Expect nothing less from the son of Mad Men producer Matt Weiner.
This is my Valentine’s Day outfit. The jacket and the pants are velvet. I love the tie because it’s really two ties stacked on top of each other. (My dad had to tie it for me.) The pink tie matched the pink shirt. I wore brown-and-white argyle socks for a random pattern.
My mom got the jacket for me—I love it because I love Frank Sinatra and this is like something he would wear. I wore the jacket with the pants because I like the different plaids together. I thought the blue in the necklace brought out the blue in the pants. It’s a blue orb with fire around it.
I have a lot of black outfits these days, so I needed the red ascot to add some color. I love red and black together—they each make the other stand out. I’ve worn this to school about 12 times.
I was going to play miniature golf with my brother Charlie. You can see how much I like to mix patterns. I love argyle—I was wearing argyle socks, too. The red ascot brings out the red in the pants. The only thing I was unsure of was whether the shirt would be weird with the rest of the outfit, but I wore it anyway because it was too hot to wear long sleeves. The hat used to be my dad’s.
We were going to Getty Village and then having breakfast on the beach. I wanted to wear black and white. Most of my ties, like this one, are clip-ons.
The hat is like a Frank Sinatra hat. I wore the jacket with the tie because green and gray are my favorite blend. I’m holding my dad’s bag in the picture, but at school I use my dad’s old brown leather satchel.
I love this red jacket. I wore the black shirt underneath because I really like red and black together. I got the jacket and pants in New York—we did a lot of shopping in New York.
I thought the sunglasses would go well with the pants because they’re both gold. The tie on my neck—that used to be the belt for my bathrobe, but I shortened it and turned it into that. I put the tie with the jacket because I liked the patterns together. My grandma gave me the cane. I thought it looked good with the pants.
I like to put random patterns together, so I picked out the green checkerboard tie with the gray checked jacket and then I wore the red vest underneath, because red stands out and brings the colors together.
This is my favorite outfit. The tie is a regular tie, but I tied it like that because I’ve seen it done that way in old English movies. Even though the tie and the jacket are different colors, they’re both striped, so I thought they looked right together. And I wore the vest and pants together because they’re both shades of red.
From men.style.com