An Iconic Portland Wedding at The Sentinel: Timeless & Luxe
There’s something undeniably magical about a wedding at The Sentinel in Portland, Oregon. The grand architecture, the timeless elegance, the way history seems to wrap around every moment—it’s the perfect setting for a love story like Jenna and Kai’s.
Jenna and Kai might call New York home now, but their hearts are rooted in Portland. They grew up here, so it made perfect sense to come back to celebrate the biggest day of their lives. Their wedding was a seamless blend of classic elegance and personal touches, bringing together the best of both worlds—the sophistication of New York and the warmth of their hometown.
Getting Ready at The Sentinel
The day began at The Sentinel, where Jenna had her makeup and hair done in the Fireside Room, surrounded by all of her closest ladies. The room was filled with laughter, excitement, and a few happy tears as the final touches were put in place. Once ready, she went up to the suite to slip into her gown from Ania Bridal with the help of her mom, sister, and grandma. The energy in the room was joyful, with just the right amount of wedding day excitement. As she slipped into her gown, you could see the emotions building—especially when she shared a private first look with her dad. There wasn’t a dry eye in the room.
Meanwhile, Kai and his wedding party were getting ready in their sleek black suits from Mr. Formal. The anticipation was palpable as he buttoned his jacket, preparing to see Jenna for the first time.
A Classic First Look and Sweet Tributes
Jenna and Kai chose the Renaissance Room for their first look—a breathtakingly empty space that felt like it was made just for them. As Jenna walked up to tap Kai on the shoulder, you could feel the weight of the moment. The way they looked at each other? Pure magic. We spent some time capturing portraits in the Renaissance Room before stepping outside for something extra special—taxi cab photos.
This wasn’t just a fun city moment; it was a heartfelt tribute to Jenna’s grandfather, who drove taxis for most of his life. The nostalgia and love behind those shots made them some of my favorites from the entire day.
A Ceremony at Holy Redeemer
After wedding party photos, we hopped onto a party bus and headed to Holy Redeemer for the ceremony. The wedding party looked effortlessly classy, all dressed in black, except for two special ladies who stood out in stunning blue ensembles. The ceremony itself was a beautiful, heartfelt celebration, filled with a classic catholic ceremony in the most gorgeous church.
An Elegant Reception in The Grand Ballroom
Back at The Sentinel, the Grand Ballroom was transformed into a vision of elegance. Flowers in Flight created stunning floral arrangements that brought the space to life, complementing the venue’s timeless charm. But Jenna and Kai didn’t just bring elegance—they also brought a little New York to the party. Instead of traditional late-night snacks, they served pretzels, popcorn, and hotdogs—a playful nod to their East Coast home. Guests absolutely loved it!
The Most Epic Grand Entrance & Millefoglie Cake Tradition
One of my absolute favorite moments? Jenna and Kai’s grand entrance. Instead of a typical introduction, they had all of their guests wave their napkins over their heads as they walked in. The energy was electric—it was the perfect way to kick off an unforgettable evening of dining, dancing, and celebration. With music by David Efaw Productions and Jafra Dabke Team, the dance floor was packed all night long.
Instead of a traditional cake cutting, Jenna and Kai opted for a millefoglie cake, a delicate and delicious Italian dessert. In a fun twist, they took part in the tradition of adding the powdered sugar themselves, making for a joyful and memorable moment that had guests cheering.
A Rainy-Day Twist & Flash Photography Fun
Halfway through the day, the Oregon rain made its grand entrance, meaning our planned sunset photos had to take a backseat. But honestly? It worked in our favor. We pivoted to indoor flash photography, and the results were nothing short of iconic. Think high-fashion, editorial vibes—proof that sometimes, a little unexpected weather can make for the most incredible photos.
The Perfect Blend of Classic & Personal
Jenna and Kai’s wedding was everything a wedding should be—timeless, deeply personal, and filled with love. From the elegant touches of The Sentinel to the heartfelt tributes woven throughout the day, it was a perfect reflection of who they are as a couple. It was an absolute honor to document their day, capturing moments they’ll look back on for years to come.