Preheat the oven to 450°F (230°C) and prepare a foil-lined baking sheet.
Separate cauliflower into bite-sized florets, slicing larger pieces in half for uniform roasting.
Place florets in a large bowl and toss with olive oil until fully coated.
Sprinkle Old Bay seasoning, chili pepper, and freshly ground black pepper over the cauliflower, tossing to distribute evenly. Repeat seasoning for full coverage.
Arrange the seasoned cauliflower florets in a single layer on the baking sheet, cut sides down if applicable.
Roast the cauliflower on the top oven rack for 15 minutes.
While roasting, grate the sharp white cheddar and parmesan cheeses.
Remove the baking sheet from the oven and evenly sprinkle the grated cheeses over the roasted cauliflower.
Return the baking sheet to the oven and roast for an additional 7 to 10 minutes until the cheese is golden and crisp.
Use a spatula to transfer the cauliflower and crispy cheese to a serving dish and serve immediately.