Casual Engagement Photos on Historic Market Street || Ana and Will
I had the best time meeting up with Ana and Will for their casual engagement photos on Historic Market Street this past spring, and I am absolutely obsessed over the quintessential charm of their photoshoot.
Literally nothing about their session went according to plan (more on this below 🤣), and yet I still called Jon on my way home, “Everything about today was perfect.” They showed up like champs and had the absolute best attitudes, and even though we ended up meeting up in the middle of a (literal) chill, our session was still filled with so much warmth, laughter, and playfulness.
Hi, I’m Emilee
If you’re looking for joyful, artful, emotion-rich imagery, then I maaaay be your gal!
I’m an Upstate NY Wedding Photographer who specializes in a laid-back photography approach, and I’d love to help tell your love story!
During our photoshoot, I was able to learn more about Ana and Will’s connection— that they are super involved in their church, love spending time with family, are obsessed with all-things sports, and that Will in particular is a die-hard Yankees fan (which left us with no shortage of things to talk about since my husband and I bleed orange and blue, and Juan Soto had just been traded to the Mets 🤣). Best of all, I learned more about how their faith has been/is such a huge part of their love story!
“You're a Christian photographer,” Ana said to me, “and to most people that probably wouldn't matter, but I feel that because we share the same faith and love for Christ, that there will be a different dimension of beauty portrayed and an added layer to these images that showcase our love for each other.”
Say less, my girl. 🙌🏼 I could NOT agree any more, and from the moment that Ana, Will, and I actually met, it was more than an instantaneous friendship— it was like uncovering this deep, spiritual bond, one that was rooted in the love of God and unified through Christ.
Trevin Wax talks about how this type of Christian unity is ultimately an echo of what God is like, a reflection of the Trinity, and a way of participating in the oneness of the triune God.
I felt that to be such a sweet reality with Ana and Will. Even though we had never met in person prior to their engagement shoot (or honestly known each other longer than a hot minute 😂), our bond was so rich that it was a true testament to God’s salvation and redemptive work in the Church.
Throughout the course of our photoshoot, Ana and Will shared with me how they serve at their local youth group at church and how they’re especially excited to grow in Christ together through marriage.
“We both feel called to pastor people and cannot wait to begin that journey together— lifting each other up, sharpening one another, and sharing in the love of Christ,” Ana said.
Jared Kenndy speaks to this concept of viewing marriage as a “missional partnership,” and I was so encouraged hearing Ana and Will talk firsthand about their passion for this. 🥹
We shared so many amazing conversations and gut-busting laughs, and looking at their photos alone, you might think we met up for engagement photos on a mild, springlike day, felt the warmth of a sunkissed breeze, and scored the perfect photoshoot conditions.
But in all actuality, we landed a brutal March afternoon with a high of 49°F, wind gusts that were up to 30 mph, and a wind-chill that felt more like below-freezing. 🤣
Psst… in case you haven’t noticed, awkward photos aren’t really my vibe.
My goal is to get you feeling comfortable and yourself, so you can enjoy personality-driven imagery for years to come!
If you’re looking at this gallery, thinking, “YASSSSS!”, then we need to talk… like yesterday!
Keep scrolling to see Ana and Will’s full engagement gallery ↓
We started planning their engagement session with a vision for a romantic, secret garden vibe in the heart of springtime, the idea being— engagement photos that teemed with lush greenery, rich florals, and a springtime glow.
But as calendars shifted and Ana and Will faced some scheduling conflicts, we bumped the session up to mid-March. (Spoiler alert: that’s not quite springtime in these parts. 🤣) The day of their engagement photos turned out to be a classic Upstate cocktail— cold, windy, and somewhere between mist and rain. It was the kind of day that chills you to the bone. But they showed up so solidly anyway. ✨
Ana and Will drove all the way from New Jersey, where the temperatures were teasing something mild and sweet— definitely at least 10 degrees warmer than what greeted them here in the Finger Lakes region.
