Off The Beaten Track: CalebThill - Grenson
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Interview

OFF THE BEATEN TRACK:
CALEB THILL

August 2026

Interview | August 2026

For this weeks Off The Beaten Track We caught up with our friend Caleb Thill from Brooklyn, NYC to talk about a few of his favourite things. From where to eat in New York and the city’s more overlooked spots, to Greek islands, far-flung surf breaks and some very good hotels. We also get his tips on travelling light, the brands currently on his radar and the wardrobe staples he can’t live without.

Where do you live and Work?

I live in NYC - specifically Williamsburg Brooklyn! I love so much about NYC! It truly is so many different and amazing cultures that blend together… The spontaneity of the city is unmatched, you can walk out of your apartment with no plans and end up having an incredible day!

Can you let us in on your favourite New York restaurants?

Four Horseman

Len Len

Do you have any ‘off the beaten track’ restaurants, bars or parks recommendations you can share with us?

  • Lhasa Fast Food in Jackson Heights for incredible jhol momo’s (Tibetan food!)
  • Jackson Heights in general is an incredible neighborhood in Queens that alot of tourists and even people who live in NYC overlook… It's the most culturally diverse neighborhood in the world! And its less than 30 minutes via subway from Manhattan.
  • Chang Lai for curry fishball noodles!! Get all the sauces!
  • Socrates Sculpture Park!!

 

Socrates Sculpture Park

We know you travel a lot, where are your favourite places to go and why?

Any chance I can get to visit random small islands in Greece, I take! It's such a beautiful country! I LOVE Sicily - specifically Favignana - a small little island 2 hours from Palermo!

You’re a big surfer, where are your favourite places to surf?

Some of my favourite places I’ve ever surfed are El Salvador, Morocco and the Maldives!!

You often combine activities with your travels and there is always an element of discovery to your travel, what have been the best places you have visited that covered this?

I had the time of my life road-triping through the Scottish Highlands and the Isle of Skye in a vintage Defender with a camper tent on top. Another trip that stands out is my surf trip to the Maldives! I was with a small group that rented a boat and we just explored all over finding waves, little islands and really just stayed on the boat for 12 days. Truly an insane experience!

Caleb wearing Quinton

Caleb wearing Sterling

As you are away a lot, do you have any packing hacks?

#1 tip is never check a bag unless you absolutely need to! I always try to bring just carry-ons so I can be flexible with my travels!

If you could live anywhere in the world, where would it be?

NYC right now tbh!! I mean, part of me dreams to live on the coast where I can surf every morning, but I think I’d get bored after 2-3 months! Internationally, maybe Lisbon? Great city with amazing and accessible surf close by! Who knows!

Are you a hotel or Airbnb guy? Can you let us in on some of your favourite ones you’ve stayed in?

Always a hotel!! Not in any particular order, but these are a few of my favs!

Maroma in Mexico

Kinloch Lodge

What are some of your favourite brands that may not be on our radar?

  • Anim living - a gorgeous Turkish brand that occasionally drops incredible menswear pieces!
  • Colbo - modern silhouettes and neutral palettes!
  • Very well known in the industry, but I feel like a lot of people still dont know about them - jacque marie mage sunglasses are the best splurge ever! I’ve had my pair for 5 years now and they still look brand new!

 

Anim living

jacque marie mage

Who would be your style inspiration?

The entire cast from the original Talented Mr Ripley! lol

Can you give us 3 of your current wardrobe staples?

  • A great off white flowy linen shirt for summer
  • A great pair of raw denim jeans - straight leg!
  • My cartier santos in navy
  • A great pair of loafers

What is it about Grenson shoes that work for your wardrobe?

They're so versatile! I can dress them up and down and they elevate any outfit! I love the sandals for summer too! I love wearing a fancy loafer with just a crisp white tee and a dark pair of jeans!

Do you listen to podcasts? Can you recommend your favourites?

I don’t listen to podcasts, but I can give you 3 books I’m loving

  • The secret history - Donna Tartt (the perfect beach read)
  • Yes, Daddy (exactly what you think it’d be lol)
  • The Great Believers by Rebekah Makai

Sterling

Sterling and Quinton

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