Starting from head to toe for the most part. A lot of this advice does not apply to aristo or boystyle though I may add some stuff later, and often punk has a lot of exceptions. For more on the different styles, see here. I apologize that most of the pictures are of sweet lolita BTSSB, but they have the most variety on their site. Click on the little pink hearts in the descriptions for examples.
There are many different types of hair accessories to help pull your outfit together. The most obvious is the headdress ♥, which is either a round or rectangular piece that is decorated with lace and bows that ties around your head with a ribbon. This is worn best with bangs but beware that no matter what hairstyle you have it can easily look like a maid's. A less maidish and more casual but still very lolita hair accessory is the hair bow ♥, which can attach either by clips, a hair comb, or a headband (such as Alice bows ♥). If you don't want such a large bow you can also opt for mini bow-clips ♥. Old-fashioned hats and minihats are also common styles but are harder to make at home. Tophats and mini-tophats are often found with punk and boystyle, but some of the more feminine hats ♥ are suitable for any style. Mini-crowns ♥ and tiaras ♥ are a must for himeloli and can also look very good with punk styles. Mini-straw hats ♥ go perfectly with country style and are usually decorated with ribbons as well as small fruits such as cherries or strawberries. Possibly the hardest hair accessory to pull off is the bonnet ♥ which can easily look too childish. Look for a bonnet without an overly wide or floppy brim and never tuck your hair fully underneath. Some less common but still elegant hair accessories include berets ♥, caps ♥, rose clips ♥, hairbands ♥, and cute earmuffs.
♥Jewlery and other accessories♥
Lolita jewelry is hard to define because almost anything can coordinate with a lolita outfit - especially oldfashioned jewelry or jewelry with loli motifs. Lockets, cameos, pearls ♥, and loli-esque charms ♥ (keys, bows, hearts, cakes) fit very well. Chokers ♥ are good for gothic, punk, and ero-loli styles. Ties ♥ can fit with almost any style, but not just any old tie will do. Lolita ties tend to be shorter and fatter, often coordinating with a skirt and decorated with lace or even appliques. Neck corsets are fit with these styles, but these can look awkward if they are too big or your neck isn't long enough. You can also have matching wrist corsets or the more lolita wrists cuffs ♥ - which are like stocking toppers but are worn on your wrist. Gloves can be worn as well, but make sure they suit the outfit. Long gloves ♥ tend to fit best with aristo or classical styles, while short gloves ♥ are sweeter in nature and suit himeloli especially well. The key to coordinating these accessories is to keep them elegant, feminine, and not-cheap-looking.
Some more seasonal accessories are scarves ♥, mittens ♥, and muffs. Scarves, mittens, and muffs should be cute, elegant, and coordinate well with your outfit both otherwise nothing short of bunny scarves are very lolita-specific. Look for ones that match well with your winter coat.
Lolita jackets can be divided into two major classes by weight. Light jackets ♥ are worn to coordinate with a skirt and can be worn during any season so long as you don't feel too warm. They are similar to suit jackets but they have more feminine collars and rounded edges. Some even have puffed sleeves, but the key is the softer shape and the frilly trim.
Heavier coats ♥ are for winter (obviously). Like old-fashioned coats, they are designed to fit voluminous skirts underneath, so they flare a bit at the bottom making them look a bit like dresses themselves. They are much longer and more fitted than a lot of modern coats (no short puffy jackets). A number of these coats also have attached capelets (as seen in the example), which can either be made out of the same wool as the coat or be lined with fur. You can sometimes remove the fur collars from coats if you want a less fluffy look. Some coats also have hoods, and some come with cute animal ears - especially bears and bunnies. These can be very expensive so find one that goes with everything.
Capelets ♥ are essenitally small, elegant capes. Those that are are made of cotton and only cover your shoulders aren't very good for keeping you warm, but they are still somewhat seasonal because they should be worn over a long sleeved blouse. Capelets like this aren't really meant to be functional and simply coordinate with your skirt or dress. Longer capelets ♥ (which could probably be called capes at this point) made of wool or velvet are better for keeping warm in the winter months and look especially cute with muffs. Winter capelets can come with hoods much like those of the lolita coats.
Boleros ♥ are the cute little shrug-like sweaters that tie in the front that brands like BTSSB put out. Often they are knitted, but they can be made of any fabric. But they always look very delicate with little ruffles or puffed sleeves - they don't keep you very warm but they can keep out a Spring chill.
Cardigans ♥ are a little more casual but they are good for keeping you warm in only slightly chilly weather and for coordinating with your skirt. A lot of cute cardigans will go with your lolita clothes, but those that are strictly lolita have a very feminine cut that's not too fitten and are typically trimmed with ruffles or a bow. Some may have a lolita print or applique such as a crown.
When looking for a lolita blouse look for something very feminine and a bit old-fashioned. It's not just lace and ruffles that make a blouse lolita - it's also the shape. Pointed collars can work, but a rounded ♥ or high collar ♥ are more fitting. The same applies to sleeves - straight sleeves can work, but puffed sleeves or sleeves that are gathered at the end are preferable. It should be tailored for the female shape but not overly tight. The fabric should be crisp (not the wrinkly stuff) and should never be see-though. Overall it should look a bit formal and elegant while still being very soft and girley. Avoid more typically masculine features like hardware (buckles, etc.) and large pockets.
Cutsews are perfect ♥ for a more casual loli style (though many cutsews can be worn even for formal lolita style). What makes something a cutsew is they are typically make out of knit fabrics so they can simply be cut and sewn, without all the tailoring needed for blouses or other cotton clothing. They aren't simply t-shirts (though a few of the brands have put out very loli baby tee with cute prints), they are trimmed just like a blouse or a cardigan ♥ with ruffles, lace, or puffed sleeves. They can have collars or have a tshirt-like neckline, occasionally trimmed with criss-criss straps that tie around your neck. They are a more comfy alternative to blouses or heavy jackets.
♥Bags and parasols♥
Bags ♥ and Purses ♥ are one of the last things people think about when coordinating a lolita outfit, but they really do bring an outfit together. There's tons of purses out there that perfectly match a single outfit down the the lace, bows, and the little bunny applique, but all that really required is something pretty and elegant that goes with your general color scheme. Lolita purses are very adorable, sometimes they are shaped like hearts or outer lolita motifs, other times they are shaped like everyday purses but trimmed with bows and lace. They are made of good material, they aren't floppy and they shouldn't show signs of wear. Bags or totes are typically bigger and floppier, but they are still cute and elegant - they are made of nice fabrics, sometimes patterned, and will often have a lolita print on them such as a scene from Alice in Wonderland.
Parasols ♥ can easily be distinguished as very lolita by their frills and old-fashioned appearance. They are not simply umbrellas with lace sewn on - they are far more delicate and usually more attractive. Children's umbrellas can sometimes work but look for one with a curved or otherwise elegant handle that extends rather than pops out (umbrellas that fold back in on themselves don't usually work). Asian style parasols are typically only suitable for waloli and should not be used with other styles.
Skirts ♥ are the cornerstone of lolita clothing. Their bellshape provides the typical lolita silhouette, and their length (for anything but ero) is typically around 2 inches above the knee. They should sit at your natual waist (not where you wear your low-rise jeans but right around your belly-button). Trimmed with the typical lolita arsenal - lace, ruffles, ribbons, bows, appliques - it's not hard to figure out what skirts are lolita and which aren't. Note: not all lolita skirts are bellshaped but those are hard to pull of right so beginners should stick with this general rule. Some skirts are tiered ♥, some have scalloped edges ♥, and some have cutouts to display an underskirt - there are too many possibilities for skirts, one-pieces, and jsks so I'm just going to provide some examples rather than trying to explain.
One-pieces ♥ are dresses that can be worn by themselves or sometimes with a blouse underneath. The bodices have a lot in common with cutsews - they can have puffed sleeves or cross-ties or lace trim. The skirts resemble typical lolita skirts, though they may be elongated if the dress has an empire-waist. Again, too many possibilities, so here are some examples.
Like one-pieces but without the sleeves, jumperskirts ♥ are made to be worn over a blouse but can be worn on their own in warm enough weather. Plenty of examples to choose from.
