There have been two ways that I have gone to handle this issue.
When I first began dressing in lolita I already had some longish hair, primarily due to my prior days as a crossdresser. But for many guys, such a road is impractical. Maintenance or career choice are major obstacles that may prevent a male from wanting or being able to grow out their hair. For those of us unable or unwilling to grow out our hair, there is always the option of a wig.
My current wig collection, minus 2 or 3 wigs not pictured
Wigs of course offer a couple advantages, the first being variety. You are able to style and wear your hair as you want in the time it takes you to put on a wig cap and the wig. I personally do not style my wigs. Having had so little experience styling my own hair before it got cut, I preferred to not practice on wigs that cost a pretty penny. The only things I have done to my wigs are quick bang trimmings to help keep hair out of my eyes *Quite useful for driving, as I found out the hard way when I first began wearing wigs and did not realize how long the bangs really were XD*
In addition, since wigs may not be used every day maintenance is often easier and far less frequent. As you can see from my collection, I have 5 wigs and even though some are used more often than others, I find that I only have to clean some of my wigs every other week and give em a good brushing with detangler after each wearing. *say for example my black and auburn rust wigs, which I find natural and practical. Both are used way more often than the brown hime wig (dislike how if frames my face) or the mint/lavender wig (predominantly for sweet and aiming more for sweet OTT, which I have yet to do*
There are several places to obtain wigs but my personal favorite is
4 of the 5 wigs here are from gothiclolitawigsUSA. I love how soft many of their wigs are and after having met them at Anime Weekend Atlanta, they have super nice staff who explained to me how and why they strive to be the best. Really solidified their position as my go-to wig shop when I want new wigs.
I have also bought from Cyperous wigs
The wigs here are significantly more expensive here but their quality is IMO 2nd to none. Take good care of your wig *something I unfortunately did not do* and the wig will last you for a long time.
Finally, do not forget to take care of your wigs. It would be a shame to spend so much money only to ruin the wigs after only a few uses. Obtain wig heads to let your wigs sit on. Use a brush designed for wigs. Use detangler to make combing out wigs much easier. And get wig shampoo and conditioner to periodically clean wash your wigs. This will help make your wig last and make it worth every penny.
That about covers wigs for me. Tomorrow I will go over the various phases I go through as I perform my transformation.