In a large pot or a dutch oven, heat olive oil over medium heat.
Add the diced onion to the pot. Sauté until it becomes translucent, around 3-4 minutes.
Add the diced bell pepper and minced garlic to the pot. Continue to sauté for an additional minute or until the garlic is fragrant.
Sprinkle in the chili powder, cumin, smoked paprika, and italian seasoning. Stir for about 30 seconds to allow the spices to release their flavors.
Pour in the canned diced tomatoes. Mix well to ensure the spices don't stick to the bottom of the pot.
Add the drained kidney beans and the diced butternut squash.
Pour in the vegetable broth and add the bay leaf. Stir everything together until well combined.
Raise the heat to bring the mixture to a gentle simmer. Once simmering, reduce the heat to low, cover the pot, and allow the chili to cook for approximately 30 minutes. The chili is ready when the butternut squash is fork-tender.
Season with salt and pepper as desired. Before serving, remember to remove and discard the bay leaf. Ladle the chili into bowls and garnish with your choice of optional toppings.