So you want gorgeous tresses of your own, but need to keep a masculine appearance for work or social reasons? Wigs just not cutting it for you? Don’t worry, there are plenty of ways to feminize your hairdo!
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Ok, first step though . . . you do have to grow out your hair a little. You don’t need a ponytail, and you don’t have to tell your barber that you want a “girl cut” – a medium length guy’s cut will work just fine. If you don’t believe me about the medium length mens haircut, this is me as a guy. I’m in the process of growing my hair out a bit longer and trying to figure out what to do with it, but the current length and style of my hair is pretty close to this photo. Sure doesn’t look very femme, does it? You’re probably thinking I have to wear a wig all the time, but not true! I have plenty of options with my hair like this
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I’ve always had a thing for pigtails, so this is the first thing I learned to do to feminize my hair. Sure, they’re nubby little pigtails at this hair length, but they still give a decidedly feminine look – especially with pink hairties! Because guys haircuts tend to be much shorter in the front than girls haircuts, you probably won’t be able to get all the hair on in the front pulled back into the pigtails . . . which is where the headband comes in. On the upside, most guys haircuts will make for some great bangs, which will make you look young and adorable when crossdressing

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Ok, so that’s the first femme hair style that most crossdressers try. And as much fun as pigtails are . . . it’s probably not the most feminine look you can achieve with relatively short hair. Don’t get me wrong, I love pigtails and am working on growing out my hair long enough that I can get some decent ones (without losing my day job!). There are just some other styles that work better with shorter hair.

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Here’s a style I just figured out today completely by accident. I have a natural center part, and I couldn’t figure out how to get my bangs to look the way I wanted (center parted bangs look ridiculous :p ). So I decided to part my hair on the side, and as I played with it I started to notice that I could straighten out my curls and get a great wave of bangs that almost cover my one eye . . . a very sexy sassy look. That was the easy part though – I still looked like a guy with a crazy combover if I stopped there. The secret to turn this into a femme hairdo is to comb the sides of your hair straight down over your ears. Most guys (and many girls) tuck extra hair behind their ears to keep it out of the way, but you can get a great flipped out bob look by just combing your medium-length guy hair straight down over your ears rather than tucking it back! Sweet

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Alright, if short hair just doesn’t do it for your femme side, but you want a secure natural look . . . extensions can be a great option. This photo is my natural hair with a single comb-clip extension – the cheap and easy way to get long hair I think this clip cost me $15. The most important part is that you have to match the hair type and color of the extension to your natural color. Dark browns like mine are of course pretty easy to match, but finding an extension with enough curl was really difficult. Well, until I found this one.

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A word of warning though, a single comb like this will typically only work for a down-do. If you try to put it into a ponytail, pigtails, or anything else its attachment point will become very obvious. Multi-piece extensions will work much better for styling, but are typically more expensive and more work. And personally, my multi-piece extensions just look way too thin in my thick curly hair – I’d need 100 pieces to make it work! On well, such is the life of a crossdresser

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Hope you found these crossdressing hair style tips useful. I’m always looking for new things to do with my hair, and I’m certainly not an expert yet . . . so if you have any other ideas I’d really love to hear about them! Actually, I will probably be getting my hair trimmed up this weekend – any ideas what I should ask my barber for?

Most crossdressers require a wig. Only the very fortunate of us can afford to keep our hair long . . . and even then there is the threat of a job interview or new significant other, etc that would necessitate chopping off those gorgeous locks. So before that day comes, you might as well be prepared with a wig. And who knows, you might find that the wig suits you better than your own hair!
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Once upon a time I had long hair myself. And I will tell you, the one thing a wig can never replace is the confident secure feel of your own hair. But a wig can let you change your hair length or color whenever your heart desires. I think those are the primary tradeoffs.
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Ok, so if you’re looking into a wig at this point there are two things to consider: natural or synthetic, and full wig or extensions. If you have moderately long hair, you might want to look into extensions. You can find clip in extensions made of natural hair that will look incredibly realistic for cheap. They take a bit more skill to apply, and they can be a bit awkward to style in some cases (especially if you want pigtails or something of the sort). Generally speaking they work best for straight hair, and if you have a lot of volume in your natural hair they will look a bit stringy and thin. So let’s assume for the moment that you’ve decided to go with a full wig. More on extensions some other time.
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Natural hair wigs provide the ultimate in realistic look and feel and can be styled to your heart’s content. They last longer than synthetic wigs, and will not get split and frazzled at the ends nearly as much. That said, natural hair also requires a lot more care and is ~10x as expensive. If you’re going to buy a natural hair wig, expect to invest some time keeping it nice (just like you would your own hair), expect to go to a salon to have it styled the first time (they usually do not come pre-cut and styled), and expect to own only one. Natural hair wigs typically cost several hundred dollars or more.
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A comparable synthetic wig can be picked up for $30-$100 (just don’t buy cheap costume wigs as they never look realistic and the fibers break quickly) and will last you several years if you treat it well. If you use and abuse it (like I do for my website), or wear it frequently (daily), plan on replacing it every year. Even with yearly replacement though, synthetic wigs will work out to be cheaper than a natural hair wig. Don’t get a synthetic expecting it to last forever though – synthetic hair pieces wear out, especially with aggressive brushing or styling. Synthetic wigs also come pre-styled . . . which can be both a blessing and a curse. You don’t have to worry about cutting them or going to a salon (you can wear a synthetic hair piece “out of the box”), but if you try to style it too much you will likely be frustrated – synthetic fibers are stiffer than natural hair and start to look like plastic (that’s what they’re made of afterall) if you pull them too far out of their preferred alignment.
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All said, I would start with a synthetic wig. Try it out, wear it a few times. Remember that you can afford to buy a few of them for the price of a natural hair wig. And if at the end of the day you decide that you really need that extra realism, then go for the natural hair . . . just make sure you know what style you want before you shell out that kind of cash!