Heat the oil in a large casserole pot over a medium heat. Add the onion, celery and a pinch of salt and fry for 10 mins, or until softened.
Add the tomatoes, tomato puree, Worcestershire sauce, soft brown sugar and veg stock before covering and allowing to simmer for 10 mins.
Season and blitz the soup with a stick blender until smooth, add in the pasta, cover and simmer again for a further 10-15 mins, stirring regularly to stop the pasta from sticking. Add the milk towards the end of the simmering time.
Spread one side of each bread slice with a thin layer of butter and heat a non-stick large frying pan over a medium-low heat. Place two of the bread slices butter side down in the pan. Split the cheeses between both slices and top with the other bread slices, butter side up. Fry for 3 mins, flip over then weigh the toasties down with a utensil and fry for another 2-3 mins or until the cheese is molten and the toasties are gooey. Slice each toastie into 12 small squares, the size of chunky croutons.
Ladle the hot soup into bowls, season, drizzle over extra virgin olive oil and top with the toastie croutons and a blanket of extra finely grated gruyere.
Notes
A bowl of pure 90’s nostalgia, this tomato hoop soup with grilled cheese croutons might be the after school or work treat, your winter is calling for.