Cut stems off Broccoli (1.5 pound) cutting very close to the flowerettes. Separate flowerettes into small pieces. Set aside 3 cups of flowerettes.
Using a vegetable peeler, lightly peel the thick skin from the thicker stem pieces, discard skin. Chop stems, along with any remaining flowerettes into 1/2" chunks.
In a medium pot, heat Unsalted Butter (3 tablespoon) over medium heat until foamy. Add Shallot (2) and Garlic (1 clove), cook until soft, about 5 minutes, stirring occasionally.
Add chopped broccoli, Chicken Broth (3 cup) and Fresh Oregano (1 tablespoon). Bring to a simmer, cover and cook until very tender, 15-20 minutes.
Stir in Potato Flakes (1/2 cup) and Dijon Mustard (2 tablespoon). Allow to cool for 5 minutes, stirring occasionally.
Using a blender or submersion blender, blend soup until smooth.
Return to pot, add 1% Low Fat Milk (1 cup) and broccoli flowerettes. Bring to a gentle simmer and cook covered until flowerettes are tender, about 10-12 minutes, stirring occasionally.
Remove from heat and season with Kosher Salt (1/4 teaspoon) and Ground White Pepper (1/8 teaspoon). Adjust thickness with more broth if needed. Stir in Cheddar Cheese (1 cup).
Serve immediately garnished with additional cheese, if desired.