Mr. Nick Wooster has been called an Internet superhero and the “alpha male of American street style.” Some fans even call him Woost God. He’s got upward of half a million followers on Instagram, and photographers hound him at fashion Week and Pitti Uomo. It’s safe to say he knows a thing or two about style.

Mr. Wooster can also boast (if he were so inclined) 30 years of experience as a fashion director and creative consultant at highbrow retailers around the world. So it’s safe to say he knows a thing or two about luxury.

Which is why his new collaboration with Brooklyn-based sneaker company GREATS is so exciting. From luxurious Italian craftsmanship to Instagram-worthy designs, these bold, playful shoes are made to be enjoyed. We caught up with him between promotional appearances for the Nick Wooster x GREATS collection to ask him a few questions about shoes, style and what every man needs in his closet.

What’s the philosophy behind this collection?

The philosophy behind this collection is merely something I’d want to wear, something I don’t have in my closet. And that’s true for any collaboration I’ve ever done or any article of clothing I’ve ever designed. A collaboration is an opportunity to make something I hope is a little bit different and a little bit unexpected. And always something that I want to wear.

Do you have a favorite? Or is that like picking a favorite baby?

Well, I’m not a parent and I never will be. But I imagine that, as a parent, you’re probably always going to favor one more than the other at a certain time. Let’s see. I love the animal prints. I love all three equally. But I also love the shoe that I’m wearing, the 3M dots in black. And I really like the pink one. It depends on what I’m wearing. But … yeah, I think the animal prints are probably my favorite. Today.

These are bold shoes. How do you recommend styling them?

Styling boils down to a simple formula: if everything is classic, like a white shirt and khaki pants, or a grey sweater and grey pants, then you can do something interesting with the footwear. Keep it simple on top and then you can experiment.

With those three animal prints, the entry one is the Royale. It’s a simple tie shoe that is totally understandable, but in a slightly aggressive pattern. The second way would be the Pronto runner in the multi-pattern. The Genoa clog is the most adventurous way to go. But with any of them I recommend that you keep your clothes super simple.

When you’re helping a man build a wardrobe, what are the foundational pieces you recommend?

It’s so not interesting, because it really boils down to basics. I tell guys to get:

• White and blue button-up shirts
• A polo
• Dark denim
• A good pair of chinos
• Cashmere sweaters in navy, grey and black
• A peacoat for the winter

That’s about all you need. Once you have that base, then you can start to experiment with something. It might be the shoes, it might be the T-shirt, it might be the belt. That’s another thing I recommend: one simple, really good belt.

Another thing I always say: buy the best you can afford. For most of my life I’ve been up and down with my ability to purchase. And when times are lean, you want those great things that you can always fall back on. So when you’re able to invest, get the best you possibly can in that moment. But don’t put yourself in jeopardy because of it.

What do you look for in a shoe?

Well, hopefully it fits. I’m not kidding. I’ve bought many shoes that don’t fit because I just had to have them. It never works out. Beyond fit, for me, it’s if it sparks an emotion. The emotion can be something super simple, like excitement over a perfect pair of black or brown shoes. By the way, if you find a good brown shoe, buy it. Brown is really hard to do well.

With sneakers, just buy the ones that fit the best. Once you find a style you like, you can splash out on materials like animal skin or a fluorescent color, or maybe pink, maybe something 3M.

But the shoe has got to fit and feel comfortable. If it doesn’t do that in the store, it’s not going to do that later. Trust me. I’ve learned this the hard way. [Editor’s note: see our Dress Shoe Fit Guide for tips.]

Where do you see menswear going right now?

The casualization of fashion has forever changed how we dress. The good news is that it’s more democratic and more accessible than it’s ever been. The bad news is that you can’t put the toothpaste back in the tube. I hear people say, “Oh, tailoring’s going to come back.” Eh. Probably not.

And that’s sad to me, because when I had my first job back in 1976, I wore a suit to work and to clean the bathroom and to mow the yard. That was what you did. And that was a little stupid. But it does make me sad that Goodyear-welted leather-soled shoes and tailored clothing don’t have the same resonance that they did 25 years ago.

But by the same token it means that we’re moving on. So menswear is and will continue to be more democratic, more accessible and more casual. That’s the reality of the situation. And I’m OK with that.

Nordstrom is the exclusive retail partner of GREATS. The Nick Wooster x GREATS collection is available for men and women online and in selected stores. For more about GREATS, check out our interview with brand ambassador and street-style heavy Josh Peskowitz.

Photo credits: Kris Wilson, Will Griner