"That's the beauty of planning", my fashion designer friend assured me. The basic idea is to work around a base colour. It could be any of your favorite colour or the colour you feel flaunts your complexion the best. Ready, it's time to make a kill. Bearing in mind your base colour or neutral colours try and select dresses that can be worn with other dresses also. Ideally opt for a dress/jacket combo. Select a long waist length jacket so that you could easily mix 'n' match it with other dresses. You could also choose lightweight wool or linen jersey or even cardigan sweater as per your lifestyle, comfort and climate.
For very casual lifestyles, a knit T-shirt dress is fine. For a more professional look choose body-skimming princess seams or an a-line shape. Choose designs that are minimal in your solid colours and which can be worn several seasons.
Two piece outfits offer a wide scope for experimentation. For a more formal look you could substitute it with two piece dresses. It could be anything like a naughtily blooming skirt over a bodice flaunting skirt, or a customized skirt and shirt design. But the basic idea is to stick around your base colour and need to be in the same fabric.
For a casual lifestyle, you might choose pull-on jersey pants and a full cut shirt that could be worn either tucked in or left out and unbuttoned as an over skirt. Whatever you choose make sure that it can be worn under the jacket you had earlier purchased with the basic dress. Now go for a two-piece print outfit. Ensure that the print has ample of your base colour as many other of your favorite colours. The design choice is very much up to you, but choose it carefully as it will set the theme of your wardrobe. The dress need not be exactly the same cut as your foundation two-piece outfit, but it should facilitate you to wear them interchanging each other.
Wardrobe reflects your personal style, follow above tips and you can save your money and time.