There are trips you pack for, and then there are trips you dress your way into.
Louisville turned out to be a little of both.
I had made an outfit plan before we left — of course I had. We were celebrating milestone birthdays, touring distilleries, going out to dinner, walking through downtown Louisville, crossing a pedestrian bridge, cooking for a house full of friends and generally trying to fit a very good time into a handful of days.
I wanted to look pulled together.
I also wanted to be comfortable.
And, perhaps most importantly, I did not want to spend a birthday weekend thinking about my clothes.
What I didn’t realize until afterward was that I had packed in a way that made perfect sense for Kentucky: linen, denim, good leather, comfortable shoes, a little polish, a little practicality and just enough personality to keep it all from feeling like a uniform.
Which, as it turns out, is not so very different from Louisville itself.
Thursday: Dress for the Life You’re Actually Having
Thursday was hot, and it was a travel day.
There were groceries to buy, a rental house to organize and friends arriving later, so this was not the moment for precious clothing.
I wore linen pants, Adidas sneakers, a short square-cut linen “trucker” jacket with chest pockets and one of my favorite graphic T-shirts — a New York Public Library fundraiser shirt printed with old-fashioned library stamps.
It was comfortable, washable and perfectly capable of hauling groceries.
And then my friend and I went to Jack Fry’s.
She looked beautiful in an off-the-shoulder blouse. I looked down at myself and thought, well...here we are.
So I tucked in the T-shirt, buttoned my linen jacket, put my hair into a French twist with an elegant clip and relied on gold Coach hoops, a gold chain and lipstick to do what gold jewelry and lipstick have been doing for women forever.
They pulled the whole thing together.
And here is one of my most practical fashion observations from the entire trip:
Nobody notices what you’re wearing below your waist when you’re sitting at a table.
There we were, eating those wonderful shrimp and grits at Jack Fry’s, surrounded by beautifully dressed Louisville women, and I didn’t feel underdressed. Jack Fry’s has been part of Louisville since the 1930s, and its current menu still includes the shrimp and grits that helped make it a local favorite.
I felt like myself.
Maybe slightly more polished than I had been in the grocery aisle an hour earlier, but still myself.
That turned out to be the theme of the weekend.
Friday: Bourbon Ready
Friday was our first full day downtown: lunch, Kentucky Peerless and Angel’s Envy.
It was hot again.
I wore barrel jeans, a white linen blouse half tucked into a wide leather belt, comfortable olive Mary Janes, sunglasses and one of my favorite travel finds: a circular hatbox-style handbag I bought on Île de la Cité in Paris.
That outfit may have been my favorite of the trip.
It could sit under a chandelier in a beautiful bar without looking out of place, but it could also lean against a scarred wooden counter in a dive bar with beer coasters everywhere.
That is an excellent quality in an outfit.
Several people told me I looked skinny. Several told me I looked good.
I’m not going to pretend I didn’t enjoy hearing it.
But what I remember more clearly is that I felt put together without feeling dressed up.
The linen blouse kept me cool outside and warm enough inside the aggressively air-conditioned buildings. The jeans could take a full day of walking. The shoes did not make me regret my choices by 3 p.m.
And the Paris handbag gave the whole thing a little wink.
Wisconsin woman. French handbag. Kentucky bourbon.
That sounds about right.
Louisville Has Been Dressing Up for a Long Time
The interesting thing is that Louisville has always had this tension between practicality and presentation.
Horse country requires clothes that can function. Bourbon country grew from agriculture, warehouses, barrels and hard work.
But Louisville also became a city where people dressed to be seen.
The first Kentucky Derby was held in 1875, and its founder, Meriwether Lewis Clark Jr., deliberately borrowed from the customs of European racing. Contemporary accounts and the Kentucky Derby Museum describe the races as social occasions where fashionable dress was very much part of the spectacle.
By the early 1900s, Louisville women could shop at substantial local department stores such as Kaufman-Straus, founded in 1879, which sold women’s clothing, furs, linens and menswear from its downtown Fourth Street operation.
Rodes arrived in 1914 as a Louisville menswear shop and remains a family-run local retailer more than a century later, built around tailoring, quality and what it calls “international style and local traditions.”
And Louisville has preserved far more of that clothing history than I realized. The Filson Historical Society holds more than 5,000 garments dating back to the early 1800s, encompassing everything from ball gowns and weddings to sportswear, bathing clothes and blue jeans.
In other words, Kentucky fashion history is not just Derby hats.
It is work clothes and society clothes.
Practical clothes and beautiful clothes.
Clothes for living.
I like that much better.
Saturday: Green, Denim and the Bourbon Trail
Saturday was our full bourbon-tour day: Bulleit, Castle & Key and Woodford Reserve.
I wore my barrel jeans again — travel wardrobes are allowed to repeat themselves — with a sleeveless evergreen ruffle-neck blouse, a black linen jacket and leather sandals.
The jacket could come off when the heat became ridiculous and go right back on when the air conditioning became equally ridiculous.
The green was intentional.
Green makes my eyes look very blue-green, and apparently everyone else noticed too because I received compliments on it all day.
More importantly, when I look at the photographs from Saturday, I like the woman I see in them.
That is not something I have always been able to say.
And somewhere between the barrels and rickhouses and limestone and old stone buildings, another piece of Louisville style started making sense.
Bourbon SWAG Has Grown Up
Distillery gift shops have become surprisingly good at translating bourbon culture into clothes.
There are still T-shirts, of course — as there should be.
But the better shops now sit somewhere between heritage workwear, country-club casual, equestrian dressing and regional souvenir.
