Some Nashville evenings begin with music. Ours began with a hat.
Before dinner, we made our way to Planet Cowboy on 12th Avenue South, a wonderfully theatrical shop devoted to the art of Western style. It is part boutique, part workshop and part Nashville souvenir that you can actually wear. The shelves were filled with cowboy boots, hats and accessories, but the real attraction was the Hat Bar, where a plain hat can become something entirely personal.
I already had a hat. What I wanted was a little more Nashville in it.
The proper term for what followed is hat customisation, although “customisation” feels too ordinary for the experience. Planet Cowboy helped me update the hatband and add feathers, or feather adornments, to give it a more distinctive Western character. A hatband is the decorative band fitted around the base of the crown, while the feathers are tucked into it as a flourish. Together, they transformed the hat from something I owned into something that felt connected to the city.
There was a genuine pleasure in making those choices. The staff understood that a cowboy hat is not simply an item of clothing. It is a statement, a keepsake and, in Nashville, an invitation to participate in the city’s particular romance with country music and Western style. They were knowledgeable without being intimidating, enthusiastic without being pushy and generous with their ideas.
Planet Cowboy is the kind of place where you can arrive looking for a hat and leave with a story. Its custom Hat Bar allows visitors to shape, decorate or personalise their own piece, with options including leather bands, feathers, pins, initials, dates and hand-drawn designs. The experience feels creative rather than commercial, and the result is far more meaningful than anything picked up from a standard souvenir shop.
By the time we left, my hat had a new personality. It was ready for dinner.
Alla Vita, at 523 Houston Street in Wedgewood-Houston, was busy in the way a restaurant becomes busy when people are there because they genuinely want to be. The neighbourhood, just south of downtown, has become one of Nashville’s most interesting areas for food, art and independent creative businesses. Alla Vita fits comfortably into that setting, bringing a polished but welcoming Italian sensibility to a city more commonly associated with hot chicken, barbecue and biscuits.
The restaurant was trendy, warm and full of movement. There was a glow from the bar, a lively hum from the dining room and the unmistakable sense that the evening had begun before we arrived and would continue long after we left. The design was stylish without becoming precious. It had the kind of atmosphere that encourages a second cocktail, another plate and the belief that dinner should take as long as it takes.
Alla Vita means “to life,” and the name is well chosen. The menu is designed around sharing, conversation and the uncomplicated pleasure of eating something delicious with people you like.
We began with a salad of tomatoes, burrata, cherries, mint and pistachio. It was bright and generous, with the sweetness of the tomatoes and cherries balanced by the creamy burrata and the freshness of the herbs. It looked beautiful without being overly arranged, as though the ingredients had simply been gathered at their best and allowed to speak for themselves.
The menu moves easily between familiar Italian comfort and more considered combinations. There are wood-fired meatballs with roasted tomato sauce and Parmesan, arancini with scamorza and ’nduja aioli, roasted Spanish octopus with eggplant and salmoriglio, and a whipped ricotta seasoned with chili, honey and oregano. Even the dishes that sound simple carry a certain richness and confidence.
The handmade pasta is where the restaurant becomes difficult to resist. The rigatoni alla vodka arrives with Calabrian chili, giving the familiar sauce a deeper, warmer edge. The cacio e pepe ricotta dumplings are a softer, more luxurious interpretation of the classic Roman combination of cheese and black pepper. There is tagliatelle with beef shank ragù, cappelletti with chanterelle mushrooms and sweet corn, and squid ink bucatini with prawns, mussels, calamari, roasted tomato and chili.
Then there is the pizza, thin and wood-fired, with toppings that move well beyond the ordinary. San Daniele prosciutto is paired with black pepper, smoked pecorino and arugula. A mushroom pizza comes with black truffle, caramelised onion and taleggio. The fennel sausage pizza brings pickled chilies, roasted garlic and fontina into the conversation.
But the cocktails were the moment I knew Alla Vita understood the assignment.
“Oh my God” is not usually considered a technical tasting note, but it was the most accurate response. The drink in front of me was tall, pale and cold, crowned with fresh mint and carrying the kind of citrus brightness that makes you immediately want another sip. Alla Vita’s drinks lean into vermouth, amaro and seasonal spritzes, which makes them particularly well suited to the food. They are not heavy or showy. They are balanced, refreshing and quietly clever.
There is a lightness to the drinking experience, even when the food is indulgent. A cocktail cuts through creamy pasta. A spritz wakes up a rich pizza. A well-made amaro drink makes you feel sophisticated enough to order dessert.
Alla Vita is part of the Boka Restaurant Group and was created by chef Lee Wolen, whose Chicago restaurant Boka has earned Michelin recognition. The Nashville restaurant carries that background with confidence, but it does not feel like a visiting concept trying to impose itself on the city. It feels at home in Wedgewood-Houston.
That was the pleasure of the evening: a newly decorated cowboy hat, a busy Italian restaurant, excellent service, handmade pasta, wood-fired pizza and cocktails that made the table pause.
Nashville is often sold through its music. But some of its best experiences happen between the songs, when you are choosing a feather for your hat, sharing a plate of burrata and realising that the night has become much better than you expected.
Explore Planet Cowboy’s Hat Bar and view Alla Vita’s current menu.
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