Preheat the oven to 450° F and line a 13x18 inch sheet tray with parchment paper.
Pour 2 Tbsp olive oil, red wine vinegar, garlic and herbs into a gallon size resealable bag.
Add chicken, season with salt and pepper then seal bag and massage mixture over chicken while working to evenly distribute herbs. Set aside and let rest while chopping veggies.
Place sweet potato, Brussels sprouts, apples and shallot on the prepared sheet tray.
Drizzle with remaining 2 Tbsp olive oil then toss to evenly coat, season with salt and pepper to taste. Spread into an even layer.
Set chicken over the veggie layer.
Cook in preheated oven until chicken and veggies are golden brown, about 30 - 35 minutes. Serve warm.