For the creamy winter vegetable soup: Heat the EVOO in a large soup pot or Dutch oven over medium-high heat. Add the garlic, carrots, celery, leeks, parsnips, potatoes, fennel and squash as you chop them and sprinkle with some salt and pepper. Nestle the bay leaves and herb bundle into the vegetables, partially cover and cook until softened, stirring occasionally, 10 minutes. Pour in the wine and reduce until almost evaporated. Then add the stock, bring to a boil and then turn down to a simmer. Meanwhile, melt the butter in a medium saucepan over medium to medium-high heat, and then whisk in the flour 1 minute. Whisk in the milk and season with salt, pepper and nutmeg. Cook until the sauce thickens enough to coat the back of a spoon.
Pour the thickened milk mixture into the simmering vegetable soup, stir to combine and simmer a couple of minutes.
For the cheesy croutons: Preheat the oven to 350 degrees F. Heat the butter and oil in a large skillet over medium to medium-high heat. Stir in the garlic 1 minute, and then add the bread and toast until golden, stirring occasionally. Transfer to baking sheet and dress with the cheese. Bake to set the cheese and further dry out the croutons, 10 to 12 minutes.
Remove the herb bundle and bay leaves from the soup and serve with the croutons.
Cool and store the soup in the refrigerator or freezer for a make-ahead meal. Bring to room temperature before reheating over medium heat. Store the croutons in foil or a cookie tin until ready to use.