Clay Patrick McBride shot this spread and when he first showed me his portfolio there were a few photos that I fell in love with. He is an awesome guy and actually sent me three of his pieces the next day. This shot is from a spread of Jay-Z re-enacting the Kennedy White House years in the Oval Office. Shoes, Nike

My mom grew up riding and my parents have a summer house in Santa Fe, New Mexico. They got obsessed with Lucchese boots and made friends with the guy who owned the store, so of course I thought it was necessary to buy three pairs when I went to visit them. Cowboy Boots, Lucchese

I got the Supergas last summer after a top fashion blogger told me I should get a pair. I love my Chuck Taylor's, but the Supergas have that European edge to them. My Mom bought me the Tag watch for my Bar Mitzvah. I get the most compliments on [the Casio] watch. The black on black Nixon is one of my favorite watches. Shoes, Superga; Watches (Clockwise From Top): Nixon, Tag, Casio

I'm not a big drinker; I like a good scotch or tequila. The Veuve was a present from my best friend and business partner, Doug Imbruce. I have the feeling we will popping it at a celebration soon. Shoes, Grenson

Organization keeps me sane. I love things in order; it alleviates a lot of the stress of getting dressed. Good shirts are surprisingly hard to find, but after years of searching I've found some secret spots for shirts that fit perfect off the rack: J. Crew's Men's Shop, Topshop, Seize Sur Vingt for when you want to class it up (courtesy of Gilt Groupe to rationalize the price) and my favorite spot for shirts, Uniqlo. If anyone has other places for great shirts... let me know! Shirts, Various Designers

I have a good friend and business partner who taught me the art of the tear sheet. He's one of the more logical people I know. He said just find pictures of looks you like, tear them out, and match the look for the day. It was my secret…till now. A lot of guys can rock a nice tie or a nice piece of anything for that matter, I like things with a little edge, a little story behind them, that's what's cool about vintage. I've always loved just a little something subtle to differentiate. Ties, Various Designers

My earliest memories of my grandmother are in the shoe department at Saks. Maybe it's genetic. A strong Nike collection is a must. Boat shoes are part of my May-September uniform and I think all men should rock handmade British dress shoes. Shoes, Various Designers

My best friend got me this Stewie doll. He would actually make a great receptionist. We should probably see if he's looking for a job; he'd be great at StyleCaster. Belts, Polo by Ralph Lauren

I'm pretty brand loyal and Topshop is one of my favorites as you can tell. London has nailed the art of the trench. This and my Burberry trench are two of my favorite jackets. Jacket, Topshop

There are few things that make me as happy as my Nike College Basketball shorts collection. A new pair is the fastest way to my heart. Anytime I am in a college town I always pickup a new pair. As a sports fanatic and marketer, Nike is just one of the greatest brands you could ever imagine. The book is one of my favorites; it's a signed copy by the author and it's the story of Phil Knight and the guys who started Nike. Shorts, Nike

I get one new pair of Sperry every summer. I live in boat shoes when it's nice out. And these have safety pins in them – you can't beat that. One of my most prized possessions is my autographed book collection. I am a total book nerd. Susan is a fashion industry legend and when you meet her you understand why. She's amazing. Shoes, Sperry x Band of Outsiders

These are one of my Dad's favorite things in the world and a few years ago he gave them to me. They are my first baby shoes, and they are also the first ever Adidas baby shoes. My uncle who was a higher-up at Adidas at the time was one of the main reasons I always wanted to go into sports marketing. Shoes, Adidas (First Adidas Baby Shoes Ever Made)

The boots are limited edition Sebago and were a recent purchase this winter, I love them. There's just something about them, I love the red laces. The real staple though is the Ray-Ban Aviators. The Aviators are classic, timeless and make everyone look cool. I'm not that cool so they help the cause. Boots, Limited Edition Sebago; Sunglasses, Ray-Ban

The tie is one of the most special things I have. It was a birthday present from my ex-girlfriend who was my inspiration for starting StyleCaster. Coming out of college there was only one guy I wanted to work for, Steve Stoute. Stoute is an amazing visionary and entrepreneur. He was impossible to find, let alone get a hold of, and I called and emailed for months until I finally got a meeting with him. It was one of the most important meetings of my life and I thought it would be cool to wear my first Hermès tie, I thought he might appreciate it. During the interview I was selling as hard as I could, this was the job I wanted, but Steve didn't say much. Finally he looked up and said, 'Ari, is that an Hermès tie?' And I said, “yes Steve, of course it's an Hermès tie.” I got the job and Stoute gave me my first break into the industry. My career, my inspiration for StyleCaster, everything is embodied in that tie. Working with LeBron and the team at LRMR was definitely one of the highlights of my career so far. I was brought on at the beginning to help start the agency, it was literally my dream job. Ever since I was five all I ever wanted to do was represent the greatest athlete in the world and at twenty-five I had the opportunity to do it. The LeBron action figure was a limited edition piece that Upper Deck did based on the Nike Commercials of 'The LeBrons.' Tie, Hermès

A friend got me this picture from The Morrison Hotel as a birthday present a few years back. Hendrix is not only one of the greatest artists to ever live but also a style icon. The bracelets look like something Jimi would rock. Bracelets, Topshop

Topshop gets it. The Brits just get it. The bike is Cannondale. One of my favorite parts of living in N.Y.C is the West Side Highway, just the ability to get out and run or ride on the water is amazing. Shoes, Converse; Bag, Topshop

I am just starting to learn how to wear my browns and beiges. Sweaters, J.Crew, Topshop

This is another picture from Clay's spread that features Jay and Kanye as JFK and RFK. I love this picture. The picture with Puff is from a Thanksgiving Eve event I produced in college that he headlined. What you don't see in the picture is my Mom who was there. When I introduced Puff to my Mom he looked at her and said, 'Man, that ain't your mom. That's your younger sister.' My mom still tells the story. Shoes, Nike

I've pretty much worn out the soles. The action figures are the full boxed set of the Upper Deck collection from Nike's 'The Lebrons' commercials. Shoes, Grenson x Rag & Bone