Caramelized Brussels sprouts with sweet dates, toasted almonds, and a bright orange-thyme dressing make a festive holiday side that is just as welcome on a weeknight.
Toast the almonds. Arrange a rack in the center of the oven and preheat to 350°F. Spread the almonds on a small baking sheet and bake until golden brown and fragrant, 8 to 10 minutes. Transfer to a plate to cool.
Prepare the Brussels sprouts. Raise the oven temperature to 450°F. Place the halved Brussels sprouts on a large, rimmed baking sheet and drizzle with the olive oil. Season with 3/4 teaspoon salt and a generous amount of freshly ground black pepper. Toss until evenly coated, then spread them in a single layer with the cut sides facing down.
Roast the Brussels sprouts. Roast on the middle rack until browned, 15 minutes. Remove the pan from the oven, add the shallots, and toss to combine. Turn off the oven and return the pan to the middle rack. Continue cooking in the residual heat until the shallots have softened and begun to brown, about 5 minutes.
Make the dressing. While the sprouts roast, combine the apple cider vinegar, orange zest, and thyme in a small bowl. Season with a pinch of salt and black pepper and whisk with a fork.
Combine and serve. Transfer the Brussels sprouts and shallots to a large serving bowl. Add the dates, toasted almonds, and dressing. Toss to combine, taste, and adjust the seasoning before serving.
Prep ahead: Trim and halve the Brussels sprouts and make the dressing. Refrigerate them in separate covered containers overnight. Toast the almonds and store them in a covered container at room temperature. Continue with the recipe the next day.
Roast and reheat: Roast the Brussels sprouts and shallots, then keep them at room temperature on the sheet pan for 2 hours. Reheat in a 300°F oven until warmed through, about 10 minutes. Transfer to a serving dish and toss with the dressing, dates, and almonds just before serving