Philadelphia Engagement Photos – Mad Med Style – Stephanie & Rich

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Steph and Rich are huge Mad Men fans, so we used that for their GTKY session theme. As we have all of our couples do for GTKY sessions, they sent us their outfits before we met with them. We knew that they were going to look great based off of the images we saw, but it was so cool to see them all dressed up in person! The perfect spot in Philly for their session was around Old City and Penn’s Landing. We always find so many different places to create in that area, and this was no exception. Steph traversed cobblestone and busted brick alleyways in heels just to get the perfect photographs. We took a pizza break (our favorite) while we waited for the light to fade to get the nighttime portion of our session in. Strung lights out on Market Street were perfect for this! Another great thing about Philly is that there are open grates with air flowing up onto the street, which is ideal for old school Marilyn-Monroe-dress type photographs.

About Old City and Penn’s Landing

Old City sits inside the most historic square mile in America. William Penn stepped ashore at what is now Penn’s Landing in 1682, Ben Franklin walked these blocks, and Elfreth’s Alley, just off 2nd Street, has been lived in continuously since the early 1700s, making it one of the oldest residential streets in the country. For photographers, all that history translates into texture: cobblestones, brick alleyways, shuttered windows, iron railings, and the waterfront a few blocks east. It is also one of the few neighborhoods in Philadelphia where a vintage wardrobe does not look like a costume. It looks like it belongs.

Mad Men Style in Old City

Styling makes or breaks a themed session, and Steph and Rich nailed it, polished, tailored, and straight out of the Sterling Cooper era. We scouted spots to match: plain brick walls, old doorways, and blocks without a modern storefront in sight, so every frame feels like a still from the show. When the wardrobe is right, sixty year old architecture does half the work for you. The two of them committed to the bit all evening, and it shows in every photograph.
Stephanie and Rich's Mad Men style engagement session in Old CityMad Men themed engagement portraits in PhiladelphiaStephanie and Rich in vintage style on the cobblestones of Old CityRetro engagement session photographs in PhiladelphiaStephanie and Rich's vintage engagement portraits at Penn's LandingPhotobomb moment during Stephanie and Rich's Philadelphia engagement session
Photobombed!

Night Photographs on Market Street

Once the light faded, the session got even better. The strung lights over Market Street gave us a warm, glowing backdrop you cannot fake, and the evening crowd thinned out enough to let us work the middle of the block. This is why I love building a pizza break into a session. You rest your feet, you let the sky go dark, and you come back with a completely different set of photographs from the same few blocks. Two sessions for the price of one.
Stephanie and Rich's Mad Men inspired engagement portraits in PhiladelphiaVintage style engagement photographs in Old City PhiladelphiaStephanie and Rich on the streets of Old City PhiladelphiaRetro styled engagement session in PhiladelphiaStephanie and Rich's engagement portraits near Penn's LandingMad Men themed couple portraits in PhiladelphiaStephanie and Rich exploring Old City during their sessionClassic style engagement photographs in PhiladelphiaStephanie and Rich's GTKY session in Old CityPhiladelphia engagement session with vintage stylingStephanie and Rich under the string lights on Market StreetNight engagement photographs in Old City PhiladelphiaStephanie and Rich dressed to the nines in PhiladelphiaEngagement portraits on the cobblestones of Old CityStephanie and Rich's Philadelphia engagement session after dark

Why a Themed GTKY Session Works

GTKY stands for Get To Know You, and it is the heart of how we approach engagement sessions. Give a couple a theme they genuinely love and the nerves disappear, because they stop performing for a camera and start playing characters together. Steph and Rich spent the evening laughing instead of posing, and that energy is exactly what shows up in the final photographs. By the time their wedding day arrived, working with us felt like hanging out with friends who happen to carry cameras.

A few pointers if you want to try a themed session of your own. Pick an era or a story you both already love, not one that photographs well on Pinterest. Send us your outfits ahead of time, the way Steph and Rich did, so we can scout locations that match. And plan for a break in the middle. The best frames of this session came after dark, after pizza, when both of them had forgotten the camera was there.

Planning a Philadelphia Engagement Session?

Old City and Penn’s Landing top my list of Philadelphia session spots, but the city is loaded with neighborhoods that photograph beautifully, from the murals of South Philly to the gardens of Fairmount Park. If your wedding planning is still in the venue stage, my guide to the best Philadelphia wedding venues walks through the spaces I photograph most, with notes on light, logistics, and the portrait spots near each one. Bring your theme, bring your dog, bring your appetite for pizza. We will handle the rest.

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