Exclusive events where empowered women come together to explore and express themselves freely
Stiletto Social is not an event brand. It is The Group itself, in a ladies only format. On any given evening, the room holds long-standing members of The Group alongside a small number of carefully introduced newcomers, all of them women, all of them vetted for the only things we screen for: character, warmth, and discretion.
There is no question of orientation. No question of relationship status. No question of experience. Married, single, partnered, curious, certain, or simply social: the invitation asks only one thing, that the evening be better with you in it. Like every Group gathering, the guest list is truly selective, and that is precisely why the room feels the way it does.
Half the room already belongs. The other half was chosen.
Which makes you, on your first evening, in excellent hands.
We will spend the night at the dock aboard a private yacht, so privacy is assured. The crew will be released for the evening, so it will just be us ladies on board.
Beginning at 9 PM, let's enjoy some music, carefully blended cocktails, and each other's company till the wee hours, without prying eyes and without pressure of any kind.
Request an InvitationA member of The Group personally vouches for a woman she already knows. The oldest way in, and still the fastest. The best connections come from within.
For women without a connection inside The Group, a short application begins a conversation, and if it's a fit, an invitation follows. One evening, hosted well, is how the relationship begins.
Each is hosted by Ann, limited by the room, and held to the same discretion as every Group gathering. We would rather host one evening you remember for a decade than fifty you cannot tell apart.
Between Signature evenings, the ladies of Stiletto Social gather in cities around the country for a ladies only edition of The Table: a multi-course evening at one of the city's finest restaurants, with the same curated company and no agenda beyond the conversation.
Dinner is the easiest first step there is. Everyone already knows how dinner works. Come meet a few of us where the only thing on the menu is the menu.
Sometimes it's a party. Sometimes it's just dinner.
It is always The Group.
A hostess greets you at the door, champagne in hand, and makes your first introductions. Most women arrive alone. None stay that way for long.
Gourmet bites, artisan cocktails, and the easy conversation of a room where everyone was chosen for their company.
A performance, perhaps a DJ, a little dancing, something to talk about. The evening warms on its own schedule.
From there, the evening becomes whatever the room wishes it to be. Privacy is assured, and the staff retire early.
I came knowing no one and nervous as anything. By the second glass of champagne I understood: this isn't a party you attend, it's a room you join. I've been part of it ever since.
Curated. Exclusive. Unforgettable.
Extraordinary destinations. Epic co-ed weekends.
The Group's celebrated dinner series, coast to coast.
Our private retreat. Relax. Recharge. Reconnect.
Your Group, in your pocket. Connect anytime, anywhere.
Ladies,
I attended my first Group event in 2015, newly divorced, as the guest of a couple who insisted I simply come and see. I remember the nerves on the drive over, and I remember how quickly they vanished once I was inside. A year later, I was hosting the evenings that had welcomed me. The secret has not changed: invite wonderful women, look after them properly, and let the night take care of itself.
If you are reading this as a member, you already know I will be at the door. If you are reading this as a newcomer, know that I read every introduction myself, and that the nervousness you may feel is the most common thing in the room. It never survives the first glass of champagne.
Come for the company. Everything else is entirely up to you.
Kisses, Ann
Stiletto Social is by invitation, and every evening is limited by the room. If a member referred you, mention her name. If not, tell us a little about yourself and Ann will take it from there. Applications are read personally, held in strict confidence, and never shared. Discretion, after all, is the house style.
Request an Invitation