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An Old Hollywood Engagement Session at Jasper Bar in Richmond

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Caitlin Wilcox

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An intimate black-and-white portrait of an engaged couple at Jasper Bar in Richmond, VA. The groom lovingly holds the bride’s arm while she smiles, creating a tender and romantic moment captured in the cozy ambiance of the bar.

For couples seeking an elevated engagement session experience, the Jasper Bar in Richmond offers a unique and stylish setting that effortlessly bridges modern charm with vintage character. Kelly and Erik wanted their gallery to feel cinematic—more Old Hollywood glamour than traditional engagement session. With editorial inspiration, interactive elements, and intentional styling, their Richmond engagement session felt anything but ordinary.

We met at Jasper Bar on a quiet Sunday morning, before the bar opened. From the moment we stepped inside, the atmosphere was perfect. The moody lighting, leather seating, and marble tabletops gave the space an upscale speakeasy feel. Though the bar isn’t explicitly vintage, the way we approached this session—from lighting to composition to wardrobe—created a timeless aesthetic that fit their vision beautifully.

Why the Jasper Bar is a Standout Location for Richmond Engagement Sessions

It’s easy to see why the Jasper Bar made such an impact in this session. Even though Kelly and Erik had never visited the space before, it offered the perfect canvas for their vision. They were inspired by Old Hollywood and vintage bar scenes, and Jasper’s moody interior gave us the opportunity to play with flash photography, texture, and depth in a really fun way.

They brought unique glassware with etched mountain details, adding a small but thoughtful personal element to their session. While there wasn’t sentimental history tied to the location, it allowed them to enjoy the experience together in a relaxed, immersive environment that made their photos feel incredibly natural.

As a Richmond wedding photographer, I always tell my couples that the best sessions happen when they’re fully engaged in the moment—and bars like this offer great opportunities for that. Whether you’re sipping cocktails, leaning into the candlelight, or simply laughing across the table, interactive locations make posing feel effortless.

The Editorial Vision Behind This Richmond Engagement Session

Before the session, Devon and I created a mood board to help visualize the tone, lighting, and styling we wanted to bring into the space. This is a part of our creative process for every session and wedding we photograph. It allows us to plan intentionally while leaving space for spontaneity and real connection. For Kelly and Erik, the inspiration leaned heavily into vintage glamour—Old Hollywood portraits, classic cocktails, and film-forward artistry.

Their final gallery feels like a perfect extension of that vision. We incorporated 35mm film using a Canon 1V and direct flash for a nostalgic, editorial look. Many of the images captured at the bar counter, seated at the marble table, or framed within the glow of the moody interior feel like stills from a classic film.

If you’re looking for a space that allows for creativity while still feeling elevated and approachable, Jasper Bar in Richmond is a gem worth considering. It offers so much visual interest without needing elaborate props or posing.

Interactive Engagement Photos at Jasper Bar in Richmond VA

While some couples choose sentimental spaces for their engagement session, others—like Kelly and Erik—opt for something that simply feels fun. That decision can make all the difference. Having drinks in a cozy bar, leaning over a shared laugh, or toasting with a favorite glass allows couples to focus more on the moment and less on the camera.

This is part of why we love suggesting interactive spaces for Richmond engagement sessions. When you’re in an environment that invites movement, touch, and conversation, your connection shows through so clearly in the photos.

If you’re planning a session and aren’t sure where to go, let’s talk about locations like the Jasper Bar, or explore other creative settings around Richmond like the Quirk Hotel, the Virginia State Capitol, or other favorite spots in my Richmond engagement session location guide.

Your Richmond Engagement Session Should Feel as Good as It Looks

Kelly and Erik’s session was proof that editorial styling and authentic connection don’t have to be separate goals. Their gallery blends lifestyle, fashion-forward images with candid, joyful moments in a way that feels both elevated and personal. The atmosphere of the Jasper Bar, combined with their wardrobe choices, our direct flash and film approach, and their willingness to trust the process, made for a truly one-of-a-kind engagement session.

Whether you’re planning an intimate engagement session in Richmond or dreaming up your wedding day, I’d love to help you create images that feel timeless, artistic, and undeniably you.

If you’re looking for a wedding photographer in Richmond who brings both creativity and intention to every session, let’s start planning something beautiful together.

