An Honest Conversation with Chris Ocken and Dennis Lee
When the wedding day is over, the cake has been eaten, the flowers have faded and your gown has been carefully packed away, your photographs are what allow you to relive it all.
That is why photography should be one of the first vendors you book—and why choosing the right photographer requires more than scrolling through a few pretty Instagram grids.
On this episode of Martini Mondays with A.C.E., Alexandra was joined by Denise and two veteran Chicago wedding photographers, Chris Ocken and Dennis Lee, for an honest conversation about timeless photography, wedding-day timelines, bridal stylists, content creators and the one thing guaranteed to stress out your photographer: being late.
Meet Chris Ocken and Dennis Lee
Chris and Dennis have each spent decades behind the camera, bringing backgrounds in documentary photography and photojournalism to the wedding industry.
Dennis discovered photography after returning from a trip to North Africa and Spain with several rolls of, in his own words, absolutely terrible vacation photos. Instead of accepting defeat, he became determined to understand why the images did not reflect the incredible places he had experienced. He immersed himself in photography for four years, learning from accomplished photojournalists, presidential photographers and Pulitzer Prize winners before building his own career.
Chris began taking photographs in college for his school newspaper and yearbook. That eventually led to work with the Associated Press and opportunities to photograph political campaigns, including those of Bill Clinton, George W. Bush and John Kerry. After moving to Chicago and wanting to travel less as he built a family, he brought his journalistic eye into the wedding world.
Today, both photographers approach weddings with a documentary sensibility. Their goal is not simply to recreate a checklist of trendy images—it is to preserve the people, emotions and unexpected moments that make each wedding completely personal.
Your Wedding Photographs Become Part of Your Family History
A wedding gown may technically be worn for one day, but it lives on through photographs for generations.
The gown, the flowers, the venue, the architecture and even the way everyone is standing tell the story of a particular place and time. Years from now, your children and grandchildren may look through those images and see more than a beautiful wedding. They will see a piece of their family history.
Photography styles and fashion trends will naturally evolve. Film gave way to digital, and now couples are rediscovering film, Polaroids and other nostalgic formats. But while trends come full circle, the most meaningful photographs remain rooted in emotion.
The goal is to create images that still make you feel something 20, 30 or even 50 years later.
Before Looking for a Photographer, Look at Art
One of Dennis’s most interesting recommendations was to stop looking exclusively at wedding photography.
Pinterest, Instagram and TikTok can quickly fill your head with the same poses, locations and editing styles. When couples consume too many similar wedding images, it can become difficult to identify what they genuinely love—and even easier to accidentally plan photographs that look like everyone else’s.
Instead, look at art, fashion photography and beautifully filmed love stories. Pay attention to what draws you in.
Do you love images that feel romantic and softly composed? Are you more attracted to movement, architecture and dramatic lighting? Do you want polished editorial portraits, candid documentary moments or a blend of both?
Once you understand your visual preferences, you can search for a photographer whose work naturally reflects them. You will also be better prepared to explain what you want without asking someone to replicate another couple’s wedding.
Your photographer should capture your story—not simply recreate the photograph you saved from Pinterest.
Connection Matters Just as Much as the Portfolio
Your photographer will be with you for most of the wedding day—from the emotional getting-ready moments to the celebration on the dance floor. You need to feel comfortable around them.
A beautiful portfolio matters, but so does the connection you feel during the consultation. Your personalities, communication styles and expectations should align. If you feel rushed, pressured or uncomfortable before signing the contract, pay attention to that feeling.
Chris and Dennis also emphasized that photographers should be transparent about their availability. Couples deserve enough information to make an informed decision without being pushed into booking out of fear.
This is likely one of the largest photography investments you will ever make. Give yourself permission to ask questions and choose someone you trust to document such an emotional day.
Build a Photography Timeline—and Add Cushion
Your wedding timeline should include dedicated time for photographs, particularly portraits of you individually and as a couple.
Talk with your photographer about the people, locations and images that matter most. Put those priorities in order so that if something runs late, your photographer already knows what cannot be skipped.
Because something will almost always shift.
