I’m still dreaming about Amanda and Jacob’s vintage engagement session! Amanda came to me with a style that she wanted and we made it come to life!!! I absolutely love it when a couple’s vision becomes a stylish photo story that stands out. If you’re planning your own retro or vintage-style shoot, here’s how to nail the vibe with timeless charm and intentional styling.

CHOOSE AN ERA & LET IT GUIDE EVERY DECISION

Start by picking a vintage era that speaks to you as a couple. Amanda and Jacob leaned into retro energy, and this cute, old downtown—with its nostalgic storefronts and historic charm—was a perfect match. Whether it’s the refined elegance of the 1920s, the classic glamour of the 1950s, or the bold colors of the 1970s, defining an era will help you decide everything—from wardrobe and props to location and mood.

SCOUT LOCATIONS THAT ECHO YOUR THEME: THINK OLD FOR YOUR VINTAGE ENGAGEMENT SESSION

In my spare time, or every time I’m driving around, I am location scouting. That is just how my brain works. And I remembered that I had seen these cute old houses, just sitting next the the downtown. They were begging to be photographed, just waiting for the perfect session! This was it!!! The right backdrop elevates the vintage feel instantly. Look for settings with architectural or aesthetic details that echo your era—think vintage diners, retro storefronts, classic car garages, or even local streets with old-school vibes. These environments create context and texture for your story-driven session.

OUTFIT DETAILS THAT POP FOR YOUR VINTAGE ENGAGEMENT SESSION

Your wardrobe plays a major role in selling the vintage look. Here’s how to get it right:

Era-specific clothing: Think polka-dot dresses, retro suits, vintage silhouettes, or bold prints tailored to your chosen decade. Many times it is nice, and more understated, to take inspiration from these time periods rather than copying the style of the era.

This like this, if you are a Disney fan. Compared to Disney-bounding to wearing an actual costume.

Complement, don’t match: Choose outfits that harmonize in tone and texture so you look like a pair—but not identical twins.

Timeless over trendy: Opt for pieces with staying power so your photos still feel fresh years from now.

Deep textures and fabrics: Velvet, silk, or crisp cotton add visual depth—great for those moody retro images.

USE PROPS WISELY TO ADD STORY AND DEPTH TO YOUR VINTAGE ENGAGEMENT SESSION

In my opinion, in most cases, props are not necessary for your themed engagement session. Location and clothes are more important than props. I do think props can make an engagement session look cheesy or touristy and should be used with modestly. But…

Props offer visual storytelling and a way to feel natural in your photos. For that old-school shoot vibe, consider:

• Vintage cars or bicycles
• Old record players or vinyl records
• Retro café signage or neon light
• Checkered blankets, classic suitcases, or antique chairs

Just enough to add interest without clutter—think cinematic, not staged .

LET YOUR PERSONALITIES SHINE THROUGH

Posing doesn’t have to be stiff. The beauty of a retro-themed session is the chance to channel old-timey elegance with a modern twist. Here’s how:

• Play with motion—a spin in a circle, a walk down a sidewalk, a shared laugh.
• Go candid—moment caught while adjusting a tie or twirling a dress often feel more authentic than posed portraits.

I know what you are thinking: we are awkward in front of the camera. We can’t make this work.

YES YOU CAN!!!

You can get candid/documentary images even when you aren’t the most comfortable in front of the camera. The key:

Hire the right photographer!

Documentary-style photography is a LIE. It is all coached. 98.5% of the population would not be able to get images in that style without help.

A photographer that you are comfortable with and trust is a must!

ST. AUGUSTINE VINTAGE ENGAGEMENT SESSION

Are you planning a St. Augustine or Jacksonville wedding and are thinking of a vintage engagement session style? I would love to help you plan a session like this! An engagement session is included in every wedding day collection and comes with the FAMOUS Mollie Jane Engagement Session Guide! Hop on over to my website to check out all the information and send me a message. I can’t wait to talk to you!

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