Crossdressing Tips

Lately quite a few people have written me asking for crossdressing tips so I thought I’d share a few thoughts on the subject. This is by no means a complete A to Z of how to crossdress, just some things that I like to do. I always point out too that by no means am I the world’s greatest crossdresser, so don’t take anything here as the gospel truth. There’s no one right way to dress. I’m not going to go into makeup details very much as there’s lots of information online. Just Google “Crossdressing Tips and Tricks” or “Crossdressing Makeup Tips” and you’ll find lots more. Okay, this is going to be a long post, in no particular order…

Beard Cover – The absolute number one tip that I swear by is to use beard cover. Hiding that dark blue-ish beard tint is really tough, but if you use a good beard cover you can tame it. I’ve done some laser work to help thin my beard (it’s really heavy), but I still always use Ben Nye’s Studio Beard Cover (FS-1). You just shave really really close, then put on the beard cover, which has an orange tone. The orange color neutralizes the dark beard color and then you add your regular foundation OVER that. I also use Ben Nye foundation, which is a good theatrical makeup. Just be extra careful not to mix the foundation and beard cover or your makeup will turn orange! The Ben Nye foundation is oil based, so you’ll have to use powder to set it once it’s on. If you’ve done it right the dark beard shadow should be gone or almost completely gone. It really works.

I buy Ben Nye and other makeup at Naimie’s in Los Angeles. But if you do a Google search you can probably find a place to order online.

Shaving – When it comes to shaving, the sad fact is that you pretty much have to shave till it hurts! Well, maybe not that much, but to be honest I’ve often shaved my face so closely that I’ve felt sore the next day. There are lots of good tips online about shaving, such as using a warm cloth on your face for several minutes first to soften your beard and open up the follicles. I always make sure I’m using a new razor blade and I go over my beard in several different directions. I probably don’t have the greatest technique – I basically just go over it and over it till it’s really really smooth. If you run your hand along your face and still feel the hairs you need to shave some more. You want it to be as smooth and soft as possible.

If you’re able to shave your entire body, it can be fun and very sensual, or it can be a royal hassle. The easiest and most enjoyable way to shave, I find, is while relaxing in a bathtub. The rub for me is I only have a shower in my apartment, so I rarely get to soak in a tub, but I yearn for the day when I live in a place that has one. A glass of wine, some candles and soft music, that’s the way to do it.

Eyebrows – Another nice way to improve your look is to get your eyebrows plucked. If you’re going to try to do it yourself, use a good pair of tweezers but be careful and don’t overdo it or you can end up looking really freakish. It’s best to pluck hairs from the bottom of your eyebrows to make a nice curve. If you have lots of stragglers on top you can use a pair of small scissors to lightly trim them. Again, go slow and see how you look before really hacking away.

It’s really nice to go in and have a professional shape your brows if you can. Lots of salons offer this service and it’s usually not too expensive. I think the last time I did it I paid $25. Lots of guys get their eyebrows shaped now so it’s not a big deal to go in for this. My philosophy, though, is to just be honest if you can, so I recommend telling whoever does it that you’re a crossdresser and you just want to clean up your brows and get a softer look. Most people won’t bat an eye – they’ve seen it all. Of course you don’t want to go into any details about your sex life or anything (they don’t want to know), but if you’re just honest and treat your dressing like it’s no big deal (which it’s not), they’ll likely respond in kind.

False eyelashes are another fun way to improve the look of your eyes. I’ve only started wearing them more in the last year or two and I love the dramatic look they give your eyes. When I’m putting them on, I apply the glue to the lashes while I’m still doing my eye makeup, and let them sit for several minutes while the glue gets tacky. Then using tweezers I start on the inside of the eye (near your nose) and work them out, placing them right on top of your natural eyelashes as closely as you can. It can be a real pain getting the hang of it but the more you do it the easier it gets.

Jewelry – Another simple but nice touch is to wear jewelry. Just a few pieces can make a big difference, especially earrings (clip-ons are fine if you can’t or don’t want to pierce your ears). A choker or scarf at the neck is also great for softening the look of the male upper chest and throat. I remember shooting some pictures once where I forgot to wear jewelry on my neck and the difference was so big, in my eyes, that I never even posted the shots.

Breast Forms – You can get away with stuffing your bra, or using the pantyhose and birdseed trick, but if you can afford a pair of breast forms they’re really nice. I purchased a pair several years ago from Glamour Boutique that I really like. They also sell these great bras that have pockets sewn in that hold the forms. I’ve never actually used the glue that you can use to attach them to your chest but I know some girls love that technique.

Wigs – Getting a good wig will help a lot for finishing your look. My own preference is for wigs with bangs. Male foreheads are often too large (mine definitely is) and the bangs really soften and give a much more femme look. I like Wilshire Wigs and Vogue Wigs.

