Basic Black Dress - The basic black dress has been around for a long time. It is often called the "Little Black Dress", and it's true that shorter skirts on the basic black dress, when they hit you in the right place, can be more flattering than a long black dress.
Trench Coat - The trench coat is one of the pieces that is both classic and currently a hot fashion item. Most any store sells this piece now. It is great for fall and you can pick it up in a wide range of lengths.
Dress Pants - Although it doesn't say black, this is probably what you want to look for. Black is flattering on all figures and goes with everything.
Classic Shirt - The white shirt is a definite classic. But it can also come in many different styles to make it look trendy and not dated or like a man's piece of clothing. Find one that accentuates your best attributes and minimizes trouble spots. For example, if you have wide shoulders, stay away from large collars.
Jeans - Everyone has a pair of jeans, but does everyone have a pair of jeans that make them look great? The wider leg, low-rise jean style has been popular (and still is) but a narrower leg is coming back along with a higher waist, which eliminates the unflattering "muffin top" look.
Any Occasion Top - Find something you look great in that can look respectable under a jacket but bring on the fun after hours.
Skirt - If you need dress pants then you also need a skirt. A skirt is womanly and can be flirty or businesslike. Nowadays women do not wear many skirts or dresses, which makes a lot of them fall into a rut of dressing sloppily or like men. See number 8.
Day Dress - Women also are not wearing as many dresses anymore. It was certainly liberating to go from the '50s when women wore dresses every day to wearing more practical pants for gardening, exercising, and so forth. But the dress does not have to be abandoned altogether. They can be very flattering, and there is nothing wrong with "dressing up" for daytime.
Jacket - A jacket does not have to be masculine. Find one with a proper, fitted shape. Women's jackets should follow the silhouette of a woman's body and accent the hourglass curve at her waist. It is also a perfect piece to put with the skirt or dress pants, and white shirt. Or make it casual with a pair of jeans.
Sweatsuit Alternative - As mentioned before, women wear fewer skirts and dresses these days. But some women have taken casual to the extreme and spend days on end in sweatsuits. It is possible to be casual and comfortable without looking like a slob. Find a comfortable material (that's why this doesn't say jeans again – denim is not as comfortable as a nice soft cotton) that you would want to wear every day. It could be khakis, cords, a cotton dress, or much more.
Bonus: One Indulgent Trendy Item
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