Dr. Jennifer D. Dobbs’ A Fine & Dandy Affair™ Brings Glamour To Montgomery On The Road To Essence Fes

The mere mention of Montgomery, Alabama makes you stand up straight. It is a place that represents strength, change, and resilience. As the birthplace of the Civil Rights Movement, it is rich in the history of our people and therefore, deserves all the things. This year, Dr. Jennifer D. Dobbs,  Director of Cultural Affairs for the City of Montgomery, set out to create an event that brought a dose of dazzle to the beloved city. And thus, A Fine & Dandy Affair was born. What started as a gathering turned into an affair; hosted by Mya and a performance by R&B crooner Lloyd. Dr. Dobbs credits Essence with helping take the event up several notches. Thanks to their resources A Fine & Dandy Affair became a path way on the road to ESSENCE Festival of Culture®.

We caught up with Dr. Jennifer D. Dobbs ahead of the upcoming A Fine & Dandy Affair to talk about the event, the partnership with Essence and the Dandyism dress code.

A Fine & Dandy Affair

A Fine & Dandy Affair grew from a conversation with Mayor Steven L. Reed when Dr. Jennifer she asked him his vision for the cultural affairs department. His response was, to “raise the visibility of our arts and culture community.” Dr. Jennifer’s proverbial wheels started turning and she the idea for an event that encouraged the deserving people of Montgomery to dress up and celebrate, took shape.

“I thought at first, we’ll have a sort of gala event. And then I thought, we can’t have just an event to get dressed up for sake of having a good time. There has to be impact, there has to be meaning. How do we incorporate Montgomery into this? And then a light bulb went off. We need to focus on involving as many businesses and vendors, creatives, and influencers as possible. And so the idea came to mind isn’t there a catering program that can create art out of food? Doesn’t one of our colleges have a fashion department where we can involve the next generation of Dandy in this? We have so many good restaurants, you know, let’s have them be a part. Um, and, and so I thought this is an a gala. This is an affair, right?”

For Dr. Jennifer, the term affair has an “elevated touch.” It had such a ring to it, she trademarked it.

The Dress Code Is Dandy

Dr. Jennifer D. Dobbs appeared on our Zoom call in a jeweled tone silk blouse with tie adorned with a Queen pin. It was clear she considers herself a Dandy. And as a former clothier, she knows the importance of mixing and matching fabrics, patterns and colors.

According to Dr. Jennifer, Dandyism is a mindset. Dandyism’s roots date back to the 18th century. “Dandyism originally started with the aristocracy,” she stated. ” The sartorial style of dress shined as the 2025 Met Gala theme “Superfine: Tailoring Black Style.” With Montgomery’s Black history, it only made sense for Black folk to put on the best Dandy display.

“I have always been enamored with the male dress,” she explained. “Women, we have so many options to mix and match, but men have a sort of standard suit, right? It’s two piece or three piece. But I always liked how they are challenged to create their individuality with something as simple as a handkerchief or a brooch or their belt or the color of their socks. And how that is an expression of them and sometimes what they stand for. So really the inspiration behind it was that was men’s clothing. And knowing too, in the 1950s and sixties, and really in the beginning with the 18th century Dandyism originally started with the aristocracy. And it has slowly evolved to being something that even the every man can participate in. And so that’s what I thought would be a uniter is dandyism because it has a history, it has a modern interpretation, and not a lot of people are doing it. And then of course there are a lot of us who know about it. But the world really was introduced to Dandyism via the Met Gala last year.”

Last year’s Dandy-inspired Met Gala challenged celebrities and Hollywood elite to dig into their fashion bags to interpret the theme. “Listen, anybody can be a Dandy. She added, “Dandyism means impeccably quaffed. That means you are very thoughtful about your appearance and the message it gives. This is my opinion, Dandyism can express individuality, politics, rebellion, art, business. It’s a state of mind. So you have to have that state of mind. Because whoever is a Dandy, they have to know and understand that God made them and he’s perfect. So they’re perfectly made right, no matter who they are.”

Road To Essence Fest

Once A Fine & Dandy Affair caught its stride, Montgomery’s City Council Presdent and well-known consultants in the city of Montgomery connected Dr. Jennifer to the Essence team.

“And once we met, it was instant Love. We have the same energy, we have the same passion, we have the same, want to highlight us. To use their tag, we love us. It was very serendipitous meeting. I was talking through some things and then told them about A Fine & Dandy Affair, and I said, yes, this is going to be the inaugural year, and this is my vision for it, and this is how I see it in the future. And they were blown away. They said, oh my gosh, that is brilliant. We, we wish we had thought of that. And I said uh huh, it’s trademarked,” she said with a laugh.

“We decided let’s partner on that because it was exciting to them to be able to come in the ground floor with us on this effort. I have a vision to scale it and of course, they want to help set the foundation in order for it to be scaled, and they wanna be a part of this journey. On top of it, they said, you know what? We need to talk to Coca-Cola to see if Montgomery can be an official part of on the road to Essence Fest. And sure enough, that news came through and we were ecstatic. It’s a big deal. You know why? Because we are the only city this year that is a newbie to the National Series. So all eyes on us and Montgomery is deserving of that. So partnering with Essence, a very respected, time honored institution is such an honor and a blessing. It’s exciting. They come with so many ideas and resources that Montgomery may not have had access to. And so this is a very win-win celebration of partnership and of us.

A Fine & Dandy Affair kicks off May 15–17, 2026, as part of the official Road to ESSENCE Festival of Culture®.