Shoes – If you’re just staying in to dress for your own pleasure then you can get the highest and craziest heels you like. If you’re going out to the clubs or someplace, though, you’ll want to get some heels that you can actually walk in and still look good. I have both kinds, as I find that once I get to a four inch heel or higher it’s really tough to cross a street without feeling like I’m going to topple over into the crosswalk and land on someone’s hood.

Girdles and Corsets – One necessity for most guys is to wear a girdle or corset to tame the weight that so many of us get around our bellies. I have both though personally I tend to prefer just a tight girdle, as I have a bit of a fetish for them. Either one can help a lot, and if you have a corset that allows for tight-lacing (which tend to be expensive), it can work wonders. One of my favorite places for girdles is Orchard Corset. Versatile Fashions is also good, though expensive (and I’ve heard rumors that they may have been recently purchased by another company.)

Along the subject of body size, one of the best things you can do for a feminine look is to try to keep your body on the slim size, if at all possible. Believe me – I totally understand that for many guys, especially as we get older, that that’s just not going to happen. But if you’re carrying some extra weight it’s a good idea to try to work it down, even just a little. Your health will be better, you’ll feel better, and you’ll definitely look better when you dress. I’m still in pretty good shape myself, although there’s a little five pound roll that’s probably never going to go away now that I’m in my forties (unless I were to starve myself and work out two hours a day, which isn’t happening anytime soon!)

Speaking of starving oneself – don’t do it. I’ve seen a few girls who become obsessed with losing weight and who take it too far. I would say that being underweight is much worse for your appearance than being overweight, as the male body without any fat just becomes skin, muscle and tendons. Not pretty, and really bad for your health.

Okay, I hope all this talk about body size isn’t sounding like a lecture, or shaming anyone, as I don’t intend that at all. In the end, just try to make healthy choices, know your limitations, and be good to yourself. One frustrating thing about crossdressing is that the male body is obviously just different looking from the female body (duh!), so there’s only so much we can do. A few lucky souls can pull it off and nearly always pass, but for most of us (and I include myself, as I’m six feet tall), there are limits that we’re never going to pass. The main thing is to enjoy it, have fun, and don’t beat yourself up.

The Bulge – Another good thing to do to create that feminine look is to tuck yourself in to minimize the bulge. I usually wear a tight reinforced panty girdle and before putting it on I just push everything back between my legs as far as I possibly can. I’m not bragging, but I’m actually pretty big down there, and tucking – really pushing it back far between my thighs – makes a big difference. You can also buy a tight fitting garment called a gaff that helps compress and keep everything under control.

Shopping – I tend to prefer to go shopping in guy mode. I know some girls love to dress and go out but I always worry about getting my makeup all over everything, and to be honest, even though I’ve been going out for several years, I still find that I don’t really enjoy the public scrutiny all that much. It’s great fun to go out to a club but I’ve never had the personality to really thrive on walking into Ross fully dressed at noon. But that’s just me. If you’re the kind who loves to go out in the daylight, more power to you. I could use some more of your super-powers!

Many people have pointed out that when you do go shopping, attitude is a big part of it. You don’t have to draw attention to yourself but you also don’t want to shrink and slink around like you’re doing something shameful. You have every right to shop and look at clothes. If you act like you belong there and that it’s no big deal (even if you’re just faking it), then people will likely treat you that way. No one knows if you’re shopping for a wife or girlfriend or for yourself (well, at least not until you go to the dressing room). ;-) But the truth is most people won’t even notice. We’re all wrapped up in our own lives and most people just don’t care that much.

If you’ve never been in the store before, especially if it’s a bit more upscale, it’s often a good idea to ask if it’s all right to try something on. Many store clerks won’t even bat an eye. If they do, just thank them and go spend your money elsewhere. I’ve been told no before, and it can sting, but in the scheme of things it’s not that big a deal. In a place like Ross or TJ Maxx, I would just take the clothes to the dressing room and assume that it’s not a problem. They might notice what you’re doing but they’ve seen it all before. I also often shop in these local thrift stores here in L.A. called Out of the Closet, which are about the gayest stores in the world, and they definitely don’t care.

Online shopping is always good too, as there’s none of the potential anxiety of going to a real store. I still buy many things online but the returns when skirts or blouses don’t fit are a bit of a hassle. If you’re patient, though, you can get anything you want. And sometimes you luck out and it fits the first time (rarely for me, though, it seems.)

Well, I’m sure I’m forgetting something but I’ve been going on and on here and will be amazed if anyone’s read to this point. I hope some of these ideas are helpful or give you something to look into. I also have a few other places that I like to shop on the links page at Trannies In Trouble, under – you guessed it – Shopping.

Enjoy, have fun, and be gentle with yourself.

One thought on “Crossdressing Tips”

  1. thanks for the info, sandra; you’ve provided some useful tips and resources.

    the only thing i would suggest is that if you are paranoid about your dressing and want to keep it as secret as possible, using google will ensure that your search preferences and other info are stored somewhere and available to all forever.

    just because you’re paranoid doesn’t mean they aren’t out to get you!

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