This post is meant to help guide people who are starting to dip their toes into lolita fashion. I've covered the things that I'm qualified to write about; I've included links to other useful posts that talk about things that I haven't written about here.
Another thing to remember is that there are no steadfast "rules" to lolita. It can be difficult to sort out what is and isn't lolita. So don't worry about getting every detail right, especially when you're starting out.
On to the tips!
- One thing I'm going to say right off the bat: your shoes don't have to be the same color as the rest of the outfit. I'd recommend getting a good pair of black (or brown) mary janes. Unless you're doing shiro (all-white) or something, it's perfectly fine to wear black shoes. So if (say) you wear a pink jumperskirt with a white blouse & socks, black shoes will still look good. (The reason I'm emphasizing this is that I've noticed that some people get worried that they have to have pink shoes to wear a pink dress, etc.) (There are some dresses/skirts (usually classic ones) that look better with brown than with black, so if you have such a dress/skirt, then you might want to get some brown shoes.)
- For getting brand pieces I highly recommend the lolita sales community on LiveJournal. You can get a wide variety of loli clothes there second-hand. It's cheaper than buying new, and you don't have to use a shopping service.
- As for blouses, I'm a fan of Anna House. Their blouses are sturdy and can be hand-washed cold. (The tag says "dry clean only", but in my experience hand-washing is fine. Just don't iron/put the blouse in hot water, as the rayon lace will melt.)
- Don't fret over getting brand socks. I wear lolita most of the time, and I don't own a single pair. Socks are easy to get off-brand, even in the socks section of whatever clothing store you shop at. I'd recommend starting off with white knee-highs (or over-the-knee, or even tights). You can add other colors (and find some printed ones) later. (I wear a lot of black, for instance, so I have a lot of black socks as well as white; again, they're not all printed.) Printed socks can also be found pretty easily. If you can't find them at a local store, there are places online that carry loli-esque socks. Most of them don't even advertise them as lolita.
- An odd thing I've noticed is that some beginner lolitas are worried about the necessity of bangs. I'm not sure how the confusion arose, but let me assure you that bangs are not required for lolita.
- Anyway, hair styles in lolita range from very simple to complicated updos. Some simple styles include braids, a headband/headbow, a hat, pigtails, and a nice hair clip or two.
- I'd say that most (if not all) complicated lolita styles involve curling your hair. Now, there are many ways to do this, and different people have different ways of doing it. You can use a curling iron, hot curlers, sponge curlers, rag curls.... Different methods work for different people. My hair doesn't hold a curl with an iron, but sponge curlers work like magic for me. (Protip: wash your hair before putting in sponge curlers, so it's clean and wet.)
- Pigtails and rectangular headdresses both look great with curls, and imho pretty much any hairstyle looks good with them. One fancy updo I particularly like for special occasions is this Regency-inspired one. (Protip: curling your hair overnight works, so it's okay if you do that instead of overnight braids like in the tutorial. Also, it looks just as good without a ribbon.)
- I don't wear wigs myself, but this post on the blog Parfaitdoll is worth reading.
- Try matching your socks with your blouse. That is, wear a white blouse with white socks. I think it helps to tie the outfit together. Also, match the main color of you "main piece" (the skirt, JSK, or OP) with whatever you've got in your hair.
- You don't have to match prints to the letter. If you have a black skirt with white roses on it (or something), then a solid black beret or headbow is fine. A slightly-different print is also fine. So, if you have a printed main piece, don't worry about getting the matching headbow.
- Don't worry about having everything be the exact same shade of ___. If your pink bonnet is slightly lighter than your pink dress, that's completely fine. Don't worry about exact matches. Some shades are lighter, darker, dustier, etc., than others. This goes for all colors -- even blacks and whites can vary a bit, and that's perfectly okay.
Finally, I'm going to recommend a couple of useful links:
How to Have Your Dream Lolita Wardrobe -- This is a great article from a well-respected lolita blogger.
How to Wear Lolita Everyday- The Everyday Lolita -- This is more geared toward people who want to don the frills a lot, but it's still worth looking into, even if you just plan on wearing lolita for special occasions, imho.
Universal Currency Converter -- This is very useful when you're buying things in a currency other than your own.