We were all underdressed (though at least they had a good reason why, whereas I was just being foolish.🤣), we were all cold, and yet, we all just rolled with the punches! We leaned into casual, playful vibes, and that became the energy of the day… go with it, have fun with it, and embrace the imperfect charm of early (glacial) spring in a historic town that knows how to wear its weather well.
We shot their session in one of my favorite corners of the world— historic Market Street in Corning, NY. Market Street is an old, brick-laced downtown in Upstate New York that feels like it’s been plucked from a Hallmark movie and dusted with real life. Think cobblestone alleys, weathered storefronts with antique signs, ivy climbing up stone walls, and lampposts that flicker on just as the light dips.
This location was such a scenic, idyllic setting for a romance as wholesome as Ana and Will’s, where every creaky doorway and fogged-over window added just the right amount of character to their engagement shoot.
The charm wasn’t just in the architecture and history of the street alone— it was in this quiet, invitation-like offer to slow down, look around, and enjoy the picturesque scenery of Upstate NY. For Ana and Will who love the simple and sweet things in life, this engagement shoot location seemed like the perfect, most personal spot for their vibe.
We wandered through narrow alleyways, ducked under awnings to hide from bursts of wind, and when it became too cold to bear, stopped to warm up (and indulge 👀) at my favorite ice cream shop, Dippity Do Dah’s.
Every moment felt spontaneous, like we were just taking a stroll— old friends catching up and enjoying time together in the most down-to-earth way possible— camera in hand, minus the pressure and stiff poses. It honestly was as if they were on a date, so relaxed and laidback, and I loved watching them savor each other’s company.
This is one of the things I love most about engagement photos— creating an environment where you feel relaxed, present, and completely yourself!
It’s my desire to truly get to know each of my couples on a personal level, create imagery that feels joyful, artful, and personality-driven, and celebrate their upcoming marriage in an honest way. That kind of storytelling only happens when there’s a real connection between us, one in which we feel comfortable with each other! I aspire to cultivate this type of genuine friendship with every one of my couples so that I can create the most meaningful, emotion-rich imagery. (Psst…read more about my full photography experience here!)
This was 100% the vibe with Ana and Will.
Casual engagement photos for days, free-flowing prompts, and organic interactions between one another in a way I can imagine them always doing— talking with their hands, playfully nudging into one another, and exchanging sweet, goofy glances that tell you everything without saying a word. Their session felt like a unique, firsthand peek into their world, just me and camera in tow, and I was obsessed with how playful and care-free our time was together. Ana and Will didn’t overthink it, and in turn, I was able to tell their love story in the most genuine way.
If you’ve ever felt unsure about what to do or how to plan for your engagement shoot, let this be your sign— the best photos happen when you wholeheartedly trust your photographer!
Through a foundation of mutual trust, I was able to guide Ana and Will through a series of interactive prompts and poses that resulted in dancing under the street lights (talk about a scene out of the Notebook!), racing down the sidewalk like a couple of schoolkids, and embracing the wind and weather like it was all part of the adventure. Their session became less about looking perfect, and more about feeling real— and in doing so, was impossibly joyful, unfiltered, and cozy.
Ana selected casual engagement shoot outfits for their session, leaning into soothing and neutral tones that complemented the changing seasons.
She kept it classic with an ensemble that whispered of spring (even if the temps didn’t agree 👀)— a jean jacket over a floral maxi dress and classic white Reeboks— and Will coordinated with dark, minimalist layers and Reeboks to match. Ana and Will’s outfits were the perfect choice against the soft grays and deep reds of Market Street’s old-soul buildings, the muted blues of the overcast sky, and the twinkling lights wrapped around the surrounding trees, and I loved that they were less matchy-matchy and more of a great color combo instead. Best of all, it was a total reflection of Ana and Will’s laid-back, down-to-earth relationship.
There was such a soft ambiance to their entire shoot, and between the casual engagement shoot outfits and the warm halo effect of the twinkling lights, the entire street turned into something out of a storybook— part old-world charm, part modern fairytale.
