This is going to be a long, picture-heavy post, so be prepared! I compiled a list of things I think are good to know for your first outfit. I am assuming you have already done your research on quality, petticoats, styles, etc. and have a basic understanding of Lolita fashion, but have not actually made your first purchases yet!
When I first started in Lolita fashion, I didn't know any other Lolitas and most Lolita clothing was not available overseas. I had to try with trial and error to find a good coordination, so my first few attempts were quite... special. EGL_Comm_Sales did not exist, so it was more difficult to find second-hand clothing as well!
Luckily, Daily Lolita also did not exist at the time and I did not have a camera so there is little documentation of this embarrassing past ^u^ This post is like a list of things I wish I had known (or had available to me) when I first started in Lolita!
My first outfits were all handmade by me with no patterns. I altered store-bought blouses and sewed the skirts on my own. Now, it is much easier to get clothing from sites such as Bodyline, Fan + Friend, Anna House, taobao, and EGL_Comm_Sales
When choosing your first coordinate, it is best to stick to one of the basic styles (Sweet, Gothic, Classic) rather than trying to do a sub-style (Pirate, Punk, Sailor, Hime, Guro, Ero, etc.), theme Lolita (military, renaissance, nerd/geek, schoolgirl, etc.), or a Lolita + other fashion (Deco, Fairy-kei, Steampunk, Cybergoth, etc.) because you will be able to incorporate more elements into your daily wardrobe and the look will be simpler.
You do not need to buy your clothes from a specifically Lolita shop. In fact, it may be best to start by building your wardrobe with basics that you can wear with clothing other than Lolita to avoid having items that take up room but aren't worn often. Blouses, socks, shoes, accessories, etc. can all be incorporated into your daily wardrobe if you choose more basic styles.
To start with, you are probably most excited about your first Lolita dress! I made a pro and con list for the different types of dress:
It is the easiest to make an outfit from
You don't need a blouse
It is the least versatile
You can change the look with different blouses, boleros, and cardigans.
The top will cover most of your blouse if you are unable to find one with enough frills and fanciness for your liking!
If you have an awesome blouse, most of it will be covered up
It is the most versatile because you can change the top completely
This is the easiest to DIY! (tutorial 1, tutorial 2)
You need to be able to create a good coord on the top separately from the bottom while tying it all together
The segmented cut between top and bottom might not be flattering for all shapes without the right coordination.
Blouse: one in black or white to match your wardrobe. You can alter them or make your own detachable sleeves!
Socks/Tights: in black or white to match your wardrobe (knee-high are most popular, but you can opt for over-knee or ankle socks if you prefer)
Shoes: Mary Jane, ballet flats, or other "cute" style shoes in black (matches the most things) or white (if you can keep them clean!)
Hair: Alice band, ribbon hair ponies, lace scrunchie (tutorial), hair corsage (tutorial 1, tutorial 2), cute hair clips (choose ones you can incorporate into your daily wardrobe)
Accessories: popular motifs include hearts, bows, roses, animals, sweets, etc. and can be found in regular stores
With a print:
No-print dresses that could be commissioned or handmade
*Ruffle blouses in basic black and white are easy to find
*You can alter blouses by adding lace or ruffles to store-bought items
*Simple Mary Jane shoes (with or without heel) can be worn with common clothes as well
*A cute bag to hold your things will stay clean longer in dark colors
*Knee-high socks and/or tights are easy to find in regular stores. Lace sock toppers are easy to make, similar to wrist stoppers (just use more material)!
*Sweet accessories are fairly common. You can find ribbons, roses, sweets, animals, etc.
*I would not suggest to start out with Deco Lolita because it is easy to end up looking like a mess with all the accessories and wigs or hairpieces if you are inexperienced!
*If you have an all-over print dress, it is better to wear a solid blouse
*If you are already Goth, you probably have awesome shoes to wear with your coord!
*You can choose how to balance your look with Goth-cute, Creepy-cute, or Elegant Goth depending on your accessories
*Like Western Goth, common motifs include crosses, roses, bats, bones, and eyes (for creepy-cute look)
*Dusty/muted jewel tones are common
*Floral print fabric is easy to find and frequently used
*Classic Lolita is more elegant and may be easier to wear in public
*This style is very fitting for the Victorian and "granny" style booties, which are so cute!
*Floral corsages are very lovely and elegant
*High-neck blouses are more common than Peter Pan collar blouses - good for wearing cameos and brooches!
*Most Classic Lolita dresses are A-line, so you will need an A-line petticoat rather than a bell-shaped one!
I hope this list was somewhat helpful. If you have any suggestions, tips, or questions to add, feel free to drop a comment or email and I will respond quickly!