Measure the vinegar, honey, garlic powder, mustard, oregano, chile flakes, salt, pepper and 1/3 cup of oil into a jar with a tight-fitting lid. Shake until combined.
Pour ¼ cup into a smaller jar, add the 2 Tbsp. of oil, cover and refrigerate for the salad dressing. Makes about 1/3 cup.
Pour the remaining dressing into a zip top plastic bag, add the steak and mix to combine. Refrigerate 2 hours or overnight.
Pat the steak dry and grill/cook to your desired level of doneness. Let rest 15 minutes, then slice thinly against the grain. Dress salad greens/arugula with a few tbsp. of the reserved dressing. Top with sliced steak, shaved Parmesan and a drizzle of the dressing.
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BOLD BOOST TIP: Pouring ½ cup of Holland House® Red Cooking Wine into your favorite chili recipe gives you an easy addition of robust flavor.