Algonquin Park is one of my absolute favorite places on earth. It’s the landscape I miss most when I’m not in Canada. The Roots gang are like family to me in Toronto and they speak so fondly of Tamakwa. This T-shirt lets me pretend I went there, too! Striped Shirt, GAP; Tamakwa T-Shirt, Roots; Belts, Unknown Designers

The belt is vintage alligator from Kensington Market in Toronto. My favorite bookstore has to be Daunt Books in Marylebone, London. Sunglasses, Alexander McQueen; Belt, Vintage

The hat is my best mate—Brad’s—father’s company. I’m a dirtbag at heart, and this hat goes everywhere with me. The pillow was a birthday present from my “craftiest” friend, Martina. Hat, Bowes & Cocks Real Estate

The shoes have been everywhere with me and pack flat, so they're perfect for traveling. The candle’s from Chateau Marmont; love staying there, and love the scent. The L.A. Palms photo was taken by a friend, and the second photo is from an incredible holiday in Connemara, Ireland, with three of my closest friends. I miss them, so like having these pictures nearby. The antique lamp is a St. Lawrence Market find. Shoes, Onitsuka Tiger; Belt, Unknown Designer

I’m originally Canadian and came back to Toronto to help set up the Soho House. This city has changed so much (for the better) since I left, after finishing high school. It was great being back and crashing in my friend’s loft in Leslieville—a neighborhood that didn’t really exist when I last lived here. I stay in our hotels when I travel for work. Keychain, Alexander McQueen

The photos of my friends are from random party photo booths. Sunglasses, Persol

I’ve become addicted to Toronto-based label 18 Waits (as well as Roots, which I missed living in the U.K.). I also tend to spend far too much time at Te Aro in Leslieville and Grand Electric in Parkdale. Necklaces, Shaun Leane; Bracelet, Hermès.

I just fell in love with the Danko hat, which I’m not sure if I feel cool enough to pull off but am gonna give it a go anyway. Checkered Shirt and Striped Cardigan, Prada; Grey Cardigan, Alexander McQueen; Black Hat, 18 Waits; Cream Hat, Hudson's Bay Company

Flying lets me catch up with life: films I’ve been meaning to watch, books I’ve been meaning to read, or answer e-mails I’ve been ignoring! My carry-on essentials are: my iPod, cashmere scarf/blanket, a good book (I’m old school; no Kindle for me!), lip balm, water and Ambien. Brown and Beige Totes, Roots; Striped Bag, Gucci

These are your best friend during an English or Canadian winter! They smush into nothing and travel everywhere with me. I’ve lived in London most of my adult life and consider it home. A few favorite London spots include Barrafina, Columbia Road Market (go early), Bistrotheque, Cecconi’s and 69 Colebrooke Row for cocktails. Slippers, Atelier Da-No

Christopher and his sister, Tammy, are two of the absolute nicest people you could meet—or be lucky enough to share an adult beverage (or several) with. This is a men’s T-shirt version of his Mandrill dress from 2009. T-Shirt, Christopher Kane

Kiehl’s and Aesop are favorites. I also became addicted to Lucas' Papaw when I lived in Sydney. Notebooks, Smythson; Wallet, Comme des Garçons; Belt, Gucci

A general uniform can be as simple as jeans and a great T-shirt. Luckily, the company I work for frowns on formality, so suits are saved for special occasions. Tie and Scarf, Alexander McQueen

These bags never die and just get better with abuse. When the Soho House decides to open in a new city, I’m one of the first people sent out to get to know the city, the creatives that live there, and determine who we want to involve in the House. Also, during events such as the TIFF or Art Basel Miami, where we have a substantial amount of members involved, I work with a team to put together and host pop-up events. Bag, Mulberry

This is pretty serious artillery! It’s a proper weapon and has made a few people bleed. Vertebrae bracelet’s by my dear friend and one of the funniest people I know…as well as one of the most talented. Bracelet, Shaun Leane

Silver and Black Tie, Roland Mouret; Scarf, Alexander McQueen

I’m a cashmere junkie! Living in the U.K. for so long I developed a serious addiction to knitwear. I tend to favor either really thin cashmere or chunky grandpa cardigans. I buy most of it off mrporter.com, which I love; what’s better than having it shipped to your door!? I left for the U.K. when I was 19 and never looked back. But then every year I’d visit to see family, and later to host TIFF events, and I almost didn’t recognize the place. Setting up the Soho House here, I have to say I’ve met the most amazing group of people that are doing incredible creative things. Sweaters, Various Designers

I’m generally always on the move so I try to keep it simple and take as little as possible. My top five essentials are: A great jacket: I have a Roland Mouret one that I can pretty much crush into a ball and always looks great; my cashmere scarf (I’m always freezing on airplanes); good jeans (I wear them almost every day); flip flops/slippers to run around hotels in; a great carry-on/overnight bag. I try to only travel with hand luggage. Clothing, Various Designers

This phone is both hilarious and useful. I spend far too much time on the phone, and it’s nice not to be holding my mobile up to my head for hours on end. Wallet, Comme des Garçons

Ring, Shaun Leane

The vintage suitcase was a gift. The scent is Tuscan Leather. It used to give me the worst headaches, but I forced myself to get used to it because I think it smells incredible. Sunglasses, Alexander McQueen; Belt, Vintage

Although I’m prone to drink almost anything, I’m partial to either champagne or beer—I grew up in Ontario, after all. Shoes, Christian Louboutin; Black and Silver Tie, Roland Mouret; Painted Tie and Scarf, Alexander McQueen

These are custom trainers (I can always find them!). Can you tell I’m addicted to these notebooks?! Magazines I’m sure to pick up include Fantastic Man, W, Interview, Vanity Fair and 10Magazine. Shoes, NIKEiD; Sunglasses, Alexander McQueen; Notebooks, Smythson

These were from the first McQueen men’s show I went to: Spring 2007. The detail is incredible, and they remind me of our shenanigans in Milan. All, Alexander McQueen

Boots, Alexander McQueen

This was a birthday gift from Shaun—lucky boy! Necklace, Shaun Leane

Sweater, Hudson's Bay Company; Shoes, Nike

Jacket, Alexander McQueen

Scarf, Alexander McQueen

Jacket, Alexander McQueen

Jacket, Alexander McQueen