Hollywould founder/creative director Holly Dunlap made a name for herself designing flirty, feminine shoes, cute enough to kick around in at the Palm Beach B&T, and sturdy enough to dance atop Bungalow 8’s banquettes ‘til the wee hours. As she once told Newsweek, her shoes are “not for the ladies who lunch, but the girls who sleep through lunch because they’ve been partying all night.” The prim-party-girl aesthetic has won her a legion of devoted customers including Chloe Sevigny, Liv Tyler, Sophie Dahl, and Gisele. But no one pulls off the look like Dunlap, who’s always impossibly chic, even after a long night of palazzo party-hopping in Florence, Italy, where she lives and works for half the year. 

Here, she divulges her favorite places to drink, dance, and buy vintage Missoni in Florence—a city that overflows with fine art and flavorful chianti, but, as Dunlap claims, is devoid of anything resembling a cutting-edge underground scene: “Florentines feel like they contributed enough culturally during the Renaissance to last a few centuries, and as a result have been resting on their laurels listening to bad house music ever since.”

In her own words: 

Food & Drink:

For Breakfast - Café Giacosa (also known as the Cavalli Café) makes the best cappuccino in Florence. Best spot to people-watch, as everyone is in Cavalli and the men are three times the age of their girlfriends. Best plastic surgery in town too.

For Weekend Brunch - Hotel JK (also good for cocktails) on Piazza Santa Maria Novella. They serve a real American brunch to the hip Florentine  crowd.  Great when you’re hungover from hanging out on their rooftop terrace the night before.

For Lunch - Osteria Santo Spirito. They have great carpaccio and yummy olive paste to eat with your bread.  And they give you crayons with your menu.

For Wine/Snack - Verrazzano for cheese, wine, and focaccia. It’s a great place to get drunk and sit for hours. Best wine selection in town served with a million choices of cheese and yummy focaccia combos, like pear & pecorino.

For Tea - The Hotel Lungarno lobby. If Agatha Christie set a novel in Florence today, everyone would have tea at the Hotel Lungarno. Old-world chic, with an average age of about 70. 

For Pre-Dinner Cocktails - Roof of the Hotel Continentale is a great spot to sit and drink and drink. You’ll see everyone from the Puccis to the Ferragamos.

For Dinner - Quattro Leoni on Piazza Quattro Leoni. The fiocchetti pasta is amazing!  Or, Il Parione on Via Parione. Must have their cheesecake for dessert. Both places are great and both waitstaff is scandalous. Stay late enough and you may end up there all night.  Pruto in Piazza Tasso serves the best fish in town to in-the-know Florentines.

For Post-Dinner drinks - Harry’s Bar -- bellini mandatory.  Despite its American name, anyone who is anyone Florentine eats here. It’s generally the men-with-mistress crowd, where wives are an endangered species.

For Early Disco - just above the Louis Vuitton store in Piazza Strozzi, the disco Colle Bereto’s upstairs lounge, which is called “Prive Attico,” serves strong drinks and good music.

For Late-Night Disco - Full Up is definitely a hot spot until 4am, but be  prepared for an average age of 24 or less.

Shopping: 

Elio Ferraro has the best vintage in Florence. Overpriced, but where else will you find this much Missoni and Pucci in one place?

Flair home store is a great spot for “Italian Modern”-style furniture with classical touches.  Unfortunately, it’s been lately discovered by every American interior mag, so you’ll probably see “Flair for Target” soon.

Gerard is good for edgier stuff like Balenciaga. It’s kind of a mixture of Colette and Supreme, keeping in mind this is Florence, so it’s not as cool as it sounds.  A Gerard T-shirt is a must-have for anyone who wants to prove they know the DJ (or at least a DJ).

Luisa Via Roma is Florence’s version of Jeffrey, but with fewer shoes and more leopard prints. Recently added Juicy Couture, much to their discredit, but it’s still the coolest multi-designer shop in Florence.

Farmacia Santa Maria Novella is an amazing monastery-turned-pharmacy where you can get any herbal remedy, as well as soaps made by monks.  If you go in the back room, you also have a great view of the courtyard where the Florence police exercise – hot hot hot.

The Mall contains outlets including Pucci, Valentino, Gucci, Tod’s, McQueen, Loro Piana, etc, etc, etc.  It’s about 30 minutes south of Florence off A1 autostrada, headed to Rome. Exit is “Incisa,” and there are signs from there.

Spa: 

Gabrio Staff Olimpo gives a manicure that lasts 3 weeks and serves a “relax lunch” for 20 euro, which includes a healthy lunch prepared by the Hotel Bristol’s four-star chef along with a massage or Turkish bath.   

Getaways:

Forte dei Marmi is like the Hamptons, but with even more flash. You see more jewels on that beach than you see on an Oscars red carpet, and everyone who is anyone has at least 2 Lamborghinis.

Lucca is the best non-touristy town in Tuscany and has great free summer concerts where you can see big names like Buena Vista Social Club in a piazza under the stars with 200 people while having pre-dinner cocktails. 

San Gimignano is a beautiful feudal city with Gallery Continua, one of the best contemporary-art galleries in Europe. It’s such a strange location for modern art that it’s worth a visit!

Go There:

Café Giacosa, Via Tournboni 83r, 011-39-055-239-6226

Hotel JK, Piazza Santa Maria Novella, 7, 011-39-055-264-5181

Osterio Santo Spirito, Piazza Santo Spirito 16r, 011-39-055-238-2383

Cantinetta dei Verrazzano, Via dei Tavolini 18-20r

Hotel Lungarno, Borgo San Jacopo, 14, 011-39-055-272-61

Hotel Continentale, Vicolo Dell'Oro, 6r, 011-39-055-272-62

Quattro Leoni, Via dei Vellutini, 1r, 4leoni.com

Il Parione Cartoleria, 10 Via dello Parione

Pruto, Piazza Torquato Tasso 9R

Harry’s Bar, Lungarno A. Vespucci 22r, 011-39-055-239-6700

Full Up, Via della Vigna Vecchia 25r, 011-39-055-293-006

Elio Ferraro, 47R Via del Parione, 011-39-055-290425

Flair, Piazza degli Scarlatti 2R, Lungarno Guicciardini, 011-39-055-28-0338

Gerard, 34/36 Via dè Pecori, 011-39-055-282491

Luisa Via Roma, 24 Via Roma, 011-39-055-217826, luisaviaroma.com

Farmacia Maria Santa Novella, 6 Via della Scala, 011-39-055-216276

Gabrio Staff Olimpo, 5 Via de’ Tomabuoni, gabriostaff.it

Hollywould, 198 Elizabeth Street, NYC, (877)456.8349; ilovehollywould.com

Holly Dunlap photo courtesy of Patrick McMullan, patrickmcmullan.com