The Oaklander Hotel Engagement

If you’re dreaming of a classy and romantic hotel engagement in one of the best hotels in Pittsburgh, the Oaklander might be the right option.

There’s something incredibly special about photographing a love story in a place that feels like it could be out of a movie: Timeless, luxurious, and filled with ambiance.

That’s exactly what it felt like when I photographed this romantic engagement at The Oaklander Hotel, Autograph Collection in the heart of Pittsburgh’s Oakland neighborhood.

Whether you’re planning a chic engagement session, a date-night-inspired photo shoot, or even a romantic anniversary celebration, this hotel offers the perfect backdrop for a sophisticated and editorial-style session with so much variety.

Why Choose The Oaklander Hotel for Your Romantic Engagement Session?

The Oaklander is truly one of the best hotels in Pittsburgh—not only because of its luxury and style, but because of its vibe.

It’s intimate, elegant, and perfectly nestled among some of Pittsburgh’s most iconic landmarks like the University of Pittsburgh, Carnegie Museum of Art, and the Cathedral of Learning.

You’re getting charm, art, architecture, and urban energy all in one place.

As a Pittsburgh-based documentary and editorial photographer, I always look for locations that allow for variety and storytelling.

The Oaklander Hotel is a dream for that.

Inside the Session: From Lobby to Rooftop

We began in the lobby, which immediately gave off moody, high-end cocktail lounge vibes.

The lighting is soft and ambient, and the interior design mixes modern touches with warm tones.

The couple sipped cocktails, and we captured relaxed, intimate moments in the plush lounge seating.

Then we moved to the bar area, where the mood shifted into something sexier and bolder.

The bar at Spirits & Tales (located on the 10th floor) is known for its amazing craft cocktails and floor-to-ceiling windows overlooking Oakland.

It gave us a stunning view of the city and a romantic cloudy vibe that is so unique to Pittsburgh.

The couple cozied up on the bar stools, clinked glasses, and laughed over shared drinks.

The Oaklander Patio calls for Intimacy

Next stop?

The Oaklander Hotel patio.

There’s nothing quite like a rooftop photo with the Pittsburgh skyline subtly in the background.

The outdoor terrace gave us room to play with movement.

Lots of twirls, champagne pops, and those wind-in-your-hair moments that always feel spontaneous and real.

Doing Photos Outside of Oakland in Pittsburgh

We took a walk outside the hotel to capture the energy of the Oakland neighborhood itself.

The perfect way to end this part of their engagement session was with the Cathedral of Learning in the background

The urban mix of classic architecture and the buzz of the city gave our photos an extra layer of energy and romance.

Benefits of Booking a Hotel Session

If you’ve never considered doing a romantic engagement in a hotel setting, here are a few reasons why it might be the perfect fit for you:

• Privacy & Intimacy: Hotels like The Oaklander offer cozy nooks, dim lighting, and that exclusive feel where you can just be together.
• Style & Ambiance: The curated design and upscale décor elevate your photos immediately
• Weather-Proof Options: Rain or snow? No problem. You’ve got indoor and covered outdoor spaces that photograph beautifully.
• Date Night Feel: You can turn your photo session into an actual date. Start with drinks or dinner at the rooftop bar, get dressed up, and make the whole experience feel effortless and fun.
• Location Variety: From modern interiors to outdoor scenes and architectural surroundings, you’ll get so much visual variety without needing to hop around to multiple locations.

Planning Your Own Romantic Engagement at The Oaklander Hotel

What to wear for your Oaklander Engagement Session

If you’re considering a romantic photo shoot here, wether an engagement or an anniversary session, I recommend wearing something sleek and elegant.

A silky dress, a suit jacket, or even something playful like a little white dress and heels can completely elevate the vibe.

Don’t be afraid to bring a bottle of champagne, your favorite pair of sunglasses.

Anything that makes the session more personal and you, is a great add on for your engagaement.

We will use flash photography for a high-fashion look. It will add that Old Hollywood flair to it, which will give you plenty of variety in your gallery.

Planning a Romantic Engagement Session with Natalia Baqueiro

If this sounds like the kind of session you’ve been dreaming of, let’s bring it to life!

Whether it’s a pre-wedding shoot, an engagement, an anniversary session, or just because you want to capture this moment in your love story, The Oaklander Hotel is one of my favorite spots to create magic in the city.

Reach out and let’s plan your Lover’s Experience together.

Booking Natalia Baqueiro as your wedding photographer

If you’re planning a surprised wedding proposal, or an engagement session and you want an experience of a lifetime.

Make sure to send me an inquiry so we can start crafting the right experience for you!

If you’d like to plan for your Pittsburgh Courthouse Elopement, you can also check out this article to make it easier and if you need ideas for your city elopement.

Some wedding collections include an engagement session. Find out more information about the packages and collections Natalia Baqueiro Photography offer for wedding photography.

If you need more inspiration when it comes to locations, here’s two guides on the most Iconic Pittsburgh Locations in the Steel City and the Best Pittsburgh Engagement Locations to consider so you can get more ideas on what vibe you’d like.