Below are three evening looks using your twenty autumn/winter clothing items and accessories. For these looks, I have provided two alternatives--one for women my age and another for women a tad older.
Evening Look No. 1
This outfit is perfect for a dinner date with your special someone. Both outfits pictured above feature your age-appropriate going out top. For the older look (pictured second), place your blazer over your going out top, button it, and cinch it at your waist with your skinny belt for an extra-polished look.
Evening Look No. 2
This evening look is great for a cocktail party. The only difference between the younger version pictured first and the older version pictured second is the choice of shoe, with the older version substituting your pumps for your boots, for a more classic look.
Evening Look No. 3
This outfit is the most casual of all of the evening looks and is best suited for a night out on the town! The younger version pictured on the left incorporates your tall boots -- go ahead and tuck those jeans into your boots for a more funky look. The older version pictured on the right swaps out your tall boots for your pumps and features your age-appropriate going out top.