Outdoor Boys Series: Tomato Soup + Grilled Cheese Sandwich Recipe

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There’s something timeless about grilled cheese and tomato soup. I first got the nudge to finally try my own version after watching Luke from Outdoor Boys sip on canned Campbell’s tomato soup by the fire, pairing it with a golden grilled cheese sandwich.

Just outta the oven...

It made me realize as many recipes as I’ve shared, I somehow haven’t posted this classic combo. With tomatoes in season, this felt like the perfect moment.

The dish itself has humble roots. Tomato soup dates back to the late 19th century when it became a staple in American homes, especially with the rise of canned goods. Grilled cheese took off in the 1920s and 30s when sliced white bread and processed cheese became common pantry items.

Put the two together and you’ve got a match made in culinary heaven, warm, creamy soup with crispy, melty sandwiches. Over the decades, it’s evolved into comfort food royalty.

I’ve given mine a slight twist with fennel, homemade stock from veggie scraps, and a finishing touch of infused oil. It’s rustic but layered with flavor, sweet roasted tomatoes, mellow onion and fennel, that bit of tang from tomato purée, and the richness of butter and stock.

And the grilled cheese? A gooey trifecta of mozzarella, Gouda, and Parm, kissed with chili flakes. You get a little heat, a lot of melt, and just enough crunch to dip or enjoy on the side.

Whether you’re feeling nostalgic, cozy, or just craving something simple and satisfying, give this a go.

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Ingredients:

(Serve 4)

• Soup:

• Fresh Tomatoes, 800g

• High Quality Olive Oil, 2 TBSP + 2 TBSP

• Sea Salt, Pinch

• Black Pepper, Pinch

• Yellow Onion Thinly Sliced, 1

• Fennel Thinly Sliced, 1 Bulb Reserve the fronds for garnishes

• Tomato Puree, 2 TBSP

• Garlic Finely Minced, 3 Cloves

• Celery Seeds, 1 TBSP

• Unsalted Butter, 2 TBSP

• Unbleached All Purpose Flour, 2 TBSP

• Canned Tomatoes Hand Crushed, 800g

• Grilled Cheese:

• Low Moisture Mozzarella Grated, A Handful

• Gouda Grated, A Handful

• Parmigiano Reggiano Grated, A Handful

• Black Pepper, Pinch

• Chili Flakes, Pinch

• Unsalted Butter, For Spreading

• Shokupan Homemade / White Sandwich Bread, 8 Slices

• Infused Oil (Optional):

• High Quality Olive Oil, 1/4 Cup

• Garlic Thinly Sliced, 1 Clove

• Italian Seasoning, Pinch

• Chili Flakes, Pinch

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Equipment:

• Cast Iron Skillet / Pan

• Heavy Pot

• Blender / Hand Blender

• Oven

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Directions:

1. Please visit my "How To Make Shokupan" page for the easy flatbread recipe.

2. Roast the Tomatoes

3. Preheat the oven to 180°C (355°F).

4. Score a small “X” at the base of each tomato and remove the tops.

5. Place tomatoes in a baking dish, drizzle with 2 TBSP of olive oil, and season with salt and pepper.

6. Roast for 20–30 minutes until lightly charred.

7. Make Simple Veggie Stock

8. Simmer your leftover veggie scraps in 1L of water for about 8 minutes, then let steep for another 8.

9. Strain and set aside.

10. Cook the Soup Base

11. In a heavy pot, heat 2 TBSP of olive oil and sauté sliced onions with a pinch of salt and pepper until soft and caramelized.

12. Add sliced fennel and tomato purée, followed by a splash of veggie stock to deglaze.

13. Stir in garlic and celery seeds, then butter and flour to thicken.

14. Add the Tomatoes

15. Pour in both the hand-crushed canned tomatoes and the roasted tomatoes.

16. Deglaze the roasting pan with stock and add that too.

17. Let everything simmer, and adjust seasoning to taste.

18. If too thick, add a bit more stock; if too runny, reduce by simmering longer.

19. Blend using a hand blender or standard blender until smooth.

20. You can pass the soup through a sieve and discard the fiber residue.

21. For a rustic feel, leave it slightly chunky like I did.

22. Make the Grilled Cheese

23. Mix the three cheeses with chili flakes and pepper.

24. Butter one side of each bread slice.

25. In a skillet, melt some butter and place bread butter-side-down, layering with cheese.

26. Top with the second slice, buttered side up.

27. Press gently, cover, and cook until golden and melty on both sides.

28. Optional Infused Oil

29. Gently heat olive oil with sliced garlic.

30. Once the garlic starts to sizzle, remove it from the heat.

31. Add in chili flakes and Italian seasoning. Swirl to combine well.

32. Drizzle this over your soup just before serving.

33. To Serve

34. Pour the soup into bowls, garnish with fennel fronds, and a drizzle of infused oil.

35. Serve the grilled cheese alongside, sliced on a bias, perfect for dipping.

Mama Mia...

All that ooey gooey goodness...

Hearty and yummilicious...

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Recipe Video: