Finely hand-chop the parsley, oregano, and garlic — do not blend, as hand-chopping gives the best texture and color. Combine in a medium bowl.
Add the red wine vinegar, olive oil, red pepper flakes, salt, and black pepper. Stir well to combine. Taste and adjust seasoning. Add 1-2 tablespoons of water if you prefer a thinner consistency.
Let the chimichurri rest at room temperature for at least 15-30 minutes before serving. This is essential — the flavors need time to meld and mellow.
Prepare and Cook the Steak
Remove the steak from the refrigerator at least 30 minutes before cooking to bring it to room temperature. Pat completely dry on all sides with paper towels — a dry surface creates a better crust.
Season generously on both sides with kosher salt, black pepper, and garlic powder if using. Press the seasoning in with your hands.
Heat a cast iron skillet or grill over high heat until screaming hot — you want to see the oil just begin to smoke before adding the steak. Add the olive oil.
For skirt or flank steak: cook 3-4 minutes per side for medium-rare, or until internal temperature reads 130-135°F on a meat thermometer. Do not move the steak once it hits the pan — let the crust develop undisturbed.
Transfer the steak to a cutting board and tent loosely with foil. Rest for at least 7 minutes — this is non-negotiable for a juicy result.
Slice the steak thinly against the grain — this is critical for skirt and flank steak, as cutting with the grain will result in chewy, tough bites.
Arrange slices on a platter or board and spoon chimichurri generously over the top. Serve immediately with extra chimichurri on the side.
Notes
Make-ahead tip: Chimichurri can be made up to 24 hours ahead and stored in the fridge. Bring to room temperature before serving. Storage: Store steak and chimichurri separately in airtight containers in the refrigerator for up to 3 days. Reheat steak gently in a skillet over medium-low heat — do not microwave. Slicing tip: Always slice skirt and flank steak against the grain for tender results. Look at the direction the muscle fibers run and cut perpendicular to them. Grilling option: This recipe works beautifully on an outdoor grill. Cook over direct high heat for the same timing, and get those grill marks in by not moving the steak until it naturally releases from the grates.