I am obsessed with my Sebago school loafers. Less than $100 at Bloomingdales last year and I can't get out of them. They remind me of being in middle school where my love for all things preppy probably took hold. All, Various Designers

All, Various Designers

The one pair of shoes I couldn't part with is the Raf Simons black boots on the floor all the way to the right, with no laces. I wear these everywhere, with everything. A close second are my oxblood YSL boots. Beaten up to perfection. When I went to college, I broke out of my Yeshiva dress code of preppy collared shirts and chinos and did the 90s grunge thing. Lots of flannel shirts and tons more Doc Martens. Now that it's back, I am staying far, far away. When I moved to New York, I chased every trend for about five years. They couldn't keep me out of Antique Boutique. But now I stick to well-made preppy classics in navy, navy and navy. Though I do like a green or burgundy moment now and then. I loathe summer clothing, so if I can be in a chunky turtleneck and boots 365 days a year, I am a happy camper. All, Various Designers

My organizing tips? I live alone and having worked in a retail environment, I understand merchandising. Oh, and purge, purge, purge. All, Various Designers

Bottom shelf is filled with sweatshirts I wear as sweaters. No matter what store I am in, no matter what city, I end up in a dressing room with a nice grey, blue or red crew neck sweatshirt sweater to try on. I can never remember if I have one (or ten) at home. All, Various Designers

I am not a nickname kinda guy but if one name has stuck it's Foxy and while I don't lean toward slogan or graphic tees and sweatshirts, I saw this on Mr. Porter and had to have it. It's Aubin & Wills and kinda speaks for itself. Plus, it's essentially a grey sweatshirt sweater. A plus! The sneakers are Dior, and I lived in them for two years. They are the perfect TSA shoe because while they look like a lacing nightmare, there's a zipper up the back that makes for easy in/out. Sweater, Aubin & Wills; Sneakers, Dior

I bought [the blue shoes] with my friend Drew Elliot at this teensy boutique on the Left Bank and have yet to wear them. They feel a little One Direction to me. Red sneakers are New Balance. I remember meeting Tony Melillo back when he still owned Nova on the LES and he told me that New Balance sneakers were the best for men because they had a wide toe box and balanced everything proportionately. Never forgot that. Always wear a NB low-top. Thanks, Tony! Green Lace-ups, Mr. Hare; Blue Shoes, Philippe Zorzetto; Sneakers, New Balance

I am reading The Heart Is a Lonely Hunter and the tell-all about Scientology on the nightstand along with a stack of magazines that are quickly dating themselves. Shoes, Gucci

The Queen Elizabeth is by Lightness of Being by Chris Levine (2004). The three pieces to the left: One is a menu from when Chanterelle closed. They sold their menus from their archive, this one had been created by Matthew Barney. The cartoon girl is actually a blow up of a small detail from a photo that ran in The New York Times in the early 2000s. The story was about Disneyland Paris. The written piece is by Uruguayan artist Alejandro Cesarco, I was introduced to him by my friend Gabrielle Jepson who runs the artist mentor program for Rolex.

That jacket is actually part of an Hermés suit and the Japanese papier-mâché figures were a gift from my father who bought them at the gift shop at The Golden Door spa, where he goes for men’s week. A friend of mine who lived in Japan tells me you're supposed to marker in one eye and make a wish. When the wish comes true, marker in the match, I need to get on that. Jacket, Hermes; Bag, Goyard

The pattern on the Gieves & Hawke toe box is purposely irregular, they are dubbed the "buckshot " style. That's a stack of Cargo magazines from when I was Editor-in-Chief at Conde Nast. We put out 20 issues over three years. I still get Tweeted at from fans who miss it and wish it hadn't closed. It's sweet. Shoes, Gieves & Hawke

Glasses, Dior; Sweater, Dries Van Noten; Pants, J. Crew; Sneakers, Comme des Garçons x Jack Purcell

I got these very limited edition Nikes in a store in Antwerp, not realizing how rare they are. People stop me on the street in NYC whenever I wear them now. I am really a baker at heart, but I do cook. I am learning to make vegan dishes from this awesome site called the Well Vegan where they send you meal plans, grocery lists and recipes. I just made Miso Tempeh Avocado wraps with Kale. Sounds dry, but they were delicious. Sneakers, Limited Edition Nike Air Royal Matte Black Patent High Tops

The Dries Van Noten boots are cobalt outside and Kelly green inside and that lug sole puts me close to 6 feet. I love the elephant grey of the Calvin Klein bag. The photo is by Lori Nix who specializes in disaster scenes created with miniatures. I took this down for years after 9/11, but now it hangs in my bedroom. As for dream art, I would love to own a Julian Opie. He did these enormous portraits of Formula 1 race drivers for the Milan Railway Station –one of those, and the wall to hang it on. Boots, Dries Van Noten; Bag, Calvin Klein

That porcelain horse is from a trip to Berlin. My friend Julius Eulberg is fanatical about porcelain and introduced me to a wholesaler and I picked this up. I cannot believe I didn't lose a hoof in transport. The sneakers are Raf Simons and I got them at Colette during Paris Fashion Week. Blue and green again, my favorite. Sneakers, Raf Simons

I can't really wear green near my face —no green shirts or sweaters because I’m too pale. But, I love green so I try and buy other green items for my wardrobe. I got these green and white dunks when I was in college. And people tell me, you know, you're wearing Celtics sneakers, right? And I say, mmm, maybe, but I don't play basketball and they’re cute. I bought this DSQUARED² blazer last summer. The first item I ever bought directly after seeing it in a department store catalogue at Barneys.