Essentials

• That little black dress. (but not too little!) Still talking classy here.
• Trench-coat. Nothing beats having that sash to pull taut. Or you can opt for a pea-coat (I have both :) Make sure your coat is a fairly neutral color.
• At least one pair of heels. Make 'em red, and you can pop any monochromatic outfit.
• A stylish full suit, preferably one that can be worn year round.
• Sundress. This can actually be worn year-round, just pair it with jeans!
• Skirts are an absolute must when trying to be as classy as say Jackie O.
• Pearls! Real or fake. Long or short. Pink or white.
• A fashionable good sized purse for everything that you carry around.
• Headband, scarf or hat. Not everyone can pull off a hat, but you should do something with your hair.
• Button-up shirt. At least one white crisp shirt...need to find one yet...oops!
• Boots. Cowboy boots, snow boots, knee-high boots...oh the possibilities! (but no Ugg's!)
• Leggings. WARNING: not to be substituted for pants. Use these when its just too chilly to wear just a skirt or dress, or you just want to add some color.

...and this list could go on. Try to get as much as you can, and just keep building. I don't have everything yet, and I'm writing this post

:-)