In the Kitchen with Jackie — Tomato Soup & Grilled Cheese

Hard to believe that summer is gone and it’s time think about fall flavors! Hopefully we’re all settling into our new schedules for work and school. In our house, meal times is the anchor for keeping dinner (and bed time) on track, so it’s definitely time to bring out all those easy, cozy and comforting fall recipes.

When thinking of my personal favorites, I landed on the quintessential intersection of ‘back to school’ and comfort food: tomato soup and grilled cheese! It’s a classic combo equally delicious and full of culinary nostalgia. Have you ever wondered when these two became as inseparable as peanut butter and jelly? Like many American food traditions, it started back after World War II.

Grilled cheese sandwiches were already popular within the army because they were inexpensive and met the minimum of nutrition standards. After the war, school cafeteria meals were becoming standardized to also meet these nutritional guidelines, but the beloved grilled cheese was lacking. It needed something else to round out the meal. Tomato soup is full of vitamin C as well as cheap and easy to prepare, so the pairing became a staple on cafeteria menus across the country. Luckily, they discovered a winner! The tangy acidity of the tomatoes plays against the creamy, buttery grilled cheese. 

My recipe is a hot take on the old favorite. First of all, I’ve pumpkin-ified the soup. Don’t roll your eyes! The pumpkin adds a welcome creaminess to the texture – without the use of cream – as well as an earthiness. It also acts as a thickener so no flour is necessary, as is the case with a ‘regular’ tomato soup recipe. The pumpkin can be from a variety of roasted squashes. I used a kabocha squash, but feel free to substitute with a simple can of pureed pumpkin. The addition of some fresh sage ties it all together into a delightful fall flavor profile. To complement these additions, I chose a hearty whole grain loaf of bread and meaty Gruyere . You can dunk sandwich triangles in the soup or try cutting it up into cubes and sprinkling them on top like croutons! Either way, I promise it will elicit the same cozy feelings and satisfied appetites. 

Tomato Pumpkin Soup with Grilled Cheese Croutons
Serves 4

Tomato Pumpkin Soup

1 can Bianco DiNapoli Crushed Tomatoes
1 cup of roasted pumpkin – i.e. kabocha, butternut, acorn
1/2 onion, minced
2 garlic cloves, sliced
2 cups Aneto Vegetable Stock
1 tsp fresh sage, reserve some for garnish
1 tsp Kosher salt
1 tsp ground pepper
Sicilian Extra Virgin Olive Oil, for garnish

Grilled Cheese
Makes 4 sandwiches

Loaf of whole grain bread
8 oz Gruyere, grated
1 oz Parmigiano Reggiano, grated
2 tbsp salted butter

  1. Sweat onions and garlic in a heavy bottomed pot, stirring frequently until translucent, about 10 minutes. Add salt and minced sage and saute for another 2 minutes. 

  2. Add tomatoes, pumpkin and broth. Stir and reduce heat to medium low to allow the soup to a low simmer for another 10 minutes. 

Blend the soup either using an immersion blender for a chunkier texture, or a blender for a completely smooth texture. Set aside while you assemble the grilled cheese.

  1. Heat a griddle or cast iron pan over medium high heat. 
  2. Butter the outside pieces of bread and pile the grated Gruyere on the inside of one slice. 

Grill one sandwich at a time. For a crispy exterior, sprinkle a little parm on the griddle and place a sandwich on top. After a few minutes peek under the sandwich to see if it’s done – golden brown in color. Flip and cook again on the other side.

Serve the grilled cheese as a side to the soup or cut into squares and pile on top like croutons. Add a sprinkle of reserved sage and a drizzle of olive oil to finish the soup.

Previously on In the Kitchen with Jackie: 


    Hello! My name is Jackie Botto and I’ve been working with Di Bruno Bros. for over five years – styling, photographing and sometimes cooking with all the phenomenal ingredients they offer. CHEESE? Yes, mostly cheese. This blog is the space where I’ll share the things I make. No, I am not a professional chef, I’m a home chef! I cook for myself, my family, my friends – and then I take photos of what I make with the hope it inspires you to cook too.Want to share some tips or pairings of your own? Please leave a comment below!