When I think of classic style, the first celeb I think of is Jennifer Aniston. She seems to add a little flair to her outfits with fun accessories, so maybe that's a good solution.classic wardrobe pieces with fun jewelry, scarves, belts and shoes.
Country Concert Outfit: Turquoise dress with jean jacket and sandals. Could substitute the sandals for your cowboy boots for fall/winter country concert. Maybe not the jean jacket. DO they have nay outfits without the jean jacket on the dress?