As you can imagine, meeting one of my fashion icons would be an amazing event even if I only had the opportunity to shake his hand so you can envision my excitement as I found myself suddenly in the limo bus with him, his beautiful step daughter, Eliza, who is the vice-president of the $250 million licensing department, and her husband, Alex Bolen, who is the company’s CEO.

I’m not one of those people who squeals around famous people having worked in the music industry for a brief (yet exhilarating) stint, I was able to meet some of the greats…and I can assure you, there was no squealing.  Meeting Mr. de la Renta was a bit different though his clothing and designs have always been a form of art that inspired me.  I have consistently been drawn to his designs if I am flipping through Vogue and suddenly go ooohhh,’ you can almost be certain that it is a de la Renta design.  So truth be told, I was completely overwhelmed in the limo bus of all places to be sitting with him, without any distractions and 20 minutes to ask him anything I wanted.  WOW.  (Let me thank Mr. Bolen for this opportunity. He so graciously invited me to ride with them to their private jet when he found out earlier that evening that I still had not yet had a chance to interview Mr. de la Renta.  He is a complete gentleman and extraordinary businessman).

Mr. de la Renta arrived two hours before the show that took place at the Nashville Schermerhorn Symphony, and at midnight was off again to New York to “work on the spring collection” for 2009 and can I add here that he looked as fresh and energetic as I imagine he would at 8am.When I asked him about why he chose to create a line of clothing for Macy’s, he answered, “(I design for) a woman who cannot afford to buy the expensive clothes now, but perhaps one day will be able to.”  He added, “Obviously, I try to create the same kind of clothes that I do for the expensive line. You know, I can only design clothes one way.  That is always doing the best that I can to make a woman look her very best.” The Oscar de la Renta woman is defined as elegant and sophisticated, and the Macy’s line exemplifies this statement.

When I asked if he had any tips for the everyday woman and by this I mean, not a celebrity…he quickly answered, “What is most important for a woman today is to express her own sense of individuality.  I say this is the best time, EVER, to be a designer because there’s never been in history a woman who is more in control of her destiny as a woman is today.  You know that a woman has a lot of choices.” He continues, “Obviously there is no loyalty among the consumer today, because what is most important is a projection of her own sense of individuality and an expression of femininity.  A woman knows today that even in the workplace to be a woman is a great asset.”

The purpose for the fashion show was to highlight his fall 2008 collection…which is truly exquisite.  To choose which glamorous piece of clothing actually makes it to the runway, he tells me it is a process of working with his assistants in his design studio.  The pieces that make it to the runway he feels are going to be the most commercial and will appeal to thebroadest group of women in the right price range.  He adds, “The dress has to merit being on the runway.”

Is there a deciding factor of why one dress is chosen over another?
“A part of it fulfills and represents something that I feel is very important to be part of the picture when I present the whole collection.”  When I ask if he has any favorites, he smiles and says, “I have no favorites, you know, I like them all.  Probably I like the one that nobody likes because I feel sorry for the dress.”

Running his business is truly a family affair. When I asked him if he enjoyed working with Alex and Eliza he said, “It is wonderful because I see a continuation of the brand which is important.  We are about building a brand and obviously having my family involved I know that it will continue and always be there.”  Alex Bolen, worked in finance, founding and then selling an asset-management company before joining Bear Stearns.  As the market stalled, Alex consulted part-time for De la Renta while the designer searched for a new CEO. “It took a very long time to convince Alex to work in the business.  Eliza has been working with me now for a very long time in the beginning she wanted to work in causes that had to do with the environment.  Eventually they decided that this was their business.”

With this new collection, is there ever a fear that it won’t be as good as or better than your last one?

“There is always a fear the day that you don’t have that fear then you should stop working.  Every day is a learning process, everyday.  People say, oh my goodness, you have been doing this for so many years, and you must have a sense of confidence with this collection.  No, every time is more difficult because you demand more of yourself.  Every time there are younger designers, new designers. Knowing that you have competition makes you try to excel and do your best.”

New designers are they really competition for you?

“Any business is a competitive business.”

Are there any major challenges that have come with the growth of this empire? (Fragrances, home goods, the Macy’s line etc)

“Every day is a challenge. The exciting part is to accept the challenge and then try to conquer the challenge.”

As we drive through downtown Nashville he takes a moment to look at Tootsie’s sign that is flashing at us…a few moments later he turns to me again and I ask him if he enjoys Nashville.

He grins and says, “Every time I come here it’s for a very short time, but to see downtown is exciting with all of the lights.”

Do you like country music?

“I love country music in the beginning not as much because I didn’t understand it.  My wife and I love Johnny Cash.  I never really paid any attention to Johnny cash until I saw Walk the Line.  Now we are big fans.”

What do you do to relax and find peace?

“I move on to something else.  I never stop moving. I’m involved in everything, so I take breaks by doing something different.”  He tells me about a project he is working on in his beloved home of Punta Cana.  He is invested in the the Punta Cana Resort & Club as well as the large ecological reserve to go along with it.  “My favorite place on earth is being with my family.  I don’t like to be alone, I like to be surrounded by people and the most important thing to me is to be able to share time with my family.  What I love most is really what I do on a daily basis which is to create clothes.  I don’t look at it as work I look at it as something that gives me tremendous pleasure.”

At the age of 18, he moved to Spain, where he studied painting at the Academy of San Fernando in Madrid.  He admits that his first love was painting and I wanted to know if he still enjoys picking up a brush.

“I am very competitive…If I were to be a painter I would want to be very good. It is pleasurable, but I would not do it if I could not compete and be the best at it.”

Words you hope to pass down to continue your legacy

“That I love the woman.”