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A Behind-the-Scenes Look at Esquire’s Party for the 20th Anniversary of the Big Black Book

At the Ludlow House on the Lower East Side, a bunch of New York’s coolest people gathered to raise a glass to the essential guide to style and luxury.

By Swedan Margen

A Behind-the-Scenes Look at Esquire’s Party for the 20th Anniversary of the Big Black Book
Several copies of Esquire magazine displaying an article about Glen Powell on a metal table.

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The October/November 2026 issue of Esquire, which includes the latest Big Black Book.

Two men enjoying drinks at a bar, one wearing sunglasses and a denim jacket, the other in a black jacket, both smiling.

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Josh Peskowitz and Eugene Tong.

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Four individuals dressed in stylish attire pose together in a modern indoor setting, holding a magazine.

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Alfonso Fernández Navas, Zach Weiss, Nick Roberts, and Jake Woolf.

A joyful woman laughing and engaging with friends in a lively social setting.

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Meredith Bligh.

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Two people posing together at a social gathering, surrounded by others in a lively atmosphere.

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Willa Bennett and Alfonso Fernández Navas.

Two men laughing and engaged in conversation, set against a dark textured wall.

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Hasan Minaj and Esquire editor-in-chief Michael Sebastian.

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Two people sharing a joyful hug while a woman smiles and holds a drink in a cozy social setting.

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Eugene Tong and Mimi Fukuyoshi.

Four people posing together at a social gathering with drinks in hand and a casual setting.

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Nick Sullivan, Charlie Sullivan, Florence Sullivan, and Wendell Brown.

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Two people hold drinks while standing in a social gathering, with a dark background and other guests in the vicinity.

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Nick Sullivan and Marisa Lee.

People mingling at a crowded social event, with various attendees engaged in conversation and drinks.

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Jake Mueser and Nick Roberts.

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A lively gathering with people chatting and enjoying themselves in a social setting.

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Hasan Minaj, James Scully, and Jake Woolf.

A man in a navy blazer speaks into a microphone while another man smiles with a drink in hand, against a reflective backdrop.

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Michael Sebastian and Nick Sullivan.

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Five people posing together in a casual indoor setting, smiling and dressed in stylish clothing.

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Nick Sullivan, Michael Stefanov, Wendell Bown, Nic Screws, and Sam Spector.

Four friends enjoying a night out, smiling and posing together in a stylish bar setting.

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Andrea Rios, Emma Saxon, Leigh Cohen, and Michael Carnavale.

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Group of five people enjoying drinks at a social gathering in a stylish interior setting.

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Kavi Moltz, David Seth Motlz, Emily Goldsher-Diamond, Jason Diamond, and Michael Sebastian.

Two men speaking at an event, one reading from a paper while the other holds a microphone and addresses the audience.

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Nick Sullivan and Michael Sebastian.

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Four people at a social gathering enjoying drinks and engaging in conversation.

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Lucy Kaylin, Julia Fry, John Wattiker, and Willa Bennett.

Two men engaged in conversation at a social gathering, one holding a drink and wearing a black sweater and beanie.

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Jake Woolf and Hasan Minaj.

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Three well-dressed men posing together at a social event, with drinks in hand and a festive atmosphere.

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Michael Sebastian, Rōze Traore, and Malique Morris.

Group of people conversing at a social gathering, with one man smiling and wearing a suit in the foreground.

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Alex Badia.

Originally published by esquire.com. Syndicated material does not necessarily reflect the views of Vanity Fair Fashion.

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A Behind-the-Scenes Look at Esquire’s Party for the 20th Anniversary of the Big Black Book - Vanity Fair Fashion