Sunglasses, Dries van Noten, Paul Smith, Super

I've had the Paul Smith tortoise shell glasses for more than 20 years and I'm sure I'll have them for another 20. L to R: Glasses, Super, Dries van Noten and Paul Smith

Shoe, Pierre Hardy

Bottom to Top: Sweaters, Prada, Lanvin, Marni, Margiela and Jil Sander

Think we are subconsciously nostalgic and are drawn to things from our past. Growing up beside the ocean in Canada, you're guaranteed to have a good base of sweaters in your wardrobe—particularly wool. The scratchier and coarser, the better. L to R: Sweaters, Prada, Lanvin, Marni, Margiela and Jil Sander

I love desert boots in any color. The more worn in, the better. Shoes, Clarks

The pin was bought at Holt Renfrew for a formal event and I wore it with a suit. I still wear it on the odd jacket but also on T-shirts. I am originally from the Maritimes and a big sailing family so it has a bit of sentiment attached to it as well. Pin, Prada

Sweaters, Various designers

Watch, Vintage Rolex; Pin, Lanvin; Neckpiece, Prada

My partner, Boris Masip, gave this watch to me for my birthday. It is my most special and coveted possession. I didn’t really want a "serious" watch unless it was vintage and not over-designed in its look. Boris surprised me with it last year and I am absolutely in love with it, particularly the champagne face on a generic style body. Watch, Vintage Rolex

You will always see me with a backpack on my back. I am pretty utilitarian with my bags. I put them through a lot of wear and tear and am also always lugging things around. The tote is for meetings when I need to look more polished. The last one, the canvas one, is a great day-to-day bag, that looks lived-in which I love. Backpack, Comme des Garçons; Tote, Prada; Canvas bag, TK Garment Supply

What I like about the two is mixing the raw and refined. The shirt is completely deconstructed with threads hanging off it and the neck piece reminds me of something from Edwardian times. I love the contradiction. I’ve always been a big proponent of contradictions and dichotomies in style. The photo is by Serge Leblon and is a picture of Vanessa Seward (of Azzaro) and her boyfriend, Bertrand Burgalat. They are so chic and intrinsically Parisian. I love the subjectivity of the photo—are they devastated, bored, frazzled? Is it the beginning of the relationship or the end? I can look at that picture every day and every day, conjure up a new story. Shirt, Prada; Neck Piece, Prada

I am not an over-consumer of shoes. I don’t feel the need to own hundreds of pairs. That said, I am compulsive about the maintenance of them. Although I love things that don’t look precious or too new, I do like them well-groomed. Our shoes go out every Saturday, in bulk, to get professionally shined. We are always only dealing with half our assortment as Robert at Novelty Shoes has the other half. Shoes, Prada, Rachel Comey, N.D.C., Pierre Hardy, Lanvin

I've realized that I have a complete fixation with grey—although, I do love strong and bold colors as well. I’ve never met a shade of grey that I don’t like. Sweaters, Marni, Margiela and Jil Sander

I am not that attracted to suits. I love them on others, but personally, I prefer a jacket and pants. I like to mix it up, so have a lot more jackets and pants than suits. I like my jackets to have a higher armhole, shorter sleeve, pinched waist and a smaller shoulder. With the exception of the navy one, you can see my predisposition to grey. Suits, Prada, Dries van Noten, Prada, Dries van Noten, Comme des Garçons, MargielaSuits, Prada, Dries van Noten, Prada, Dries van Noten, Comme des Garçons, Margiela

I like items that stand alone—either in the fact that they are bold with one characteristic or just damn good design. The fun part is to mix them up and make a new concoction each day.I like items that stand alone—either in the fact that they are bold with one characteristic or just damn good design. The fun part is to mix them up and make a new concoction each day. Scarves: Sophie Prieur, Burberry Prorsum; Sunglasses: Super, Dries van Noten; Belts: Marc Jacobs, Brave, Prada, YSL; Sweater, Lanvin; Top, Prada

I think Rachel Comey is incredibly talented. I buy as many pieces per season as I can. Shoes, Rachel Comey

The photo is of Kirsten Owen and again, is a bit of a contradiction in that the expression is so candid and the fashion is so tailored. It is completely subjective in terms of what she's doing—yelling, yawning, freaking out, overdosing? I just love the juxtapositioning in this picture. Shoes, Prada, Rachel Comey, N.D.C., Pierre Hardy, Lanvin

The picture was taken by Chris Nicholls when we were shooting a Holts book in New York a few years back. We were in the Meatpacking District when I saw this vista and asked him to shoot it in between shots of the model. People often think it's a collage but it's an actual picture. The woman in the photo was a piece that Shepard Fairey had plastered on the front of the building (much before his fame with the Obama posters). Chris shot a few frames before this screaming transvestite came running out of the door (that is obscured behind the clothes) and starting freaking out about us shooting his door, yelling something about respect. Makes for a good story when my partner, Boris, and I have friends over for dinner. All, Lanvin

L to R: Belts, Marc Jacobs, Brave, Prada, YSL

The boots are L.L. Bean and like my glasses, I will have them forever. I walk everywhere and in the winter, they are perfect for trudging through the city. In university, I was a die-hard New Wave’r but in high school, I was a hardcore prep—always in Polo, Lacoste and L.L. Bean. With these boots, I’ve come full circle again. Shoes, L.L. Bean

Shoes, Rachel Comey

I think Virginia Johnson is brilliant. I don't wear scarves that often; I usually prefer them for more formal occasions. I have built up a bit of a collection and always swear I am going to wear them more. (Maybe a New Year's resolution in the making?) The rosary was bought it Tulum, Mexico and stands about six feet tall. Tulum is a very special place for me—it has a spiritual quality to it. I have made some magical moments in Tulum. Scarves, Virginia Johnson and Number Nine