Ben & Mary's Retro Drive-In Engagement Shoot | Hamilton Wedding Photographer / by Saharsh Cherian

I love working with couples who bring their own unique style and personality to their engagement sessions. Ben and Mary did just that during their recent retro drive-in engagement shoot, which was an absolute dream to photograph! Their session took place at a nostalgic drive-in theatre and included two distinct looks: one in vintage-inspired outfits with a classic car and another in comfy tracksuits at the retro arcade/diner attached to the theatre. I’m thrilled to be capturing their wedding next year, and this engagement shoot gave us so many amazing moments!

A Vintage-Inspired Engagement Shoot with Ben & Mary

For the first part of the shoot, Ben and Mary embraced the vintage vibe. Mary wore a stunning vintage dress, and Ben looked dapper in a classic suit. The setting—a retro drive-in theatre—gave us the perfect backdrop for capturing their elegant look. To make things even more perfect, we had a vintage car to complete the scene. The soft evening light at the drive-in added a nostalgic glow, making the photos feel like they came straight out of a classic Hollywood romance.

As a Hamilton wedding photographer, I know how important it is to create images that reflect a couple’s love story. Ben and Mary were naturals in front of the camera, and every shot told a part of their journey. From their playful interactions around the car to the more intimate, candid moments, we captured the essence of their love in a timeless way.

Fun and Playful: Tracksuits & Arcade Games

After capturing their vintage elegance, Ben and Mary did a quick outfit change into something more relaxed and fun: matching comfy tracksuits! We moved inside to the retro arcade and diner connected to the drive-in, where the couple had fun playing arcade games, sharing milkshakes, and enjoying the colorful neon lights.

This part of the session allowed us to capture their playful side in a more casual setting. The contrast between their glamorous vintage look and their laid-back tracksuit vibes was amazing, and it gave their photos a dynamic, storytelling feel. From arcade games to diner booths, the retro aesthetic brought out their fun-loving personalities, and it was a blast capturing these candid, energetic moments.

Why Choose a Hamilton Wedding Photographer for Your Engagement Shoot?

As a wedding photographer based in Hamilton, I love working with couples who want to incorporate unique and meaningful settings into their engagement shoots. Whether it’s a retro drive-in theatre, a scenic outdoor location, or a special place that reflects who you are as a couple, I strive to create images that are authentic and personal to your story. Ben and Mary’s engagement shoot is a perfect example of how incorporating a couple’s style and favorite activities can create truly memorable and visually stunning photos.

Looking Ahead to Ben & Mary's Wedding Day

Ben and Mary’s engagement session was one of the most fun and creative shoots I’ve had the pleasure of photographing. I can’t wait to continue telling their story next year when I photograph their wedding! As a Hamilton wedding photographer, it’s always an honor to be part of such special moments in a couple’s life, and I’m excited to see what’s in store for their big day.

the groom takes a selfie of his fiance kissing him in front of a retro car and drive in entrance

If you’re looking for a wedding photographer in Hamilton or the surrounding areas like Toronto, Burlington, or Niagara, I’d love to help capture your love story! Whether you’re planning an engagement shoot, wedding, or any special event, Pixelesque Photography is here to make sure your memories are preserved beautifully.