Clothes & Personal: Andy Spade

A few lessons on the art of dressing sharp and living well

By Shari Gab

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23 January 2018

They say the clothes make the man. But today, we’re talking to the man who makes the clothes. This is Clothes & Personal, with Sleepy Jones and Jack Spade chief Andy Spade.

Andy Spade likes to keep it casual.

The brains behind haute sleepwear label Sleepy Jones, Spade has been known to wear PJs in public and just published a photobook shot entirely on iPhone called Likes.

So we recently caught up with him for some insights on looking good while keeping it caj — right down to the dime-store pickup every man should keep in his closet.

Spoiler alert: they pair well with boats and coolers.

InsideHook: Tell us about your new book.
Andy Spade: What book? Oh, this book (laughs). My friend JP Williams, who you may know, always wanted to make a book out of my photographs from Instagram. It's called Likes. You know, the Instagram thing you push: Likes. It's a big, big book, and beautifully done by him with a foreword by my friend Glenn O'Brien, who sadly passed away recently.

IH: It’s pretty meta to do a tactile book based on a digital platform. What compelled you?
AS: Technology. There's too much of it, and I think it's just an addiction. I'm addicted to books more than I am to Instagram, and I love paging through them. So [this book] is like a vacation.  

IH: You’re a big bag guy [look no further than Andy’s first foray into menswear, Jack Spade]. Is there something men get wrong when it comes to everyday carry?
AS: I always thought that I didn’t like the wheelie bag, but it's practical. Now I've changed my mind: I would wheel a bag around.

IH: Is there an age where a man should be wary of dressing his age?
AS: Eighty, maybe? Eighty.

IH: Do fashion fellas take themselves too seriously?
AS: I think that men care too much about how they look, yeah. I mean, not everyone. A lot of men don't care at all about how they look, which is also equally terrible. But some people are always moving their hair around, or fixing their lapel. It’s not the most important thing in the world.

IH: What IS the most important thing?
AS: Children, I think. People, animals, our environment. Certain architecture.

IH: A few years ago, you started upscale pajama label Sleepy Jones. But has athleisure gotten out of control? Are people too obsessed with being comfortable?
AS: Can you really ever get too comfortable? I don't know if you can get too comfortable. For me, these pajamas came to be when I had my daughter and I'd walk around the house or I'd want to impress my delivery man. I know there's a whole leisure thing, which I know is overstated. I have like 50,000 men's shirts. The pajama shirt is a nice alternative to all the others.

IH: If you have that many shirts, who are the MVPs?
AS: I like my old vintage J. Press and Brooks Brothers. Hamilton also makes a really great one that I wear custom with suits to fit me because I'm … I'm fun-sized. That's a technical word for someone who's a 31” sleeve and a 15.5” neck.

IH: Anything in the style world you’d like to see go by the wayside?
AS: I'm not a fan of flip-flops. I’m not a fan of those Teva sandals.  

IH: So, no sandals?
AS: I do like the dime-store flip-flop, with the little rubber bottom. They cost like 99 cents, $1.99, green, red, blue, yellow. I love those. And they match your cooler, too, if you get the classical cooler, the Igloo. If you're concerned about color-coordinating your sandals to your cooler. I’m fanatical about it.

IH: Do you wear your Sleepy Jones out of the house?
AS: I do, I've worn the entire ensemble out. You know, just to run errands with the jacket. I've worn the shirt with a tie and sportcoat. I wear them around the house. I wear them at the beach. I wear them on boats. Like Green Eggs and Ham. (Laughs.) I wear them on trains, I wear them in planes.

But really, I was working with some clients and they were asking me like what the best brand of formal shoe is. For formal shoes, I said Alden’s. For casual shoes, there are so many I love — Vans, Converse. I love Sperry. But when they asked me about the best pajama, I couldn’t think of one. So I thought I’d fill the void.  

And the athletic thing was covered, you know? The athleisure thing's covered. So I'm just leisure. I don't have the ath-.

IH: Okay, some quickies. Mixing patterns, yay or nay?
AS: Yup.

IH: Canadian tuxedos?
AS: For me, no.

IH: Mismatching belts and shoes?
AS: Fine.

IH: Mismatching coolers and sandals? (I’m just messing with you.)
AS: No way. That's a good question. People didn't think about that. (Laughs.) I don't know why that's not in the style guides.

IH: Fake Rolexes?
AS: Sure.

IH: Statement tees?
AS: What are those?

IH: Like “The Future Is Female,” for instance.
AS: Oh, yeah, I like that one. I have one that says, "Stupid is a four-letter word." I like that. And there’s one that just says "Bill Murray.” I like Bill Murray, so of course, I'd like the shirt.

IH: Ironing your T-shirts?
AS: For formal events, yes.

IH: Ironing your underwear?
AS: Fluff ‘n’ fold.

IH: Cargo shorts?
AS: Not for me, but people who have to carry a lot of stuff, probably a good idea.

IH: I don’t think those dudes are actually carrying anything in those pockets.
AS: I thought that's what the pockets were for. What are they there for then?

IH: Aesthetic. They think it looks good — or so I think.
AS: Wow, I thought aesthetic was something else.

IH: What’s the best travel bag?
AS: The Jack Spade big duffel in waxwear canvas. I also like T. Anthony a lot. And I like Best Made Co.

IH: You just did a collaboration with Best Made Co., no?
AS: Yes, Sleepy Jones and Best Made together. We did a robe and a blanket.

IH: Last question, what’s next?
AS: Next is always just more, I’m designing a new collection for Sleepy Jones. It's going to be “inactive-wear” and we're doing inactive, eh, action figures. So, think little collections of toys of non-active people, like Mr. Sloth and Mr. Couch Potato. Instead of action figures, they just don't do anything.

And another book called Things I'll Never Do. And a TV show. It’s a series of documentaries called I Am. It's about different careers that people have today that they didn't have when I was growing up. When I grew up I thought you could only be a fireman, or a doctor, or lawyer, or a real-estate agent, or pro golfer, or skateboarder. But now there are so many different careers. So, it'll be just a day in the life of a copywriter, a day in the life of a coder, a day in the life of, who knows, maybe you.  

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