Feminization 101: Crossdressing Men

Trying to make a male look like they’re female? It’s both easier and harder than you think. Ironically, women are often the worst at feminizing men for reasons I’ll go into shortly. However, it is possible to achieve dramatic results with a slightly different approach. If you want to transform yourself, or want to help someone dress up without looking awful, here are some helpful tips.

When artists first learn to draw, they’re taught to draw the spaces around things, rather than the things themselves. This idea of ‘negative space’ stops them from drawing what they believe an object looks like, and instead helps them focus on the actual details in front of them. We have a really powerful mental model of how the world looks, which isn’t really accurate but emphasises the things our weird brains think are important. That’s why cartoons can be physically impossible but instinctively ‘look right’.

What does this have to do with cross dressing?

Well, firstly, no, you’re not going to end up looking like this. No-one looks like this, not even with Photoshop.

Secondly, successful transformation is about understanding the ‘negative space’ between a male figure and a female one. It’s tempting and instinctive to reach for the clothes, styling and makeup that make a woman look attractive, but often this will make a guy look like… a badly dressed guy. Instead, you’ve got to work with what you’ve got, which needs an entirely different approach.

That’s the reason women can end up approaching feminization believing their lifetime’s worth of experience has taught them how to transform into Cinderella — but instead turn their unfortunate victim into an Ugly Sister. Sure, that’s great for a hilarious Halloween costume, but we know it’s possible to do better. At this point, we’ll have to send in the boys… well, the drag queens at least.

Hold on though, there are some basics that you’ve got to get right before squeezing into those sequinned slippers.

It’s no good spending a fortune on a whole new look, if you’ve not done the groundwork. At the very least, good grooming makes a world of difference regardless of your gender, so trim those bushy eyebrows, get that hair cut, clip and clean those mucky nails and have a good wash. It doesn’t matter if the plan is to crossdress once, or to stay en-femme forever — getting into a good grooming routine will move your appearance up a level. Here, the emphasis should be on neatening up those edges and improving skin tone, rather than the typical male approach of hacking at it until you’re sore.

Of course the most obvious male attribute is body hair, and here are some choices to be made. Shaving your face properly is fairly uncontroversial (though remember to moisturise, not splash on harsh alcohol based aftershave). Regular shaving will improve matters, but for those with dark hair, beard shadow may still be a problem — that can be dealt with with a bit of makeup knowledge.

Removing the hair on your body might be more of a challenge, especially if this is not something you want to make public. This can be solved with clothes that cover, but wearing a full body sack might not be that attractive.

Since we’re not uniformly hairy, it can be possible to give the illusion of more exposure by picking good areas to show off, like the Bardot top on the left.

On the other hand, if the only aim is to get a cool photo or look convincing in passing, light hair can be disguised by texture (it’s amazing what fishnet can do!). Unfortunately, this won’t survive close inspection.

Leg hair can be hidden by high denier (80+) nude tights (even worn under stockings), but ultimately there is no substitute for hair removal. What works best is very individual, but on the whole, shaving is not a particularly easy solution and is most likely to lead to ingrowing hairs, though hair will re-grow quickest. Waxing lasts the longest, but can be both painful and leave red marks on the day — not recommended just hours before your debut. Home waxing is not easy either.

Though it can be a bit smelly and messy, hair removal cream can give excellent results and is easily applied by yourself. It’s important to follow the instructions very carefully however, including doing a test patch before covering yourself with the stuff. There are creams for sensitive skin, but this is a chemical process, so pay attention, make sure you are thoroughly washed afterwards and remember to moisturise.

All of these preparations can be treated as ‘one-off’ events if you’re pulling out the stops for a sudden transformation. However, in the medium term, the biggest difference you can make is a commitment we can all struggle with — simple exercise and diet. This is worth a few articles of it’s own (please ask if you want to read!), but a healthy, balanced diet doesn’t have to be extreme to improve skin tone, reduce flab and simply look better, both as a male and a female. Exercise helps too, but of course this should be for flexibility and tone rather than body building. Cardio workouts, Pilates, cycling and swimming can all help, and again, being fitter is good across the board, so what better incentive to start than wanting to look good? Just remember to take your time and follow good advice rather than burning yourself out on a mad fitness kick.

OK, so you’ve spent a little time on your body, let’s dress it up.

This is where we start applying the wisdom of drag queens, and thinking about negative space (in a positive, fashion forward kinda way).

Alyssa Edwards

Sure, you might be planning to be just a little more dressed down than Alyssa Edwards(!), but take a moment to think about what’s happening with this outfit. Men are typically more ‘carrot shaped’ than women — broad across the shoulders, then straight down with a relatively low waist (pesky ribs).

Of course this is an extreme example, but this dress completely disguises Alyssa’s shoulders, pinches in to a waistline that’s possibly a couple of inches above her real waist, flares out over hips that aren’t there and shows off incredibly long legs. It leaves the impression of a doll-like figure, despite the fact you can’t actually see her figure at all in it. It’s like Penn and Teller explaining how a trick is performed, isn’t it?