An engaged couple shares a romantic kiss at Jasper Bar in Richmond, VA. The bride wears a sleek white gown, while the groom is dressed in a classic tuxedo. The warm and intimate ambiance of the bar, with a tiger artwork and hanging plants in the background, adds to the charm of this moment.
An engaged couple shares a joyful kiss at Jasper Bar in Richmond, VA. The bride, wearing a simple yet elegant white dress, smiles brightly as her fiancé, dressed in a classic tuxedo, plants a kiss on her cheek. The intimate and stylish bar setting, with its dark wood accents and artwork in the background, adds a warm and romantic vibe to the moment.
A stylish engaged couple poses at Jasper Bar in Richmond, VA. The bride, wearing a simple yet elegant white dress, smiles at her fiancé as he gazes confidently at the camera. The groom is dressed in a sharp tuxedo with a bow tie. The intimate bar setting, with its vintage artwork and ambient lighting, creates a romantic atmosphere.
An engaged couple shares a celebratory toast at Jasper Bar in Richmond, VA. Their glasses, filled with a deep amber drink and garnished with cherries, clink together in front of a vintage bar shelf filled with liquor bottles. The couple's formal attire adds a sophisticated touch to the intimate moment.
A joyful couple shares an intimate moment at Jasper Bar in Richmond, VA. The man, dressed in a classic black tuxedo, lifts the woman, who is wearing a white, elegant dress, as they share a tender kiss. The rustic bar setting with shelves filled with liquor adds a cozy, intimate backdrop to this romantic scene.
An intimate black-and-white portrait of an engaged couple at Jasper Bar in Richmond, VA. The groom lovingly holds the bride’s arm while she smiles, creating a tender and romantic moment captured in the cozy ambiance of the bar.
A couple shares a tender moment at Jasper Bar in Richmond, VA. The woman, dressed in an elegant white gown, smiles as her partner, wearing a black tuxedo, gently kisses her shoulder while embracing her. The cozy, dimly lit atmosphere of the bar adds to the romantic feel of the moment.
A couple shares a playful moment at The Jasper bar in Richmond, VA. The woman, wearing a chic white dress and strappy heels, sits on the bar, while her partner, dressed in a tuxedo, kneels beside her with a loving gaze. The elegant bar backdrop features an assortment of liquor bottles, and the iconic 'The Jasper' sign completes the intimate setting.
A woman in a chic white dress sits on the bar at The Jasper in Richmond, VA, laughing with joy while holding a drink. Her white strappy heels and the elegant bar backdrop featuring shelves of liquor bottles and 'The Jasper' sign complete the stylish and fun atmosphere of their engagement session.
A woman in a white dress sits on the bar at The Jasper in Richmond, VA, enjoying a drink. The bar’s stylish decor, featuring rows of liquor bottles and modern lighting, creates a chic atmosphere for their engagement session.
A man in a tuxedo with suspenders and a bow tie leans against the bar at The Jasper in Richmond, VA. He holds his jacket over his shoulder, exuding confidence and elegance in the stylish bar setting with rows of liquor bottles in the background.
A man in a tuxedo with burgundy suspenders stands confidently at the bar in The Jasper, Richmond, holding a drink with a cocktail cherry. He gazes off into the distance, his jacket draped over one shoulder, exuding sophistication in the dimly lit bar.
A couple embraces in a close moment at The Jasper bar in Richmond, with the woman's head resting gently against her partner's. She wears a sleek white dress, and he sports a tuxedo with a bow tie, both sharing a quiet and intimate moment against the dimly lit backdrop.
A couple shares an intimate moment at The Jasper bar in Richmond, laughing and leaning close, their foreheads touching. The woman's white dress contrasts with the dark background, highlighted by soft lighting, creating a romantic and timeless feel.
A close-up of a couple's hands as they share a tender moment, dancing at The Jasper bar in Richmond. The man holds the woman's hand gently, both of them in formal attire, her white dress contrasting with his tuxedo.
A couple shares a tender dance moment at The Jasper bar in Richmond. The woman, wearing a white dress, looks lovingly at her fiancé, who is in a tuxedo. Their hands are intertwined, with soft lighting and elegant decor in the background.
A couple enjoys a relaxed moment at The Jasper bar in Richmond. The man, dressed in a white shirt and black suspenders, sits with a drink in hand, while the woman, in a white dress with strappy heels, playfully rests her leg on his lap. Laughter fills the air as they share an intimate and joyful moment together in front of the bar's shelves lined with bottles.
A close-up shot of the couple sharing a special moment at The Jasper bar in Richmond. Their hands are intertwined as they hold whiskey glasses, complete with orange peels and cherries, while the woman's legs are casually draped over his lap. The soft lighting of the bar creates an intimate atmosphere.
A tender, black-and-white close-up of the couple sharing a joyful moment at The Jasper Bar. The woman gently touches her fiancé's face, and they share a loving gaze, smiling in each other's presence.
A cozy moment between the couple seated at a booth in The Jasper Bar. They share a smile while holding their drinks, surrounded by lush plants and warm, inviting decor.
An intimate moment as the couple sits at the bar in The Jasper, sharing a drink. The man writes on a napkin while the woman smiles softly, her hand resting on the table next to a drink. The focus is on their hands, the napkin, and the drinks, captured in black and white.

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Meet Virginia
Wedding Photographers

Meet Virginia Wedding Photographers

Caitlin
and Devon

Caitlin and Devon Wilcox, a husband-and-wife photography duo, have captured the stories of over 200 joyful couples across the United States and Europe. Blending old-world artistry with modern techniques, they craft wedding galleries that are as authentic as they are timeless.

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