Outdoor Boys Series: Tomato Soup + Grilled Cheese Sandwich Recipe

Daniel
Aug 4
3 min read

Updated: Sep 30

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.

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

Equipment:

Cast Iron Skillet / Pan
Heavy Pot
Blender / Hand Blender
Oven

Directions:

Please visit my "How To Make Shokupan" page for the easy flatbread recipe.
Roast the Tomatoes
Preheat the oven to 180°C (355°F).
Score a small “X” at the base of each tomato and remove the tops.
Place tomatoes in a baking dish, drizzle with 2 TBSP of olive oil, and season with salt and pepper.
Roast for 20–30 minutes until lightly charred.
Make Simple Veggie Stock
Simmer your leftover veggie scraps in 1L of water for about 8 minutes, then let steep for another 8.
Strain and set aside.
Cook the Soup Base
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.
Add sliced fennel and tomato purée, followed by a splash of veggie stock to deglaze.
Stir in garlic and celery seeds, then butter and flour to thicken.
Add the Tomatoes
Pour in both the hand-crushed canned tomatoes and the roasted tomatoes.
Deglaze the roasting pan with stock and add that too.
Let everything simmer, and adjust seasoning to taste.
If too thick, add a bit more stock; if too runny, reduce by simmering longer.
Blend using a hand blender or standard blender until smooth.
You can pass the soup through a sieve and discard the fiber residue.
For a rustic feel, leave it slightly chunky like I did.
Make the Grilled Cheese
Mix the three cheeses with chili flakes and pepper.
Butter one side of each bread slice.
In a skillet, melt some butter and place bread butter-side-down, layering with cheese.
Top with the second slice, buttered side up.
Press gently, cover, and cook until golden and melty on both sides.
Optional Infused Oil
Gently heat olive oil with sliced garlic.
Once the garlic starts to sizzle, remove it from the heat.
Add in chili flakes and Italian seasoning. Swirl to combine well.
Drizzle this over your soup just before serving.
To Serve
Pour the soup into bowls, garnish with fennel fronds, and a drizzle of infused oil.
Serve the grilled cheese alongside, sliced on a bias, perfect for dipping.