured us and our love – like the night we met on a back porch in 2009, how our dog smells like pancakes, the way our nephew exclusively refers to him as “Uncle Pee Pee Pants,” seeing his grandma all dressed up for the wedding, our first dance, and all our favorite people being in one room. I followed suit and went to our happy place during the shoot, and I think it really made a difference. To be fair, roughly half of the photos are a result of this, but for the other half I was just whispering sweet nothings about what we were going to eat immediately after the shoot (mostly Thai noodle related). Looking back at the photos you can see that we’re totally in our own world, and I really recommend doing something similar. One thing I was not prepared for, as I was not wearing waterproof mascara, was the newest happy place contribution by my future husband under the tree at the overlook – “our kids are going to see these.” Brb, crying. 😩

I also completely attribute how carefree and happy we are in these photos to Ashley and Dustin. We immediately felt a connection to them and their sense of humor, calming presence, and the fact that they’re major dog people (shoutout to good boy Endo, who was our hype man at the shoot). This helps tremendously in what can feel like a very overwhelming aspect of your wedding, especially if you’re not used to being in photos all the time, like my sociopath self 🙃 After about 2 min, they just felt like friends we had known for years, and there were lots of laughs and all around good vibes. I even told them they better keep partying with us at the reception even after they’re technically free to leave. Is it October yet?!

Outfit #2:
Top: Amazon | Jeans: J Brand | Wedges: Sole Society | Earrings: Nordstrom | Lip Gloss: NYX

Photos by the amazing Ashley Boyan Photography & Thirty 1 Films