Heat the olive oil in a heavy-bottomed pot over medium heat. Once hot, add diced onion and carrots. Season generously with salt and pepper. Cook for 5-6 minutes until they begin to soften.

Stir in the garlic, tomato paste, and optional crushed red pepper flakes. Cook for another 1-2 minutes until the mixture is fragrant.

Add the basil, thyme, crushed tomatoes, vegetable broth, and white wine. Bring to a boil, then lower the heat to a gentle simmer. Partially cover and let it simmer for about 15 minutes until veggies are tender.

Carefully transfer the mixture to a stand blender. Blend in batches, filling no more than two-thirds full, and cover the lid with a towel to prevent splatter. Alternatively, use an immersion blender for a quick puree right in the pot.

Return the blended soup to the pot. Stir in your choice of cream or milk and heat over medium-low, adjusting the seasoning to taste.

Ladle the soup into bowls, topping with cracked black pepper, crushed red pepper flakes, and fresh basil leaves. Serve with crusty bread or a grilled cheese sandwich.