Then I started thinking. Why can't I wear my lolita clothes at work? For the past month, I have started cycling some of my lolita into my work wardrobe, and I have gotten many compliments. I've decided to write up some tips for anyone in a business workplace who wants to introduce lolita into their work wardrobe.
Know your company's dress code
If you work in a legal firm or some other kind of very high-class work environment, the kind that requires a suit jacket every day and prefers pencil skirts or slacks, closed-toed shoes and hose, you probably will not get away with using your lolita items. Unless your wardrobe primarily consists of solid-colored classic-style skirts with a minimum of frills and lace, your lolita is unfortunately going to stay out of your 9-5 environment. Don't risk your job to support your fashion.
Tone down busy prints with simple blouses.
A solid colored blouse, either short-sleeved or long-sleeved, will offset a border print and also make it pop. A blouse with princess seams, puffed sleeves, or muted ruffles will compliment your lolita aesthetic. Avoid blouses with neck ribbons, excessive lace, pintuck bibs or princess sleeves - these details make it look very young, and you want to avoid the doll-like look in a business setting. A good rule of thumb is that the more ruffles and the busier your print on the skirt, the simpler you want the blouse on top. If you don't have a blouse that exactly matches the color of your skirt, you can match it to a color in the print instead - and remember, black and white go with just about anything.
Avoid "cutesy-sweet" prints.
Even if you're the sweetest of sweet lolitas, it's better to save your Milky Planet for weekends and days off. It's a fine line between what's acceptable and what's not - for instance, you could probably get away with Baby's My Favorite Things, even though it has a teddy bear in the print, but something like Merry Sweet Castle is probably too much. People in the lolita community appreciate sweet prints, but in an office environment it will end up looking too kitch. pretty_pastels pointed out that pastel blouses look great with grey or black suit jackets, and it adds a pop of color where there would otherwise be a plain white shirt - yawn! If you're really into pastels, this is probably the route you want to go. It also looks good with a plain black skirt.
Avoid OPs, go for simple JSKs.
As a rule, a full dress looks too schoolgirl and not office. Lolita OPs tend to be covered in charms, lace, beading and ruffles, all of which is going to be too over the top for an office. Go for JSKs instead, like Innocent World's Rose Chiffon - but remember the rule about cutesy-sweet. Innocent World's Lotta JSK is still to sweet for the office, even though it isn't very over-the-top as far as details are concerned.
Say no to OTKs unless it's winter.
It may feel weird to have your legs bare while wearing lolita, but most people in an office environment will give you funny looks if you wear knee-high socks in the summer. Wait until it starts getting cold to bust out your OTKs, and remember to use sock glue to keep them up. Bunched socks that come up under your knees look unprofessional, while OTK socks that vanish into your hemline could pass for tights.
Leave the petticoat at home.
Maneuvering around an office copier and trying to fit under your desk with a frilly petti is hard, and your cupcake sillhouette won't pass for businesslike. If your dress looks sad without some fluff underneath it, consider getting a short petticoat without much volume to it. It'll keep you from knocking the stapler off your desk every time you stand up.
Get a pair of sensible heels - no RHS or tea parties.
Nothing says business like a pair of closed-toed, basic black kitten heels. It can't hurt to own a pair of brown heels, too, for days when black would just look icky with your light-colored outfit. Rocking horse shoes are just impractical in the office - I know many people say they're easy to stand and walk in, but they look like platform shoes, and they aren't really appropriate. Tea parties are once again pushing that line of kitch.
Tone down your accessories, avoid the chunky plastic jewelry in favor of simple gold or pearl jewelry.
This one should go without saying, but I'll say it anyway. Chunky, glittery jewelry is definitely not professional. Stick with simple accessories, limit your bracelets and rings to one or two.
Remove your waist ties, turn your headbow into a ponytail tie.
When you're sitting in an office chair, a big foofy waist bow gets very uncomfortable, very fast. Most skirts and JSKs have removable waist ties, so if you can take them off, you probably should. Slapping a big headbow on the top of your head will make you look a little bit like someone is giving you as a present - pin it onto a hair elastic and pull your hair back in a half-ponytail, though, and it becomes a great matching accessory to your outfit.
Last but not least, if your boss ever looks at you and says, "What in the world are you wearing?" then lolita probably doesn't belong in your office.
Your boss, or your supervisor, has the final say in what you are or aren't allowed to wear in your work environment. Like I said in my first tip, it's not worth losing your job over.
EDIT: Upon request, I uploaded a couple of photos of "office coords." I don't have a real camera, so unfortunately they're cell phone-in-a-mirror pictures and they're a bit fuzzy, but you can get the general idea.
Bodyline's Fairy from Forest Skirt. I paired this with a sheer blouse with a camisole underneath, a simple necklace on a fine gold chain (which you can't see in the picture, sad), and a pearl bracelet. This is an example of pinning the waist bow to the back of my head in a half-ponytail. Another detail that the poor picture quality wiped out is the blouse's texture - it has teeny flocked dots all over it that echo the polka dots in the skirt.
Metamorphose's Blooming Garden Skirt in yellow. On top is a simple, straight-cut long-sleeved pink blouse. I've accessorized with a cameo necklace and left the waist bow pinned to the skirt because the look is otherwise very simple.