It doesn’t need over the top ballgowns to pull the trick off either. This outfit is doing exactly the same thing — shoulders hidden, high waist line, flared skirt, broken up silhouette and heels to give the impression of incredibly long legs.

In fact it’s a common ‘complaint’ from women that crossdressers seem to have unfairly long legs. The reality is that we’re much more likely to be wearing skirts that barely cover our crotches, and heels that are impractically high. The effect is dramatic though, so if you’re not planning to walk far, or bend over, it’s worth making the most of what you’ve got!

It should be clear by now that picking the right outfit will work wonders if you focus on the shapes you’re creating rather than how pretty the clothes themselves are. Though it’s tempting to buy pretty party dresses from the fast fashion outlets, those are usually designed to look good on an entirely different figure. Not only will they probably fit incredibly badly, they will often end up emphasising exactly the wrong proportions to look good on a male body. Sizing can also be difficult — fashions for young women are cut for a different body shape and smaller size than fashions for more mature women, even though the dress size might stay the same. It’s worth checking the size guide for each shop or website before making a purchase.

Of course, there’s only so far you can go with carefully chosen separates. Luckily, in a society obsessed with women’s appearances, there are a plenty of options to dramatically change your figure. A waist clincher or well fitted corset can look amazing, but this is not a casual choice — high street ‘fashion corsets’ rarely work and often result in the unfortunate wearer looking like a badly squeezed tube of toothpaste. Authentic steel boned corsets, if properly fitted, can reduce a waist by four inches (with practise). Good quality corsetry is readily available through specialist suppliers, but it’s strongly recommended that you try them in person before making an investment. A slightly more accessible option is to use a high waisted girdle, which also has the benefit of reducing any unsightly bulges down below.

Finally, of course, we cannot avoid talking about boobs. The more modest crossdresser can achieve a lot with a decent quality bra and some carefully packed socks. It’s possible to get a more natural (and less lumpy) appearance with a pair of thick tights packed with bird seed, but most convincing of all will be silicone breast forms (or for those who are happy being more flat chested, ‘chicken fillet’ bra pads). Breast forms are not particularly cheap, but they will look and feel incredibly natural under a top. What they won’t give you is a cleavage.

Jeanne Lazareva — BoobsShop

For that, there is no completely convincing option (no matter what people might tell you). Dedicated crossdressers and drag queens can buy breast plates like the one above that are worn a bit like a vest top, and can look amazing in photos and flattering light. However, there are still edges (and a neck line) that have to be artfully concealed, and they’re unlikely to survive the sort of close attention that a ridiculously large cleavage will attract. Beware of cheap alternatives — unless a breast plate is correctly sized, well made and has the right skin tone, they can look extremely odd and off-putting.

Before we move on to hair and makeup, it’s worth pointing out that women’s fashion is a cut-throat business, so there are a lot of shops that will happily promise the world when it comes to looking pretty. Some are simply optimistic, but others (particularly some high profile online sites) will outright lie to get you to part with your money. There are plenty of examples of people receiving items that look nothing like the photos, and often photos are simply of celebrities and models wearing something similar (but much more expensive, and properly fitted) to the item being sold. With all of this, buyer beware — it’s always worth looking for independent reviews from fashion bloggers and YouTube before believing the hype.

If you had to choose an example of items that rarely look like the pictures, wigs would have to be the top choice. Nothing transforms as much as a beautiful head of hair, so the hair industry above all is full of promises that can’t be met. It has to be said that there are companies that make absolutely stunning wigs. However, there are also dozens of companies that flood the market with cheap and nasty wigs, using photos of other people’s products and even models’ real hair to convince you the wigs are perfect. Price is really not an indicator either, as a top quality human hair wig can cost a thousand dollars but a cheap synthetic one can cost cents, so there is plenty of room for manufacturers and stylists to mislead on price.

A key thing to realise is that even the best wig will only look good after careful styling. Without being cut and styled, nearly every wig will look messy, just like real hair.

With clever styling though, even low cost wigs can be made to look pretty cool. We’re so used to alt-fashion looks, cosplay and unnatural colouring that a carefully chosen outfit can work with a wig to look very convincing.

Turning a low cost, synthetic fashion wig into something like the picture above takes a bit of effort, but there are plenty of YouTube how-to videos that explain what is needed. Thinning and trimming hair helps, and there are techniques to reduce the ‘shiny plastic’ effect of synthetic fibre. If you are serious about looking good, and can spend the time to have a go at styling a wig properly, this can be a great route to take. Just beware, you’ll be picking funny coloured strands of fake hair out of your carpet for months.

