At home with Maxwell Osborne in his New Rochelle family home, Hypebeast and The Macallan meet up with the designer to explore how he celebrates the holiday season and the special moments that bring everyone together. With the holidays quickly approaching, the prestigious whisky purveyor is gearing up for a series of activations that toast to celebration and community, with the first stop highlighting cherished moments at home.

Maxwell Osborne was a designer well before he co-founded Public School alongside Dao-Yi Chow in 2008, and his fashion imprint anOnlyChild, in 2020. Well before he explored the intersections of streetwear and luxury, he knew that the form and function of an object or garment could serve as something much more. These sensibilities shine through in both labels, which imbue sport-inspired, tailored silhouettes with the energy native to New York City — its hustle, passion, and endurance, as well as its vibrant cultural tapestry. anOnlyChild‘s design philosophy builds upon these themes, with sustainable collections designed from deadstock materials, nods to the designer’s Jamaican heritage and a creative ethos that champions the power of identity and philanthropy.

Moving around Manhattan and Brooklyn respectively, Osborne recalls his love of the quintessential loft layout, friends’ spaces punctuated by natural light, high ceilings and furniture setups that prioritize communal exchange. Growing up, he lived in a one-bedroom rental with his mom, which she transformed with an L-shaped wall that uniquely divided the space, a design hack that Osborne has incorporated into his personal work and living spaces. “Something as simple as a curtain can visually separate the space. Lighting, as well, just creates the right energy that makes something feel bigger or grander than it is. A nice rug that always grounds an apartment for sound and warmth. I’m really big on flowers and plants, things that make the space feel warm.”

Around Christmas time, Osborne fondly remembers waiting up with his mom late at night. “My mother would usually have to work around the holidays, so I was used to our celebration happening a day or two before. The one thing that really stays with me to this day is the pumpkin soup we always had, the smell of it, and waiting up for midnight for gifts.”

Over the years, apartments have come and gone, along with roommates and creative positions held at Sean John and DKNY. With his current bachelor pad in Gramercy Park, Osborne and his family also share a property in Westchester, New York’s New Rochelle, that serves as a communal hub during the holidays. Photographs, unique objects and keepsakes collected by his family render the tree-lined property not just a series of rooms but a home. “It’s a collective space,” says Osborne, “a collection of our travels, memories and everyone bringing these moments together in one home.”

And when it comes to hosting, he’s adamant that communal experiences should ignite the senses, with food, libations, music, lighting and aromas carrying the energy of the night. “Even when I host events for Public School, my initial thought is, ‘How can I try to do something special and memorable — something that’s different than expected?’ If you’re enjoying a glass of The Macallan [Double Cask 18 Years Old], what other elements are making that experience memorable? Can we make you smell something or see something that elevates it?”

After a six-year hiatus, Public School is returning to its throne, and to mark the soft launch, Osborne and Chow hosted a 2025 Supper Club at Manhattan’s Saga, replete with A-list fixings and a dining course prepared by renowned chef and restaurateur Charlie Mitchell. “With this space, we knew that the elevator and that whole process were going to be a thing, that people would be eager to come up. So we staged a magician downstairs, a comedy set and a jazz band so people wouldn’t feel they were waiting. We were thinking about those small moments that can make somebody’s experience that much more memorable — something that would last well after.” It’s a sentiment similar to The Macallan’s, that cherished moments should arrive in spaces curated with intention and thought.

Public School is slated to showcase its first collection in February 2026, with Osborne and Chow cooking up the label’s signature streetwise denim, pants, slouchy shirts, and ball caps that flip the script on luxury. But when asked how he takes a step back from it all to recharge, his at-home ritual sees him reconnecting with his vinyl collection and peeling away from digital screens. “It’s a simple thing of putting my phone on the charger, separate, away from my bed. It puts my mind at ease. I’m currently reading Essentialism, and it’s really about the simple things: journaling and reading things that are pre-Internet before you go to sleep.”

As for his approach to the gift-giving season, he prefers to plan months in advance. A whisky drinker, he’s fond of decorative bottles that amplify his bar cart, and he prefers The Macallan Double Cask 18 Years Old served on the rocks. “A great gift, really, is [the concept of] paying attention. It’s being thoughtful and paying attention to the people you love and making sure that they feel heard — knowing someone’s habits and the things they enjoy doing.” From watch winders to pop culture plushies, another one of his favorite gifts from a friend is a 45 vinyl of Garnett Silk’s song “Mama.” “I think it’s hands-down the best song devoted to a mom. I’ve been meaning to frame it,” he shares. Like his family home, Osborne points out that the items that characterize one’s space should be powered by emotion, enshrining the connections that matter most.

An elegant gifting option for friends and family, The Macallan’s prestigious portfolio boasts the Timeless Collection, which offers fine whiskys aged up to 30 years. Get a glimpse into how Osborne taps into the holiday spirit in the video and galleries above. Stay tuned on Hypebeast to see more from The Macallan Edit, Curated by Hypebeast, a party series that’s coming to NYC’s Pearl Box starting Saturday, December 13.

Below, find the perfect gift this holiday season by browsing signature offerings from The Macallan Timeless collection.