The Good Life
with a Southern Drawl

Woman Of Style Kimberly Kennedy

By Amy Bailey — November 21, 2014

Kimberly Kennedy is a guru in living beautifully. From entertaining to cooking to even building a house, she is not afraid to dive right in, get her hands dirty, make mistakes along the way, and learn how to do something well. This lifestyle expert and master entertainer also offers tremendous wisdom any woman could learn from. We hope her words encourage you and inspire you.

What is your favorite part about waking up in the morning? In general, I am not a coffee drinker nor a morning person, but I do love waking up with my dog Sadie every morning. She is a 14 year old Yorkie and has slept in our bed since she was a puppy. She loves to sleep in as much as I do and she’s like a warm fluffy blanket beckoning me to stay in bed just a little longer. To me, there really is nothing as comforting as snuggling with her before I start my day.

What inspires you each day? As a creative person, I tend to find inspiration everywhere. In general, I am drawn to details. Because of this, different cultures fascinate me. I love travel and try to live like a local wherever we go – soaking up all the subtle nuances. I am inspired by the big picture travel provides as well as the tiniest cultural details I find while abroad. Details, details, details. Love them.

How does your home and family inspire you? My son, Spencer, is an endless source of inspiration. I love his observations and young perspective. It’s fresh and helps me look at everyday things differently. My husband and I are constantly making things together. We love to cook, create in the woodshop, or expand our garden. We live by the philosophy that -instead of purchasing- we can make anything we want and we enjoy the process from design to building. We built our home with our own hands 15 years ago. It is filled with fun memories and serves a constant reminder that we really can create anything we put our minds and hands to.

What is your favorite thing about calling the South ‘home’? Having gone to school in the New York until the age of 13, I am keenly aware of what is uniquely Southern and I love too many things about the South to have one favorite. It has been my home for a long time and I honestly can’t remember it any other way. I would say I most appreciate the hospitality you find in the South. I love how everyone has a story and they are willing to share it with you- be it through words, food, arts, architecture. There’s an open door policy the South embraces where nobody is a stranger and everyone is always welcome. The people, the culture, the food, the lifestyle, the sweet tea… Everything is a little better with a little Southern in it. Everything.

What are some tips you would give women to stay inspired through lives trials and tribulations? As women, many times we put ourselves last behind work, family, and other life obligations and, eventually, it will take its toll. When I turned 40, I evaluated everything in my life. As a new mom I was spreading myself too thinly and not using my limited resources wisely. I decided to streamline things and only give time to the things that really mattered. While some women dread the big 4-0, I never felt more confident and free. I now give time to the people who value me as much as I value them. I stop to enjoy the little things and, in return, I don’t stress over the big things as much. I think the best advice I can give is to take time to live in the moment. It is so easy to get caught up in the minutiae of life. Do some things just for yourself. Find a passion and make time for it. Visit with friends. Travel when you can – even if it’s just a couple hours out of town. It’s amazing what a change in scenery can do for your overall perspective.

How do we begin to create a better life? I think the best life can be had when you are honest with yourself. Figure out what is really important and focus on those things. There are so many distractions pulling us away from where we should be. Figure out what matters and focus on attaining those goals. I’m a big list maker. I make lists for my lists. It helps me get it out of my head and somewhere safe so I know I won’t forget. I prioritize the things that are most important to me and my family and focus solely on those. People tend to think I have more hours in my day than they do. I assure you, that is not the case. I have become very good at giving my resources to the things that I think are important and letting the rest go. I pride myself on being perfectly imperfect 98% of the time.

How would you describe your personal style? I would describe my style as classic with a twist. I appreciate clean lines, thoughtful design, and quality made things. I am the type of person that would rather have 3 really great pairs of shoes instead of 25. I also like transitional items that can pair with many different things. If a current trend strikes me, I might buy one quality item to spice things up; but the majority of my wardrobe is quality over quantity.

What was your favorite thing to wear as a child? When I was younger my mom really enjoyed dressing me well. I can’t take credit for my style back then, but my teachers said I was the “best dressed kid in elementary school”. My mom sewed in her free time and made many European-style dresses for me with clean lines and chic styling. She was also fortunate to have the stores in NYC to shop from and she always looked for unique quality items, many of which I still have tucked away today. I even have several hand-smocked items. I guess she knew I’d soon become a Southern girl! I have taken the same interest in dressing my son. I love pulling pieces together for him and he has a fantastic sense of style. He’s all about the accessories- scarf, trilby hat, pocket square… it’s a hoot.

What is your favorite thing to wear now? Right now you will most likely find me in a cashmere Joie sweater, DL jeans, and Chanel riding boots. I’ve had these boots for about 10 years and they look even better now than the day I bought them. I love that they work at the barn while I watch my son ride horses, but they can also take me straight to work or lunch with a girlfriend. I have a thing for leather jackets too. My favorite is from Vince. It’s a tri-color chocolate, tobacco, and black slouchy asymmetrical cut. It adds a little “edge” to my casual yet classic ensemble.

What is your favorite quote? I love quotes. I peppered my first book with over 100 of them. But my life has always been about taking opportunities as they present themselves and figuring things out along the way. Confidence is my best accessory…

“Sometimes you just have to take the leap and build your wings on the way down” -Kobi Yamada


Who have played mentor roles in your life? Overall, my parents have had the biggest effect on the person I have become. My father is always a source of wise council and my mother is the one who initially taught me all the skills I now enjoy. My high school science teacher, Darcy Iams, provided the spark and influence for me to pursue a Bachelors degree in Biology. My friend, Bobby Flay, helped me navigate a career change into the entertainment industry.

What advice would you give to women in their 20s?

Career: Believe in yourself. Be patient with success. Take risks. Fail. Get back up and try again. Take opportunities as they present themselves even if you think you are not ready or prepared for them. You might surprise yourself.

Friends: Surround yourself with a small group of friends who value and support you and truly have your back. This is as important now as it will be 20 years from now.

Boys: Don’t look for a husband right after college. This is the one time in life you are free to be and do whatever you want. Don’t be afraid to be alone. That goes for roommates too. At some point, live by yourself for at least a short while.

Money: Stop comparing yourself to everyone else. Do not go into debt buying useless crap while trying to keep up with your friends. Borrow the least amount of money you have to on credit. The poorer you are in your twenties, the richer you will be in your thirties and beyond. Buy what you need, and when you can temporarily go without, save and then buy the best you can. Treat yourself from time to time and remember that experiences and travel are always smarter investments than things.

Travel: Travel whenever you can. See more for less. I recommend quantity of locations over quality of accommodations. You can stay in the fancy hotels in your 30’s when expendable money is more plentiful but time and flexibility are not.

Listen to your Mom: Don’t drink so much. Use sunscreen. Love yourself in that bikini.