Bulleit’s current merchandise includes trucker and twill hats, barrel-stave hats, sweatshirts, tees and bandanas — casual, graphic, workwear-adjacent pieces that make sense for the brand.
Peerless sells classic tees, trucker hats, beanies and other logo clothing; our two birthday girls even came home with Peerless T-shirts.
At Castle & Key and Woodford Reserve, what caught my attention was how easily the merchandise crossed over into broader Kentucky lifestyle dressing: totes, sweaters, jackets, shirts and accessories that looked equally at home at a distillery, a country club or somewhere near a horse paddock.
That blend makes sense.
Kentucky style has been shaped by horses and bourbon for generations, and modern visitors are essentially buying wearable pieces of that story.
I bought a Bulleit hat for my husband.
I may borrow it.
I also bought a wooden notebook from a “buy one, plant one” display. A tree is planted with each purchase from that collection, which struck me as a much nicer souvenir than another object destined for a drawer.
And yes, bourbon chocolates came home too.
Fashion has its limits.
A Kentucky Woman Who Took Style Very Seriously
If Louisville needs a fashion patron saint, Mona Bismarck makes a compelling candidate.
Born in Louisville in 1897, Mona Bismarck became an international style figure and was the first American named the “Best-Dressed Woman in the World” by a panel of Paris couturiers in 1933. The panel included names such as Chanel, Lanvin and Vionnet, and Bismarck later became closely associated with Balenciaga.
The Frazier History Museum mounted a retrospective of her wardrobe in 2018 featuring dozens of ensembles spanning the 1930s through the 1970s.
This is the point where fashion history can become intimidating very quickly.
So let me say this:
I am not suggesting that anyone needs Balenciaga to tour a rickhouse.
What I like about Mona’s story is the reminder that Kentucky and couture were never mutually exclusive.
Neither are denim and lipstick.
Neither are sneakers and gold hoops.
Neither are practical clothes and beautiful ones.
Sunday Morning: Absolutely Not Couture
Sunday morning involved athletic clothes.
We walked the bridge.
We cooked.
We chopped and stirred and set tables and got the house ready for a birthday party.
There are no profound style lessons here.
Sometimes the correct outfit is simply the one you can sweat in.
Sunday Night: The Green Dress
That evening I changed into my green Donna Karan dress.
It is difficult to describe because it has an almost old-fashioned quality to it — feminine, a little nostalgic, and avocado green, which made it perfect for our 1970s-inspired birthday celebration.
It also has pockets.
Any dress with pockets immediately rises several places in my rankings.
I wore my comfortable olive Mary Janes, put my hair into a French knot and fastened it with my golden Bakelite-looking hair clip.
And I left the cowboy hat off.
The hat was fun.
The hat was Kentucky.
The hat was not me.
That distinction has become increasingly important to me.
Travel should allow a place to influence you. It should not require you to become a caricature of the place.
You can go to Paris without wearing a beret.
You can go to Kentucky without wearing a cowboy hat.
You can admire both.
I received wonderful compliments on the dress all night.
And yet it was the one outfit in which I felt slightly uncomfortable.
Not because there was anything wrong with the dress.
I just do not wear dresses very often anymore.
I used to.
Somewhere along the line that changed.
Age, life, habit — probably some combination of all three.
But I love the dress enough that I want to figure out how to wear it again. I can already see it for work with a cropped camel cardigan, a fitted chocolate-brown jacket, or a soft cream knit worn open so the shape of the dress still shows.
Because perhaps part of finding your style again is not automatically discarding the things that feel unfamiliar.
Sometimes you need to reacquaint yourself.
Find your own everyday style
If this trip’s wardrobe has inspired a look of your own, explore my Everyday Style collection for relaxed clothing and accessories. These are selected finds, rather than an exact shopping list of the outfits pictured here.
As an Amazon Associate I earn from qualifying purchases.
What I Would Pack Again
If I went back to Louisville tomorrow, I would not reinvent the suitcase.
I would take the white linen shirt.
The barrel jeans.
The linen jacket.
The green blouse.
Comfortable shoes.
Gold jewelry.
Lipstick.
A good handbag.
And something that makes me feel a little bit special for dinner.
The practical lesson is simple: Bourbon Trail dressing benefits enormously from layers, breathable fabrics and shoes you can genuinely walk in.
The less practical lesson is better:
Pack things that still feel like you.
The Woman in the Mirror
Before I started writing this blog — before I started slowing down enough to really look at my life and at the things I enjoy — I was much harder on the woman in the mirror.
I saw what I wanted to change.
I saw age.
I saw imperfections.
I saw all the ways I thought I ought to be different.
But somewhere in the process of paying attention — to cooking, style, travel, history, entertaining, gardening, art, friendship and all the things that make a life feel rich — that began to change.
And when I look at the woman in the mirror in Kentucky?
I love her.
This is me.
A little Wisconsin, a little French, a little Kentucky when I am in Kentucky, Palm Beach when I am in Palm Beach and California when I am in California.
None of those women is a costume.
They are all me.
Maybe that is one of the gifts of getting older.
I’m less interested in dressing like the woman I think I’m supposed to be and far more interested in dressing the woman I actually am.
She likes linen and old houses, lipstick and comfortable shoes, bourbon history and good wine, gardens and art and long dinners with crazy friends.
She carries a Paris handbag into a Kentucky distillery.
She wears sneakers when there are groceries to haul.
She sometimes feels awkward in a dress and wears it anyway.
She cooks.
She learns.
She asks questions.
She tells the truth about what she likes and what she doesn’t.
She is not a young influencer.
She has lived long enough to know a few things.
She is imperfect and still works very hard at being a good wife, friend, daughter, sister, and human being.
I know her now.
And I rather like her.
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