Noriko — Angelica wig

For a more natural look, the well known brands like Noriko offer a much higher quality product which will look good with a lot less fuss for a higher price. Finding a bridge between cheaper fashion wigs and the better quality natural wigs is not easy — here, looking at reviews and checking out pictures of other purchasers is invaluable (check out Amazon reviews). It really is a question of taking each wig on a case by case basis.

Remember that for a convincingly natural look, you have to work with your regular features and think carefully about a style that will suit your face and fashion sense. Pick a wig that is a little lighter than your natural shade, rather than jumping for a peroxide blonde waist length monster.

Mizz Cracker

At the far end of the spectrum, and not even attempting to look natural, there are also hand-styled wigs sold for drag artists. These are great for a high fashion look, or just for the shock value, but an experienced stylist is not cheap. The rule about needing styling when you put it on still applies — a drag wig needs plenty of care and attention. Since drag wigs are used for fashion and performance, photos are often touched up to improve the difficult hair line and hide any lace, so don’t expect to be able to pass off this kind of wig in person. This option is only for the bold and you have to be confident to pick something that looks amazing, rather than making people cringe.

Makeup finishes the look, and is a fine art. Unfortunately, I’ve lost track of the number of women who’ve said “I can do your makeup!”, thinking that the problem with men putting on makeup is not having a steady hand, or enough practise with an eyelash curler.

Just as with clothing, feminizing a face is about playing tricks with shape and colour to hide the hints of maleness. Whilst drag queens dial this effect up to eleven, the techniques they use can be dialled down to produce a convincing look. If you’re young and fresh skinned, this is far less important, but even then, contouring can be deeply flattering. For those of us who aren’t quite so blessed, a stronger look might not be suitable for grocery shopping, but can work well for an evening out.

Of course, there’s no way to even start to cover all of the techniques for flawless makeup, never mind the range of styles you can chose from. YouTube and Instagram are vital resources here, for how-to videos, product reviews and inspiration for looks. This really is an area where doing your research can make all the difference. Then, building up a basic makeup set will pay off. Depending on how far you want to take your look, there are a few key techniques and products you’re likely to want to search out.

Start with foundation. Dermablend and Kryolan produce stick foundations that are capable of hiding full body tatoos, and can certainly hide a little beard shadow whilst leaving a face looking natural. However, if your face is just a single shade the illusion quickly breaks, so a contouring palette provides a variety of shades to improve things. Contouring is one of the ‘big tricks’ for feminizing a face, first really seized on by drag artists, and then moving into mainstream fashion for bold and feminine looks. There are plenty of YouTube videos for this, and it’s a technique that needs some practise, but the end result makes an enormous difference to a face.

To literally elevate your eyes, eyebrow blocking is the technique of covering over existing eyebrows, to re-draw more fashionable brows that give the illusion of a more feminine brow ridge and more open eyes. This won’t disguise really hairy brows, and isn’t the easiest trick to learn — requiring a good eye for a natural shape. However, again there are plenty of how-to videos demonstrating the process and getting it right can completely transform your look.

There are so many things you can do with your eyes, from shadow, to eyeliner, to false lashes, that can go from hard and minimal, through to softly glamorous and on to wildly extravagant. Whilst drag makeup tutorials inevitably tend to the extravagant end, they will often show some of the techniques used to open up eyes, lighten the patches (bags!) below them, and to widen your gaze. As with all makeup, if you’re planning on going to work en-femme, less is more. Alternately, if you’re trying to get great photos, makeup can often appear under done, so it can be worth going for a stronger look to please the camera — just remember that blending, shading and careful choice of colour is the difference between high fashion gothic and scary clown makeup.

It’s a trap!

Did I say makeup finishes the look? Of course it doesn’t! Just as artists are taught to think about negative space around the object they’re trying to capture, you need to be thinking about how a look is reinforced by the details around it.

It’s easy to obsess about a particular outfit, and then forget that it’s all the details that make it convincing and attractive. Jewellery and accessories make a huge difference and don’t have to break the bank to complement a look. Clip on earrings mean you don’t have to have pierced ears (but of course, piercings will make things a lot easier), chokers can help hide an Adams apple, gloves can flatter hands or you can get false nails to save the hassle of nail polish. Looking convincing can be about ‘inhabiting’ the look, which might mean having the right bag, belt, shoes or even cat-eared headphones.

Above all, whatever look you want to go for, it’s worth spending a bit of time thinking how women naturally bring so many elements together to look great. There are thousands of reference images you can work from on the internet, and a bit of research can throw up playful ideas around a theme, new ways o present it, or great poses to show off a look (worth another article in it’s own right).

If you really want a dramatic transformation, the key is to have fun with it and take time to explore it, rather than assuming that you can just transplant a dress from a girl to a guy and ‘get away with it’. Dress with confidence (or be confident choosing a dress), and above all, remember that a smile will work wonders, both in person and in photos!

Gender warrior, so long as the fight involves staying at home and comfortable undies.