How to Crossdress… For real, this time! 5

Last time (my god, that was a long time ago) I talked a bit about how to crossdress sneakily… This time… maybe it’s worth talking about how to actually do it, or at least, how to avoid the mistakes I made, and those that I see others make as well. See this guy? The one on the left? That’s me. Clearly I had no idea what I was doing back then. whatamidoing Fetish boots? Crazy hair? Apparently I didn’t shave, terrible makeup. That’s probably the only pic I have of me even approaching dressed up. I don’t really know why I still have it – like the rest of the awful, awful pics that existed through the years, they’ve mostly been, by and large, carefully destroyed to maintain some semblance of my own sanity. Some asked me recently if I had any tips for beginners. My answer, basically, was “OMG LET ME TELL YOU ALL OF THE THINGS” So… here goes, I guess

How to crossdress:

Pay attention to what women wear

I know when I started, my first thought was “HIGH HEELS! BIG BOOBS! RED LIPSTICK! SHORT SKIRTS! BLUE EYESHADOW FOR SOME REASON” – and while those are true in bits and pieces, throwing it all together at the same time is kind of a nightmare. I think to be good, you have to cultivate a level of attention to detail, to see what looks good. It’s an oddly analytical approach, but it pays off. If your goal is to pass, then dressing up like your own ultimate fantasy isn’t really going to help. When you’re out and about, look at what women are *actually* wearing, and don’t trust your own mental image.

Makeup is hard, and it takes practice…

…and a good foundation goes a LONG way. Mostly it’s about subtlety and not being heavy-handed (or at least, trying to make it look like it’s not heavy handed) – /r/MakeupAddiction is a really good resource for that kind of stuff :D I put together my makeup routine which took a while to cultivate and master, and hopefully that’ll help someone else out there! Don’t just go straight for bright-red lipstick and dark eyes – makeup is a lot about light and shadow, defining good features, hiding blemishes and bad ones. You have to really understand your face, and what you’re going for. OH – and before I forget, for the love of god, clean up your eyebrows – be brave, go get them waxed or shaped or something – they’re not going to care, and you’ll look a LOT better when dressed as a male as well as a female.

Dress for your body

I see so many people wearing these tiny tiny dresses, but underneath they’re big fat guys – NOOOOOO – it looks awful :( If you’re a bigger guy, maybe look at clothes bigger girls wear – taking a look at the kind of stuff sells is a good starting point. It’s kind of crucial to understand your body shape too, and what kinds of things look good. If you’re skinny with a waist, it’s definitely worthwhile exploiting that! If you don’t have much of a waist, aim for more A-line cuts of skirts/dresses that make it look like you have hips. If you have good legs, you can exploit them with heels/tights/skinny jeans. I think it’s also important to not show too much flesh – a short skirt is fine while being fully covered on top looks really good.

High heels are great, but just how high?

Heels are AMAZING, but they don’t all have to be 6 inches (and if you can actually walk in 6-inch heels, good on you!). Flats are really good accompaniments to lots of outfits, and look really cute (and are a LOT more comfortable). Look around you and see how many women just out in the world are wearing stupidly high heels at 3pm on a Monday… not that many!

Accessories can really help distract from masculine features

Rings, necklaces, earrings, bracelets, hair pins, etc, can all help draw the eyes away from your least-favourite-features, though it’s important to not go overboard and look like Mr. T! Try to find a good balance! Necklaces draw the eyes down and can accentuate your chest a bit. Dangly earrings can elongate the face.

Be yourself!

Don’t try to be someone you’re not. It takes a while at first, because you’re still trying to figure out wtf is going on, and learn all this stuff a lot later than most girls learn it. But take it slow, and spend a lot of time observing – if you have female friends, and you’re not too uncomfortable talking to them about this, they would be more than happy (in my experience, at least) to help you out! Ask them about their clothes, where they get them, advice, what looks good with what – they’re an invaluable resource, and can help you find your personality a bit :) hope that helps!


Why not take a look at my journey so far, or maybe even how I go about doing my makeup – or even just some of my pics!


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5 thoughts on “How to Crossdress… For real, this time!

  • Anna

    Those are some good tips. When I first started out and I think for many crossdressers its all about the heels and the short skirts but its just so much more then that and i’m still trying to find the balance.

    I’m 28 at the moment and over the years I have done the odd bits and pieces to try and been a women. Brought the high heels, the odd skirt, the sheer tights but now as I’m getting older its started to become a bit more serious. I have recently started to look at woman and not just if I would fancy them(typical bloke) but what they wear and how they act when walking etc. Its certainly a fine art to master. I brought a camera to help, to see what I look like and how I would act as a woman (it has helped tremendously) and I was watching myself walk in heels and yes it is entirely possible to walk like a bloke in heels.

