- 3 tablespoons finely chopped shallot
- 3 tablespoons red-wine vinegar
- 2 teaspoons Dijon mustard
- 1/2 teaspoon sugar
- 1/2 cup plus 3 tablespoons extra-virgin olive oil, divided
- 2 pounds (1/2-inch-thick) boneless chuck blade steaks (sometimes called chicken steaks) or steak tips, gristle trimmed if necessary and meat cut into 2-inch pieces
- 1 pound small tomatoes such as Campari or Baby Roma (about 2 inches wide)
- 3/4 pound okra, trimmed, leaving tops intact
- 16 (12-inch) metal skewers
- Whisk together shallot, vinegar, mustard, sugar, 1 tsp salt, and 3/4 tsp pepper. Add 1/2 cup oil in a slow stream, whisking until emulsified.
- Toss steak with 1/2 tsp salt, then marinate in a sealed bag with 6 Tbsp vinaigrette, chilled, turning bag occasionally, at least 2 hours. Chill remaining vinaigrette.
- Prepare grill for direct-heat cooking over medium-hot charcoal (medium-high heat for gas).
- Meanwhile, toss tomatoes and okra with remaining 3 Tbsp oil and 1/4 tsp salt. Thread tomatoes onto 3 or 4 skewers. Thread okra crosswise onto pairs of parallel skewers, leaving small spaces between pieces. Put on a tray.
- Thread steak onto remaining skewers, leaving small spaces between pieces (discard marinade). Put on another tray.
- Oil grill rack, then grill steak skewers, covered only if using a gas grill, turning once, about 5 minutes total for medium-rare (about 8 minutes if using steak tips). Transfer to a platter. Drizzle with some of remaining vinaigrette while hot and let stand 5 minutes.
- Grill tomato and okra skewers, covered only if using a gas grill, turning occasionally, until tomatoes just begin to wilt and okra is tender, 8 to 10 minutes total. Transfer to platter with steak and serve with any remaining reserved vinaigrette.