LOOK AT WHAT YOU HAVE;
Spend some time looking through your existing wardrobe and take stock of what you have. Look over your favourite pieces and remember outfits with them that you loved and that were comfortable. I know some people keep their wardrobes catalogued on Poupeegirl or in notebooks; I keep mine on my Tumblr.
Give your current wardrobe some LOVE! Sell what you don't love any more, fix buttons and put new insoles in your shoes if needed.
Search for outfit photos using the main pieces you own. A quick look through Daily Lolita or Google Images will give you a ideas to try to let you see your existing clothes in a new light.
You can get your inspiration from anywhere; magazines, street snaps, blogs, Tumblr, even just window shopping, but once you've got your idea of what you want, make a note of it!
Make a mood board of your favorite styles and outfits ensure that it's something you can maintain and love for a few more seasons, yet something that can traverse the seasons with different layers.
Where modern wardrobes and fashions can change easily, Lolita and other similar styles are a bit more of an investment so make sure you know what you're aiming for!
FOR EXAMPLE, you can see from my mood board above that although I didn't stick to any colours intentionally, it's mostly pinks, black and creams. Also, there's a lot of frills offset by my punkier/goth roots which I don't want to loose with my Lolita style.
PLAN YOUR JOURNEY THERE;
Think about what you're missing and make a list of what you need, note it in your fashion journal, blog about it, make a wishlist. Whatever your process, get it out there!
Ensure you have enough tops, bottoms and dresses to complete a useable wardrobe. You will have a better idea of what you're likely to need in the long run.
Remember accessories in your 'need to get' list; they are an all-important item in a successful outfit.
Finally, HAVE FUN SHOPPING AND CRAFTING!