    It is quite hard to adjust, sometimes it feels wrong but then most of the time is feel so very right. I’m at the stage now where I have a few outfits and quite abit of makeup (which I just slap it on willy nilly but I think i’m getting there) and I like to say these tips helped quite abit. So cheers.

    Oh and thanks for the wig website, I have one but I think I look like a haystack that has been planted on my head so I think a new one is due soon.

  • Sarah

    A lot of useful tips and anecdotes on the site – especially the makeup section – many thanks!

    I started crossdressing when I was about 8 or 9, but pretty much gave up on outerwear due to a combination of problems stashing stuff and the initially disheartening size gap between myself and my mother/sisters. For some reason I just resigned myself to underdressing (part from the occasional borrowed dress) until 4 or 5 years ago – 35 years later. What I did cultivate in between apparently was a ‘good’ female dress sense by taking an interest in what women wore and commenting when asked. I must have done something right because my (mostly) female close friends, and particularly my mother, have always said I have a good eye for what suits them best, uncommon in most men I’m told.

    So when I finally opened Pandora’s box, ‘what’ to wear and colours and patterns wasn’t much of a problem, and I largely managed to avoid the ‘everything to excess’ stage, although for some items fit took a good deal of adjustment from what I was used to – most notably the tendency to lazily go for ‘too loose’ rather than a proper fit – boy does that make a difference – which is hard to do without going into shops and trying things on, a hurdle in itself.

    What I hadn’t got before, which Anna and the article touches on above, is ‘how’ women wear clothes in terms of the differences in body shapes compared to mens, and where clothes actually sit – my tendency was to wear the waist of skirts too low on the hips, particularly for longer lengths; getting used to lower necklines and perhaps combining them with a pretty camisole – the idea of a low or even open neck as a bloke was just plain odd. The trick I’ve found is to really pay attention to how women whose style you like (and particularly those nearer your build) wear clothes when you’re out, but pay more attention to fit and where items sit than how it looks overall – don’t forget hair length and style. Google images is particularly good for this when you’ve nailed the right search clues, you can review loads of pictures very quickly and concentrate on ones that fit what you want. Whatever you do, dress to your age and to make the most of your body shape rather than trying to fight what you have. When it all comes together its remarkable how natural (relatively!) it can look.

    Beyond the clothes themselves, a big eye opener to me was the difference accessories make. Ditch the chunky watch for something altogether more obviously feminine, buy a few rings and bracelets, a necklace or string of beads, a decent handbag, again taking care to make sure they’re not too chunky. You can easily get away with 3 or 4 bracelets in different styles on one wrist, and done right it really adds something. Perhaps the biggest surprise, although not exactly an accessory, was painting your nails, which combined with a bit of jewellery really takes the edge off larger hands. Not everyones cup of tea, but a tasteful silk scarf adds to believability, and is a useful cover up if you can’t (or just haven’t) defoliated your chest – I do, but still love the 3 or 4 I have. With a bit of perseverance, most of this stuff can be had relatively cheaply on ebay without ending up too cheap or garish.

    My two real bêtes noires are shoes and makeup. I have quite wide feet in a large size, and nice shoes at a decent price tend to stop short of my fit. Its best to try shoes on because womens sizes seem even more random than mens – I have (UK) size 9s that fit beautifully, and 11s that are a bit of a squeeze over time. Scouring shoe store sales might get you a result at these sizes, but secondhand on ebay can get really top notch shoes for good prices if you pay very close attention and are prepared for a few misses. Looking at a sellers other items often gives a clue as to which end of size X the item you want is.

    Makeup is still at the ‘nightmare stage’ for me – if you have any tips for applying eyeliner if you wear glasses and need them to do the detailed bits, I’m all ears. The only tips I can offer are; don’t skimp on quality, and theatrical foundation (I use Kryolan, but there are several other well known brands) is great for beard shadow and blemish cover, and has really good staying power.

    Wigs can be a challenge to nail what is likely to suit, but again looking at those around you can help a lot. I originally assumed I would need a longer wig to frame my face properly, but my final favourite is barely shoulder length. Colour is harder, but sticking close to your natural colour is usually a good starting point. There are some very good wig shops that cater to crossdressers, so check a few forums for initial recommendations because the good ones tend to be mentioned again and again. Try to make sure they take returns. Cheap wigs can be a good start when you’re figuring it out, but the quality usually shows. Once again a bit of patience and luck checking the excellent ‘sale’ pages that every wig shop seems to have can get you a very expensive brand for a fraction of the normal price – my last one was less than 20 percent of the price elsewhere – but do make sure its a style and colour you can live with, not just a bargain.