All in all, their look felt grounded, light and fresh, and a nod to the season we wished it was. But word to the wise— lessons were learned from their engagement shoot. 🥲
Hear, hear couples interested in springtime engagement photos in Upstate NY— even when it looks like it’s going to be warm and springlike or if the forecast calls for gorgeous sun, mild skies, and a gentle breeze— the Finger Lakes region doesn’t care what we have on our calendar. 🙃 It will do what it pleases. And your engagement session? It might be sunny. Or cold. Or windy. Or bone-chilling. But that doesn’t mean it still won’t be beautiful!
Here are a few tips for embracing whatever weather is thrown your way for your upcoming spring engagement shoot— or for that matter, your winter engagement photos. 😆
Layer, Layer, Layer: It’s so much easier to shed a jacket or scarf than to pretend you're not freezing in a summer dress. 🙈 Warm layers = longer stamina and more fun!
Dress for the Forecast… then subtract 10°F: Choose outfits that look good, but also will feel good if the elements take a turn for the worse. If it’s already slated to be cold, think cozy layers, stylish coats, and boots that will keep your toes from freezing off!
Plan a Warm-Up Break: Together, let's map out a cozy coffee shop or book store where we can pause, regroup, and (quite literally) thaw out. Because honestly, these indoor moments turn into the best conversations— and sometimes even the most intimate photos from the entire session. (Peep Nicole and Truett’s charming engagement session in historic Franklin, Tennessee where we pulled out all the stops all at cream parlors, book stores, and all the window shopping a girl could dream of!)
Ana and Will’s casual engagement photos definitely didn’t turn out like we expected, and despite all the shivering, their session turned into a version of beauty that wasn’t curated, but rather— real, raw and unscripted.
The quirks, the weather, the snorts of laughter, and the wind-blown hair— it reminded me of the kind of authentic storytelling that doesn’t require ideal conditions as a prerequisite. Just two people who are in it together, laugh when it rains, hold hands when the wind blows hard, and show up even when it’s difficult (cold noses and all).
Honestly, my time with Ana and Will was an honest, accurate glimpse of marriage itself.
Romans 3:23 states that “all have sinned and fallen short of the glory of God” (ESV)— which of course applies to the ones whom we love, choose, and marry! Dr. Tammy Smith shared in a recent Hosanna Revival article how it’s common that,
“We expect our marriages to be one way; they are not. We expect our spouses to be certain ways and do certain things; they are not. We expect a marriage made before God in true union with him to not be so hard or heavy; it is.”
Such has been the case in my own marriage, and speaking candidly, such is the case in all marriages— everyone is broken this side of heaven, and our ultimate fulfillment won’t come from our spouse, but from God alone!
Paraphrased from Timothy Keller’s The Meaning of Marriage (a book that radically transformed my perspective on marriage):
“The experience of marriage will unveil the beauty and depths of the Gospel; it shows that, though we are more sinful and flawed in ourselves than we ever dared believe, we at the very same time are more loved and accepted in Jesus Christ more than we ever dared hope. The Gospel can fill our hearts with God’s love so that we can handle it when our spouse fails to love us as he or she should, and it frees us to see our spouse’s sins and flaws to the bottom – and yet still love and accept our spouse fully.”
Marriage reveals our shortcomings completely, yet simultaneously points us to the Gospel and gives us a blueprint for loving, choosing, and cherishing our spouse— no matter what curveballs (or unexpected cold snaps) are thrown our way!
Ana and Will, thank you for braving the chill with me, showing up with unapologetic joy, and letting me be the one to tell your love story in such an honest, heartfelt way.
I can’t wait to see how beautiful your wedding is, knowing that it’s sure to be as magical as these playful, casual engagement photos— but for everyone’s sake, hopefully it’s just a few degrees warmer. 😆 Cheering you on in all-things life, marriage, church ministry, and the Gospel (just not on the diamond. 👀) Love you both long-time!