Turning 40 was either an excuse to hole up at home nursing my new set of eye wrinkles, or an opportunity to share something fabulous in Italy with the friends I have scattered across California, New York and Europe.  After the sting of being slapped with four full decades had cooled, I decided to celebrate. I began to plot my party with as much exactitude as my wedding in Portofino seven years prior.

From a planning standpoint, both events presented the same challenge: how to dangle a big-and-juicy-enough carrot in front of my American friends to convince them to voyage up to 5,000 miles to Italy for a mere three days?

The answer involved concocting an ambitious affair that would be tantalizing as a mini-vacation and convenient enough to work around the schedules of the travelling guests. My birthday party took place over three days in Rome in May, a dead month in the fashion world but a glorious time for Titian blue skies and Apollo-strength sun.

Why Rome? Well, no one considers Milan (where I live) a vacation destination. Milan is a slick, somewhat-well-functioning city for business. When it comes to playing, partying, eating, shopping and eye goggling, Rome is Italy’s clear-cut champion. On a logistical level, however, it’s a disaster. Everyone is so busy staying up all night at al fresco parties on someone’s 15th-century terrace that working the next morning becomes extra-curricular. La dolce vita, it turns out, is a sickly sweet web that traps its locals in a state of inertia, which means ‘planning’ anything is next to impossible.

Still, I was determined. I hired an affordable event planner who possessed all the good qualities we love about Romans (friendly, well-connected, bubbly, willing to negotiate any price down, game for eating anytime) as well as a few of the bad ones (leisurely and disorganized—which are not flaws, by the way, in any Roman rulebook). Then I did as the Italians do, and called every friend I knew for advice, help and moral support.

For the invitations, a graphic designer friend scanned my favorite vintage YSL 1980s skirt-suit for the cover and letter-pressed the hard cards in gold print at Nava, the printer who does many of Milan’s fashion show invitations.  On one of my two-hour adventures standing in line at the grand Cordusio post office, I serendipitously discovered their ‘vintage’ stamp collection (hidden in dusty boxes) while chatting casually with a bored teller. From this fantastic stash I chose a Medieval-looking stamp the size of a baseball card for my European guests.

A friend also came to the rescue on the most important piece of the party puzzle: The Main Outfit. After lamenting about the lack of options over coffee one day at Caffè Cucchi, my dear friend Francesco Risso, a fashion designer at Prada, offered his services. We decided on a “Scarlett O’Hara meets Paco Rabanne” theme, and he got busy pinning mirrored discs onto his mannequin at home for my top and crafting an enormous lace jacquard ball skirt showered in ostrich feathers that was short in front to show off my Brian Atwood shoes and red-carpet long in the back. Entirely hand-made and fit to my body like a couture creation, the two-piece dress was undeniably original and magnificently over-the-top.

A dress like this called for a location befitting its drama—which we found, after three other location meltdowns, at the 17th-century Villa Aurelia. Sitting atop Rome’s Gianicolo, the romantic, eerily quiet hills adjacent to Trastevere, the villa is ensconced in a peaceful, green park with a dramatic entryway and outdoor garden. We would do the aperitivo outside in the lemon-tree maze, while the dinner would be held upstairs in two adjoining salons with arched frescoed ceilings. Dancing would occur on the ground floor.

I was fussy about the tables, persnickety about every detail. The wine glasses looked 18th century (they were not, of course) with gold trim, and the plates were white with gold trim. I insisted on gold flatware, an expensive detail I’d seen in a Milan residence that I’m thrilled to have splurged on. The caterer’s flower proposals made the tables look like a Radisson hotel, so I hired a creative from Milan’s Tearose flower shop and charged him with making it ‘cheap and cheerful.’ He came up with a blanket of white and green blooms placed in a hodge-podge of small and large sized vases that looked as elegant and homey as a 19th-century vanity table.

I’ve always loved the look of a super long, single imperial table rather than a cluster of circular tables. But we had two rooms, so my husband and I split up and each hosted one long table of 60 guests. The dinner was seated but quick: two pasta dishes (an Italian tradition), then branzino with vegetables, after which Francesco helped me slide from my 20-pound ball skirt into a dancing-friendly vintage black skirt and Gianvito Rossi sandals. We did the cake downstairs in the middle of the dance floor, where my brother reminded the guests that I’ve been dressing like a fashion maniac since I was five and my husband coined the phrase #jjstyle for my too-much exuberance which, thankfully, he adores. Fifty of the guests finished the night at 2am tumbling into Jackie O’s, a leather-lined nightclub frozen in the 1970s along Via Veneto, where we all got crushed on the dance floor by overly tanned, cigarette-smoking locals.

That was just the main event. Our three-and-a-half-day weekend was peppered with casual cocktails, family dinners, leisurely breakfasts, tours of Roman palazzos, a gay wedding officiation for friends, and a vintage Vespa ride for 75 guests that cruised the city and included a pit stop on the Gianicolo hills, where we enjoyed coffees and an epic view of the eternal city. Joining me were friends I’ve known since I was six, girls I went to college with, sorority sisters, New York fashion editors, fellow writers, old and new Milan friends, London locals, and fashion designers I love and admire. So what did I do next? I jumped for joy, kicking my heels into that Titian blue sky like a 14-year-old cheerleader in a 40-year-old’s body.

– J.J. Martin