In the year 2000, I met my husband. He was driving a red Ford pickup truck in New York City and clocked in at 6’3”; bonus, he was Jewish. After years of sex IN the city, this handsome, charming man was just my size. And this tall drink of bourbon was also from Louisville, KY, so a bit of an exotic creature for this Manhattan girl.
I had never met anyone from Louisville (pronounced Loo-uh-vul) before. Still, I was always fascinated with the South (though Kentucky is technically Southeast but Southern enough for this Yankee). My uncle lived in New Orleans for most of his adult life, and that city has always held me in its Sazerac, jazz-infused, beignet-powdered gaze. So when I first went home to meet David’s family, I was immediately smitten with leafy Louisville. On a good day, you can get there in just under two hours from Manhattan, and its proximity to cool cities like Cincinnati and Nashville gives it bonus points for those of us who like to do weekend trips.
Louisville has an indie spirit, warm people, and loads of Southern charm
Birthplace of Muhammad Ali, Hunter Thompson, and Jennifer Lawrence (the musician Jack Harlow is a newer famous son), Louisville has an indie spirit, warm people, and loads of Southern charm. College basketball is legendary, as is the annual Kentucky Derby (the inspo for this hat). Nearby Lexington has some of the most beautiful horse country I have ever seen, with rolling hills and natural beauty in spades. My father-in-law hosts the annual St. James Court Art Show, the most significant art show in the country in old Louisville, in a charming mixed neighborhood full of beautiful old homes that would cost millions in Brooklyn.
As you also may know, Kentucky is home to bourbon and lots of it. The bourbon trail is a fascinating foray into all things brown liquor, and distilleries like Woodford Reserve roll out the barrels and welcome you to a fun and educational experience. Fun fact: I worked on the launch of Angel’s Envy, an indie brand located in downtown Louisville which recently sold to Bacardi. Admittedly, I prefer scotch, but a mint julep never hurt anyone. Two is another story.
Louisville itself is also highly diverse, politically liberal, and gay-friendly. There is a wonderful sense of community, as evidenced by a fab soiree I attended last week where our hostess wore feathers to welcome a flock of creative types and gay men. She also hosts a salon and acts as a de facto Peggy Guggenheim meets Gertrude Stein of Louisville. I wouldn’t mind being her when I grow up.
The “Lou” also has lots of excellent food. The legendary Pat’s Steakhouse is an old-school icon serving manhattans in leaded cocktail glasses, frog legs, and a sublime New York strip. I also love the martinis at Jack Fry’s, and Lilly’s Bistro has delicious frites and a cute neighborhood vibe. The micro-chain Green District has fabulous salads to go at a reasonable price. There are also lovely coffee shops to soak in some caffeine and all the local flavor.
I love the kick-back kindness of the city
In the new-school sense, the town is up and coming. It’s not as chic as the coasts, but new boutique hotels like the Genevieve in the NULU neighborhood are absolutely a vibe. And in the Highlands neighborhood (one of my favorites for its leafy, laid-back vibe), Frankfort Avenue hosts some fabulous shopping in the form of Peacock for higher-end designer goods like clogs from Beatrice Valenzuela and a wonderful new children’s clothing store called Kiddo owned by a former New Yorker in the fashion business. I spotted her right away in her Max Fish hat because IYKYK. There is also phenomenal vintage shopping on Bardstown Road. I even scored the perfect suede fringe jacket at Leatherhead, a longtime establishment specializing in leather boots, belts, and jackets.
I love the kick-back kindness of the city, and its residents are welcoming in the best of ways. My favorite thing about this town is that, unlike New York, the lead question is never “What do you do?” but more about how you are and what you’ve been up to recently. There is also a lack of pretension I find refreshing. There are not too many fancy cars or designer logos, and there is a quieter approach to money that I admire and appreciate. This lack of superficiality may be my favorite thing about this city, besides the sleepy, old-school, oak-paneled vibe juxtaposed with the shiny, new, and up-and-coming. Oh, and the slower pace may not be my tempo, but perhaps a new frequency would be good for me and my blood pressure.
Another plus is affordability. According to Realtor.com, in April 2023, the median listing home price in Louisville, KY, was $235K, trending up 4.4% year-over-year. The median listing home price per square foot was $149, and the median home sold price was $275K.
With groceries, health care, and utilities anywhere between 3%-14% less than the rest of the country, Louisville is an affordable choice.
I feel like I could finally open up a fabulous little boutique like I’ve always wanted to, albeit tweaked a bit from my NYC point-of-view. I can see it when I close my eyes.
On the cons side, let’s not avoid the racehorse in the room.
Kentucky politics and Mitchy and the boys are a challenge for me. Full stop. Louisville may be a liberal oasis in a right-wing desert, but still. That would take some getting used to and, on a recent trip, the political commercials were frightening. And though diverse, Southern history is haunting and continues to cast a shadow in events as recent as the death of Breonna Taylor.
From a geographic standpoint, the landlock is not lovely. I am a water sign from the coast, and I need an ocean to be happy (or so I think), and the Ohio River is not an ocean. There are also extreme weather issues like tornados and scorching hot and humid summers. Crime is not insignificant, including recent mass shooting events.
On a different note, the shopping in town ain’t all that. The only decent department store is Von Maur, which is more fun to say than to shop. But as my new friends told me from their shop, I could bring the vibe and the inspiration. So perhaps the lack of retail therapy for a gal like me provides an opportunity? This is not a style town, and that’s fine but worth knowing. Sure, the town dresses to the nines for Derby weekend, but I suspect that’s due to a lot of out-of-town influence.
So, could I get lucky in Kentucky?
Hunter Thompson once said, “The world is still a weird place, despite my efforts to make clear and perfect sense of it.” I generally find this true of life, and I’m here for it. So if I told any of my pals I was moving there, they wouldn’t believe me. Because living there would surely seem off-brief for me but, lately, I like that assignment. New York is expensive and exhausting, and the endless need to hustle is getting old. I also love spending time with my in–laws, so being closer would be a lot of fun.
But challenging convention and kinfolk aside, could I be long-term happy in a city that feels more like a small town? And would my New York vibe jibe in the Southland? Would bemusement turn quickly to boredom?
I’m not sure, so the Lou edition of this column is a draw, darlings. So stay tuned to see if old Kentucky could ever be my home.
Talk to me in the comments, y’all. XO