Jessica and Gavin are a couple who are madly in love and wanted their love captured through the little moments between them! We started their engagement session in The North End then headed to The Financial District for some playful parking garage photos! Their outfits were incredible and the right vibe for these city photos! Planning an outfit can be difficult especially when you don’t know where to start! So, before we jump into Jessica and Gavin engagement photos in Boston, I’ll be sharing some tips on what to wear for your engagement session!

What to Wear to Your Engagement Session

I am obsessed with the outfit choice Jessica and Gavin made for their engagement photos in Boston! Choosing the right outfit for your engagement session is crucial for capturing beautiful and timeless photos. Here are some tips on how to choose an engagement outfit.

Coordinate, Don’t Match

Choose outfits that complement each other in color and style without being overly matchy. Think about the location and choose colors that will stand out against the backdrop!

Accessorize Thoughtfully

Simple accessories can add a touch of elegance to your photos. Think scarves, hats, and statement jewelry, but avoid anything too distracting. For men, consider a nice watch or a stylish belt. For women, delicate earrings or a bracelet can add just the right amount of sparkle. You can even accessorize with a bouquet like Jessica did!

Comfort is Key

Wear something that makes you feel confident and comfortable. If you’re constantly adjusting your outfit, it will show in the photos. Choose outfits that you can move in easily, especially if you plan to sit, walk, or dance during your session!

Consider the Setting

Your outfit should match the vibe of the location. Casual clothes work well for a beach or park, while more formal attire is perfect for urban or historical settings. For a city session think chic and stylish! A cocktail dress or a sharp blazer like Jessica and Gavin’s outfits would be perfect!

Avoid Bold Patterns

Solid colors or subtle patterns photograph better than bold, busy prints. This keeps the focus on you rather than your clothes. Stripes, polka dots, and small florals can work well, but large, loud patterns might distract from the overall look.

Plan Ahead

Try on your outfits ahead of time and make sure they fit well. This gives you the chance to make any necessary adjustments and ensures you feel your best on the day of the shoot. It’s also a good idea to try sitting, standing, and walking in your outfits to ensure comfort and flexibility.

Bring Options

If you’re unsure about what to wear, bring a couple of outfit options to your session. Your photographer can help you decide which looks best with the setting and lighting. Having options also allows for a quick change to vary the look of your photos.

By keeping these tips in mind, you’ll ensure that your engagement photos are not only beautiful but also a true reflection of your style and personality!

Jessica and Gavin’s Love Story

Their journey began in 2015 at Springfield College, where they were both enrolled in the physician assistant program. By the end of their first year, a solid friendship had blossomed, continuing into their sophomore year. During their junior year, they took a tennis class together, and Gavin joined the campus activities board, a club Jessica had been active in since freshman year. That winter, their relationship deepened as they began texting and talking more. Gavin eventually asked Jessica out on their first date to Panera. Their senior year was a mix of easy classes and fun, but the graduate portion of their program soon began, bringing rigorous schedules and limited time for dates. Despite the challenges, they managed to balance their studies with their relationship and friendships.

They graduated in May 2021 and both secured jobs as physician assistants! With more free time, their relationship flourished, and in September 2022, they bought a home together. Gavin proposed less than two weeks later during a sunset on the beach in Punta Cana!  Even after five years, she feels like they’re still in the honeymoon phase, continuing to fall more in love with Gavin each year!

Jessica and Gavin’s Engagement Photos in the North End & The Financial District

North End

Jessica and Gavin’s engagement photos in Boston started in the North End. We met up for an evening sunset session. It was actually cloudy and foggy that day but the weather brought a romantic vibe to the session and we got to capture some really cool shots. Jessica and Gavin described themselves as beachy/coastal people so they really wanted to switch it up and add city vibes to their engagement photos in Boston. As the session began, we roamed around the neighborhood, and snapped pictures of them crossing the street, and walking throughout the cute streets of the town!

Their engagement session was a joy because they were open to anything I suggested, from outfit choices to locations. Jessica valued my input on her dress, bouquet, and even nail polish colors, which made the planning process smooth and collaborative. Their trust in my expertise allowed me to capture their genuine connection and personalities in a candid and authentic way throughout the engagement session! I loved their outfits! Jessica was wearing a white dress and Gavin was wearing a suit so it totally gave wedding vibes! They truly looked so sharp, fancy, and elegant. It was so cute how everyone kept complimenting them on how cute they looked for their engagement photos! 

Parking Garage Photos in The Financial District

After taking plenty of photos in the North End we headed to a rooftop parking garage in the financial district, which offered a stunning view of the iconic Custom House Tower. The empty rooftop was perfect for an uninterrupted photo session and we took advantage of that! We played Taylor Swift in the background, which Jessica loves and they danced along, popped a champagne bottle, and had fun with some black sunglasses for playful shots. The rooftop session was definitely a highlight, with the dramatic cityscape as a backdrop to their engagement photos in Boston!

What Jessica and Gavin had to say about their Engagement Photos in Boston

“I cannot say enough positive things about working with Bella! She will be shooting my wedding next year, and did our engagement photos in April. From our first consultation call, through each step in the process so far, Bella has been kind, knowledgeable, professional, and completely dedicated to her clients and business. We spent over an hour on that first call, and Bella explained her style, approach, and timelines.

As someone who knew nothing about wedding photography, I had plenty of questions and knowledge gaps. Bella took the time to address each one, and made me feel totally reassured. While planning our engagement session, Bella gave awesome recommendations and guidance regarding locations, outfits, and what to expect. When we met in person for that day, she was incredibly welcoming and warm. She made us comfortable in what might be an uncomfortable situation (because everyone runs around the North End on a Sunday taking pictures, right?!). Bella gave us cues and poses as needed, but she really captured our natural relationship/personalities in a way that felt candid and authentic.

When you work with Bella, you can tell that she not only is committed to her work, but that she honestly finds joy in what she’s doing. Bella knows her own style and work thoroughly, and she is upfront if she doesn’t think she’d be the right match for an event. I think, however, if anyone is looking for a photographer, you would be lucky to work with her! I am really grateful that she will be capturing our wedding.”

Book me for your Engagement Photos in Boston!

To all the engaged couples looking for a photographer for your engagement photos in Boston look no further! I would love to be a part of it and capture those candid and authentic moments for you! Fill out my contact form today!

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Romantic & Candid Engagement Photos in Boston 

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