I watched this jacket on Mr. Porter for weeks. After a while it went on sale, but I always hesitate pulling the trigger when shopping online so I let it be. When I finally decided to get it, they had sold out. Crushed, I wandered the streets alone crying into a Starbucks cup. Salvation came from Opening Ceremony, who had apparently had it this whole time. Even though it was full price, I convinced myself that divine intervention was at work. Unluckily, it went on sale a few days later but that’s just the way shit goes I guess. Jacket, Carven; Shoes, Puma

I used to play with that typewriter at my grandfather’s house when I was wee lad. After he died, my grandmother had it fully restored and gave it to me in working order. It serves as a good reminder of him and I’m sure I’ll have it for years. The shoes on the floor are the ones I usually wear all throughout the summer. They smell like barf. A sprinkling of baby powder in them will keep the stench at bay and keep your feet dry—a tip from my mother. Shoes: Church’s, Superga, Hiroshi Tsubouchi, New Balance

Last year we threw a party at Lucky and invited The Bumbys to come and do their style appraisals. Standing in front of a masked stranger who’s pounding away on a typewriter is awkward, no question. But if that’s what it takes to have somebody say I could be either a tennis instructor by day, a private eye by night and an after-school instructor for mentally challenged grade school kids at a Hebrew school, then so be it. Glasses, Warby Parker

A really good friend of mine bought me these shoes for my birthday. She knew how much I like Rachel Comey and surprised me with them. They’ve held up real well and are very beat up now. A few weeks ago I was cooking some steaks and spilled half a pan of hot oil on them. It was kind of painful but they have a lot of character now and they smell like garlic. Delicious shoes. Shoes, Rachel Comey

I majored in printmaking back in college and although I don’t have the luxury of a full lab, I can do a little bit of work in my apartment. Inside this box are all the secrets of the world along with my carving tools. Those metal letters are from an old printing press; I found them in a shop around the corner from my house.

There’s a really diligent store associate uptown who sends me picture messages of anything that comes into the store that he thinks I’ll like. I can’t say I was exactly “in the market” for a V-neck collared nautical sweater, but you never know what you want till somebody texts it to you. Anyway, I wore it on a sailing trip once and ended up feeling like a complete ass. Take it from me; nautical stripes are better left to the land, weird as it may sound. Sweater, Michael Bastian

The piece up top is the first “real” piece of art I’ve ever purchased. I have never felt more mature than when I picked it up or scared carrying it around the city. Over the past year or so I’ve started spending less on clothes and more on artwork and home things. A friend of mine calls it “cheating on your closet with your home,” which feels appropriate. The steak print is by Timmy McSweeney, he works in the art department at Bon Appetit and has a good knack for design and screen printing. Hat, Harding Lane x Opening Ceremony

I get a lot of flack for this coat, but it’s one of my favorite outerwear pieces. First, it makes me feel like I’m on Game of Thrones, which leads to Live Action Role Playing (LARPing) around the city. Second, I like to scare strangers by casually mentioning that while hunting over the holidays our dogs returned with a coyote and we thought, “Why waste it?” Finally, it keeps me very warm all winter long and it’s something I know I will wear for years to come. Coat, Billy Reid

I sleep easier knowing that if a burglar broke in to my apartment, they wouldn’t be able to find my iPad on my desk because of this camouflage situation. They could hurt me, but they’ll never find my iPad. iPad Case, Jack Spade

In the spring and summer, I always carry a backpack or a bag. I know the backpack thing makes me look like a teenager, but it’s the most convenient way of toting all my crap around the city. One day I saw this on TresBienShop.com and sort of blacked out and bought it. The leather has oiled up very nicely and it also reminds me of the wallpaper in my bathroom at home, so that’s nice. Backpack, Yuketen

When I was a kid my grandfather used to buy us these balsa wood model airplanes and we would fly them around the yard. This plane was in an antique store by my house and got me all nostalgic, so now it sits on my fridge. That “to do” list was a gift from my friend Sarah who lives down the street, always crack a smile when I see it. Hat, Jack Spade x Coca Cola

Just in case anybody forgets what this room is for. Sweater, The Elder Statesman

I bought this scarf to celebrate getting my job at Lucky. Of anything I own, people ask me about this the most, saying it’s clever or pointing out the spelling error (which is on purpose). That blanket is from when I was aboard the Titanic. That was a weird night. Scarf, Michael Bastian

Skateboard, Céline

The dinosaur sweater is something I had my eye on since seeing the Jil Sander show. After Raf Simons announced he was leaving I felt like I wanted to get one last thing from his time there. My brother apparently felt the same and has the green one with a whale on it. We joke that it was to be our family Christmas card: “A very Jil Sander Christmas” or something. Sweater, Jil Sander

Obligatory holiday sweater for the holiday times. Sweater, APC

A couple of months ago I started using grooming products from Ursa Major. I have intensely sensitive skin and as far as I can tell, it’s the gentlest collection out there. I highly recommend it to anybody with the same issue. These are all books I’ve collected over the years, some are written by friends of mine, some are from college, but my favorite is probably the book of tweets on top of the stack. Perfect gift for anybody who likes to fill human relationship voids with social media. Twitter book, Ether-Press