>>4411294hello-lace, lolita handbook, and F Yeah lolita has some good tips for newbies and veterans. Hello lace also has a HUGE list of shops to choose from (including those with various styles like Anna House, Bodyline, and Taobao shops...out of the Japanese brands, I think that Baby is the most versatile. Innocent world leans towards the sweet/classic look as well).
I would probably write down and cross off a list of things you need for a basic wardrobe:
Blouse, Skirt, Petticoat, bloomers, legwear, shoes, accessories.
Dresses (One pieces or jumper skirts) are probably best for more special occasions.
However, I've found that the best way to achieve a flexible wardrobe is to start with a good petticoat; you need it for every lolita outfit in order to make it lolita. Find a jsk that you love very much. With the jsk, start investing in blouses that will go well with it (long sleeved, short sleeved, black/white - detachable sleeved blouses are great for those on the budget). When you have enough blouses to create several outfits with your dress (and when you get used to wearing lolita), you can start with finding skirts which will go with your choice of blouses.
With that, you can keep checking off your list of other wardrobe basics and accessories that compliment your style/pre-coordinated outfits.