If you own it, wear it.
“I’ve worn everything in my closet… Just because something is a couple years old doesn’t mean it’s dead to me. Everything eventually comes back in style in one way or another.”
Embrace your inner Carrie Bradshaw.
…when it comes to footwear, anyway. “Wearing a cool pair of shoes was not necessarily acceptable for guys 10 years ago, but now it’s actually okay for guys to have more than five pairs. Try patent leather or a colored suede loafer.”
A cross-country flight is a public space, not a sleepover. Dress accordingly.
“I do believe in airplane outfits, but I just don’t understand why people need to dress like they’re going to a pajama party to be on a four-and-a-half hour flight.”
Get to know your tailor.
“I can’t stand the shoulder pads of a suit hanging off of a guy with the bottom of the jacket at the knees. That’s kind of my quest, to get everybody to spend a little bit of money getting their suits properly tailored. At the very least buy a suit in your true size… not your dad’s size.”
Invest in cashmere.
“Everybody should treat themselves to one item of cashmere every winter, whether it’s gloves, a scarf, a sweater, or a pair of socks. It’s a very luxurious way to stay warm.”
“Every guy should invest in a really good overcoat, and all the accoutrements that go with it—a scarf, a hat, gloves, sunglasses. How can you relay your personality to the outside world and stay warm when there’s a blizzard going on? I think that’s the ultimate fashion challenge this winter.”
“You don’t have to stay stuck in a style. I don’t feel like I have to wear a cricket sweater and a bow tie every day. I can dip my toe into playing with color, or minimalism. Sometimes it’s even fun to be the edgy rocker guy. Putting on an outfit every day is a way of expressing how you’re feeling in the moment. It depends on how you want to portray yourself from day to day.”