White Button Up Blouse - can be worn with jeans or a skirt. Add a necklace or a scarf and you're set.
Motorcycle Jacket - I wear my leather moto jacket with jeans and with my skirts and dresses. If a biker jacket isn't you, choose a more simple leather or faux leather jacket. If you select a style with few embellishments and a flattering shape, it will last for years.
Cashmere Tee - I wear my lightweight cashmere tee alone and layered with a shirt. I throw it on with jeans on the weekend and with a skirt for work. The lightweight cashmere is warm but not too hot for layering.
Simple Women's Cut T-shirt - A simple t-shirt is so versatile. A women's cut is more flattering for women (petite to plus) and isn't boxy. I love my gray t-shirts. I have quite a few but any other neutral would do (white, black, ivory, tan). I usually snag mine at Old Navy or Target. I think paying a ton for a t-shirt is crazy.
Black A-Line Dress - Most lists say that you should buy a black sheath dress. I disagree. An a-line dress is flattering on all body types and it's more forgiving when you gain or lose a few pounds. If the fit is good you won't even need Spanx (bonus). I'm a pear shape (I'm sure you've noticed) and an a-line dress looks better on my shape than a sheath. My sister is tall and lean and proportional. She looks great in both.
Black Ankle Boots - They go with everything! Pants, skirts, dresses, casual or a bit dressy. I wear mine constantly. They work for more than half the year.
"Nude" Flats (or Heels) - I have both nude flats and nude heels. If you want something in between, go for a mid or kitten heel. They elongate your legs and will work with every outfit you own. Remember, nude is not universal. You'll want to try on your "nude" flats or pumps to make sure they work with your skin tone. My friends with darker skin tones will want to gravitate toward a tan or brown shoe.
Jeans (Dark Wash) - A great fitting pair of jeans (skinny or straight leg) can be dressed up or down depending on the day. I own both skinny and straight leg jeans. There are lots of brands and they all have a different fit. I love NYDJ jeans. They work for my pear shape and come in tons of styles and colors. You can always find them on sale for great prices at places like Nordstrom Rack, 6pm.com, and Amazon.com.
I'll expand on styling these basics over the next few weeks.