New York City

Timeless New York Engagement Session


Carly and Jake, high school sweethearts turned lifelong partners, have a love story that’s as classic as New York City itself. They are each other’s best friend and 1000% in love which made capturing their iconic New York engagement session so much fun. From the charming streets of West Village to Madison Square Park and finally, The New York EDITION Hotel– this fashion-forward, love-filled session was one for the books.

Part 1: West Village

We started in the romantic West Village. If you haven’t strolled down these charming cobblestone streets or admired the timeless elegance of the Old Brownstones, you’re in for a treat! Carly, our soon-to-be bride, was absolutely radiant in her Cream Bouclé Mini Dress from Self Portrait, while Jake sported navy blue trousers paired with a stylish blue windowpane suit jacket.

As we meandered toward Greenwich, we fully embraced the New York City aesthetic – crosswalks, yellow cabs, graffiti-covered walls, and a quick pit stop at John’s Pizzeria on Bleecker Street. Carly and Jake indulged in some pizza curb-side and dressed to the nines – it was a whole vibe!

Check out this blog for more unique New York City engagement photo locations!

Modern engagement photos in West Village, New York City.
Modern engagement photo session in New York City.
Candid engagement photo shoot in New York.
West Village New York engagement pictures.
Documentary style engagement photography in New York.
New York City urban engagement photo session.
Documentary style couples engagement photography.
Romantic documentary style couples engagement photos.

Part 2: Madison Square Park

Flagging down a cab to Madison Square Park, Carly and Jake switched up their outfits, with Carly slipping into a chic black ruffled dress and Jake opting for a relaxed, neutral look. With a “city nightlife” atmosphere in mind, we strolled through the park, capturing their love under the sparkling cityscape.

Romantic nighttime engagement session in New York.
Romantic nighttime engagement session in Madison Square Park.

Part 3: New York EDITION Hotel

To wrap up our session, we landed at The New York EDITION Hotel on Madison Ave. By this stage, Jake had truly let his guard down, revealing the playful side of their relationship. We seized the opportunity to capture their intimate, playful side in the hotel elevator, turned the luggage cart into their own little playground, and, robes and all, fully embraced the hotel experience with pillow fights, room service, and plenty of cozy snuggling.

Creating Your Own Love Story

Carly and Jake’s New York engagement session was a mix of genuine moments and romantic backdrops. It’s a reminder that love can stand the test of time and remain fresh and vibrant. As you plan your own pre-wedding photoshoot, here are some playful tips to ensure it’s uniquely special:

  1. Choose Meaningful Locations: Consider locations that hold significance in your love story. Whether it’s where you first met or your go-to date spot, these places add an extra layer of sentiment to your photos.
  2. Mix Up Your Outfits: Changing your outfits during the session adds variety to your photos and can switch up the entire vibe of the shoot.
  3. Embrace Candid Moments: Embrace the spontaneous, unscripted moments. The best photos often come from those times when you’re just enjoying each other’s company, no planning needed!
  4. Include Your Favorite Activities: Like Carly and Jake’s pizza pit stop, bring in your favorite activities or hobbies. Whether it’s a shared hobby, a special meal, or just goofing around, it adds a personal, playful touch to your photos.
  5. Nighttime Shots: Don’t shy away from nighttime shots. The city transforms into something magical after dark, and these photos can be incredibly romantic.

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ABOUT Katherine

Born to a Cuban architect and an American history buff, I was raised with a passion for storytelling and an eye for the little details. 

I received my BA from Tufts University and was lucky enough to train in long-form narrative photojournalism under World Press Photo Chairman Gary Knight. While based in Rome working for the United Nations, I was hit by a car on my way home from work — what I call my “Regina George” moment.

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