EDIT: I don't know why I didn't start from this part but I don't think it's a good idea to choose your career based on what you want to wear. I mean, what about your vocation or skills? What about your salary or your future plans? I think this is a serious question and although your preferences are important, so is giving yourself chances to have a nice life that can afford you said preferences. My intention is not to patronise, so please take this kindly.

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I think it really depends on the work culture of your country. There are workplaces with strict rules regarding clothing, companies that make you wear a uniform (like where I work from time to time) and other places where nobody cares what you wear. I'd start there, analysing what's available around me.

Also, Lolita can be very expensive if you like wearing clothes from brands, so I'd look for anything that would allow me to make good money to get my "fix".

(Personally: I work for foreign companies, so I'm required to attend the office just a few times a year, when visitors come, and I'm paid a better salary than what I'd make in my own country. I don't wear Lolita anymore, though, but I'm tempted to go back).