Hair and makeup may run behind. A family member might disappear at exactly the wrong moment. Transportation could be delayed. Weather can change. Five minutes here and ten minutes there can quickly eliminate 30 or 40 minutes of planned portrait time.
Experienced photographers prepare backup locations and alternate plans, but they cannot manufacture unlimited time. They can still create beautiful images during a shorter window—you simply may receive fewer of them, and everyone will feel more rushed.
The best solution? Build breathing room into the day and be honest about the people in your group who are chronically late. If your maid of honor has never arrived on time in her life, tell her she is needed an hour earlier. We say this with love…and experience.
Wedding-Day Stylists and Photographers Should Work as a Team
As bridal styling continues to grow, more couples want someone present throughout the day to keep the gown, veil, accessories and overall look photo-ready.
So, do photographers appreciate having a stylist there? According to Chris and Dennis, a good stylist can be incredibly helpful.
A wedding-day stylist can fluff the gown, reposition the veil, straighten a necklace or move a piece of hair before it becomes an issue in the photograph. This allows the photographer to remain focused on composition, light and emotion instead of repeatedly stepping away from the camera to adjust clothing.
The key is balance.
Not every wrinkle needs to be corrected, and not every strand of moving hair ruins a photograph. Some of the most beautiful images include movement, wind, confetti and wonderfully imperfect moments. A strong stylist understands when to step in, when to step back and how to work beside the photographer without interrupting the natural flow of the day.
The goal is collaboration—not a fight over who gets to fix the veil.
Content Creators vs. Photographers: Do You Need Both?
Wedding content creators provide something couples increasingly want: immediacy.
They capture short-form, behind-the-scenes footage designed to be shared quickly on Instagram, TikTok and other social platforms. If instant access and social sharing are important to you, a content creator can add a fun layer to your wedding-day coverage.
But content creation and professional photography serve different purposes.
A content creator provides quick, trend-driven clips. A photographer creates high-quality, carefully preserved images intended to become lasting heirlooms. One does not necessarily need to replace the other—but your professional photography should remain a priority.
Couples should also establish clear expectations among the photographer, videographer and content creator. Who has priority while you walk down the aisle? Who directs a portrait setup? Will someone holding a phone or stabilizer accidentally block the photographer during a once-in-a-lifetime moment?
These professionals can absolutely work together, but communication must happen before the wedding day. Otherwise, too many cameras competing for the same space can interfere with the very memories everyone was hired to capture.
The Biggest Wedding-Morning Stressor? Tardiness
When asked about the most common source of wedding-morning panic, Chris and Dennis immediately agreed: everyone being late.
Hair and makeup delays do not only affect the ceremony start time. They impact portraits, transportation, the venue, the officiant, the caterer and every other moving part of the day. Your ceremony may also be taking place at a church or venue with another event scheduled afterward.
Create a realistic timeline, add cushion and make sure every member of the wedding party understands when they must be dressed and ready—not merely when the ceremony begins.
And yes, this includes the friend who says, “Don’t worry, they won’t start without us.” Technically true. Still not helpful.
The Martini Mondays Takeaway
Your wedding photographer is not there to use your day as a backdrop for their own creative agenda. Their responsibility is to understand what matters to you, capture the emotions as they unfold and create photographs that allow you to experience those moments again.
Before booking your photographer:
- Explore art, fashion and films to identify the visual style you truly love.
- Review complete wedding galleries, not only a handful of Instagram highlights.
- Choose someone whose personality and communication style make you comfortable.
- Create a detailed photography timeline with extra breathing room.
- Prioritize meaningful people and locations over trendy, overused shots.
- Establish how your photographer, videographer, content creator and stylist will work together.
- And please—do everything in your power not to be late.
Trends will change. Social media platforms will evolve. But photographs that honestly capture your relationships, emotions and personal history will always matter.
A huge thank-you to Chris Ocken and Dennis Lee for sharing their experience, honesty and many years of wedding wisdom with Martini Mondays. Whether you are planning a wedding or documenting another important chapter of your life, these are two professionals who truly understand the difference between taking a pretty picture and preserving a moment.
Martini Mondays with A.C.E. is your source for unfiltered wedding and lifestyle advice—shaken, never stirred.