♥Waloli and Qiloli♥
Waloli outfits ♥ are inspired by Japanese clothing. They aren't simply kimonos that are cut off with a poofy skirt underneath - care is taken to trim the kimono like any other lolita piece or the obi might be made into a cute bow. Sometimes all that is need to make something waloli is a Japanese print fabric on a dress. Qilolita ♥, inspired by Chinese clothing, is equally more elegant than just a qipao over a flooofy skirt. First of all, the skirt needs to match the print of the fabric, second the shirt or dress must be cut appropriately to accommodate a large skirt underneath. These are not very common styles and they are often done wrong, so it may be better to find your footing in the usual lolita styles before attempting waloli or qiloli.
Aprons aren't just for Alice in Wonderland costumes or french maids anymore, but they still have a bit of a custumey feel so only wear during appropriate situations (such as while cooking) or if you feel confident you can pull it off without it looking like a costume. There are two main types of lolita aprons, those that cover your entire front ♥ and those that only cover the skirt ♥. The full aprons can sometimes have shapes at the bodice such as hearts ♥, bunnies, or gloomy bears, and both they and the short aprons are trimmed like any other lolita pieces.
What gives the lolita skirt it's telltale poof is typically a petticoat ♥, a bell-shaped but lightweight fluffy skirt-like garment you can wear under any skirt or dress. Do not use a square dance petticoat. Go for a high-quality pettiocat with enough fluff that won't show through your skirt. Short bloomers ♥ can help give a skirt some poof and are also good if you plan to run around in your lolita clothes so people won't be getting any panty shots.
A bloomers FAQ by Ugly_kitties
I don't want to spend too much time on corsets, but I do want to say please be careful. If you want to wear them under clothing, that's fine, just don't lace them too tight. I know they cinch your waist but all that extra weight has to go somewhere and it's usually shoved upwards, making your look like a linebacker. Little girls don't have extreme hourglass shapes, so save the tight-lacing for aristo styles, and go for a more comfortable shape with lolita. If you want to wear corsets on top of your clothes, that can be fine as well, so long as it coordinates with your outfit (please don't wear a black vinyl corset with a pink outfit) and doesn't push the fabric or your body around into weird shapes. Also, a note for underbust corsets - wear a good bra, a, avalanche of boobs flopping over your corset is so not lolita.
Lolita stockings aren't exactly underthings, but they're going in this category any way. Stockings should be *knee-highs* or full on tights unless you're going for ero loli. Thigh-high stockings won't fit under a knee-length skirt (unless you're trying to give the appearance that they're full tights which is fine) and short little socks look like sissy style (something you probably don't want to be associated with). With that said, stockings can be worn two different ways. One is simple the stockings themselves ♥ - these stockings generally have cute patterns or decorations (such as ribbons lacing up them) that make them lolita on their own. Sometimes you can find striped stockings - not the gaudy goth-style of hot topic stockings, but knee-high ones made with knit material that are elegant in their own way. These look best when worn in pastel shades ♥ rather than black and white. But often they are worn with stocking toppers ♥ - just a bit of lace and ribbon that goes at the top of the stocking to match the frill of the rest of your outfit. Sometimes they are attached to the stockings but they can come separately with elastic inside so they can be worn over any stocking.
The basic lolita shoe is the mary jane ♥. These can be trickier to find for adults but look for one in which the strap goes over the top of your foot nearer to you shin than to your toes. Flat, platformed, and high heeled mary janes are all good choices, but avoid mary jane-esque shoes excessively high heels and a strap around the ankle (commonly referred to as stripper or drag queen heels). Ballerina flats ♥ (like mary janes but without the strap) tend to look slightly less youthful and coordinate better if decorated with bows or lacing. Another common lolita shoes is the rockinghorse shoe ♥, originally designed by Vivienne Westwood but now you can find several brands that carry then (see "where to buy - shoes"). Boots ♥ are sometimes harder to fit into lolita style (with the exception of punk), but several of the major brands have come out with very cute boots. It is also possible to work in cute sandals ♥ with your summer lolita attire. Traditional Japanese wooden shoes or Chinese slipper shoes work for waloli or qiloli, respectively. For punk lolita there are a lot more options (including clunky boots and even converse) as long as the rest of your outfit is very lolita.
For more on the materials used in lolita clothing, see here.