How To Crossdress (Sneakily) 8

Being a crossdresser’s pretty tough – there’s this thing that you want to do, but it’s (annoyingly, and stupidly) frowned upon by most people (or at least, the internal paranoiac seems to think so). It’s also hugely visible – it’s difficult to not stand out of the crowd when you’re 6’3 in clicky heels. And yet, that urge to wear what you want and not be shunned or shamed is pretty strong. So what do you do?

There are a few ways that I’ve battled with it out and about – and one thing I’ve found that somewhat sates the beast within is to wear stuff that’s pretty unisex, or just slightly over the fence into that other land.

From the top! Or, I suppose, the bottom:


Ok, so 4-inch heels are probably out of the question if you want to keep it on the down-low. What you’re going to have to do here is go pretty unisex.
Probably my favorite pair of shoes is a pair of pink converse low-tops that I own. I’m not a huge, raving, fan of pink, but these are awesome, pretty girly, but still entirely passable as male footwear also. In fact, pretty much any converse low-tops in traditionally-un-male colors works pretty well. Don’t be afraid to buy bright (green/yellow/pink/blue)!



So no one’s really going to be examining your socks on any real intimate basis, so you can probably wear what you want here. I generally opt for light-colored, knee-high argyle type-stuff. No one ever sees that but me, so I figure I’m probably all good.



You didn’t think I was going to say skirts, did you?!
There are a few options here – jeans are a huge and diverse arena to play around with, and women’s jeans are infinitely (ok, that’s not strictly true) varied in cut. Skinny jeans are pretty awesome here – not super skinny ones that might fall under the term ‘jeggings’ (which is an horrendous portmanteau, for the uninitiated, of ‘jeans’ and ‘leggings’) – only a select few can effectively pull those off, but rather, ones that hug the leg without being obscene. Levis 511’s fare well if you want something fairly unisex. Then there’s women’s jeans themselves – given the large range of cuts and fits, it might be worth meandering into Sears on a weekend and trying some one while it’s pretty empty. I like jeans that are a little flared at the bottom, but pretty close-fitting up-top. Pocket embellishments are awesome, but I’m yet to find a pair of jeans where they aren’t over-the-top.



Maybe I’m pretty atypical for a crossdresser, but underwear doesn’t really do it for me. I’m not into the frilly/lacy panties that some people are. Though maybe that’s more of a factor of being 100% certain that I’d look ridiculous in them (to me, it’s all about the look). That said… There are still options! American Apparel do some pretty awesome unisex underwear which comes in a load of colors, both masculine and feminine.
That said… It’s unlikely that people are going to be peeking at your underwear throughout the workday, so be as adventurous as you want here! Although if you bend over and someone grabs your exposed G-string, that’s all on you!



I have real trouble with tops. I’ve tried women’s tees, and sometimes they’re ok, and sometimes they’re just a little too tight and make me feel self-conscious. Brightly-colored t-shirts are probably the way to go, or at least, I think so. Some guys can pull off cardigans – and if I could, I’d probably do a lot of that. Old Navy has some pretty decent stuff for tops, although I sometimes find they’re a bit boring and frumpy.


I find that it’s pretty easy to incorporate something feminine into your masculine attire, no matter what the occasion. It’s pretty easy to do and satisfies enough that beast within so that I’m not tearing my hair out every five minutes desperately wailing at why Naughty Monkey stop making shoes at size 10…

/me cries into Margarita


If you liked this, check out how to crossdress for real – which gives a bunch of tips for crossdressing effectively!

Check out more details about my journey here, my make-up guide here, or just a load of pics here!

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8 thoughts on “How To Crossdress (Sneakily)

  • Pat Scales

    We have a lot in common. I have a great need to have some article of feminine attire on most of the time. I think that it is a subtle reminder and affirmation that I am a CD. I wear pantyhose and panties daily (except when I expect to see a doctor or expect to be in a locker room). More often than in the past I will go out without socks over my hose. The other night my wife and I went to a restaurant and the only table available with a good view was a high table with high stools. Under my slacks I had on sheer beige pantyhose and sitting up high on the stools there was no way it could be concealed. At first it kept me a bit on edge but after a while I had that ‘peaceful easy feeling’ that I get from wearing woman’s clothes.
    Until recently all of my woman’s shoes were high heels. I recently picked up a black and brown pair of low heeled tassled woman’s loafers. Perhaps they are similar to men’s loafers but I know they are a ladies shoe and that is what matters.

    • Harrovianka

      Thanks for this. Stealth crossdressing is becoming more fashionable in more than one sense of the word. De rigour for women why not for metrosexual men?

  • Sandra

    Hi Liz, your suggestions for how to cross dress sneakily are right on. I wear woman’s cloths all the time except when I have to wear a “uniform” for the male group that I’m a part of. At 72 my desire to cross dress has increased to the point where I avoid men’s cloths as much as possible.

    My wife, who only tolerates my “gift” to a small degree, gave me a pair of men’s blue denim pants and two pair of men’s underwear for Christmas. I haven’t figured out how to return the pants yet for woman’s and I know that I won’t wear the underwear.

    My goal for 2017 is to provide my wife with more information on cross dressing so she will be more likely to accept who I am.

    Thanks for your site.


  • Steff

    Great site
    I m out to my wife
    She didnt know for 23 yrs
    Shes been very supportive thiugh disappointed i kept from her
    I agree with the stealth options and indulge the femme jeans and tops with the femme undergarments
    This wirks well for me since i dont “feel” the make up part
    Just wish i could wear herls out
    Oh and i get my pedis with color since no
    One sees that unless i want them too

  • Morgan

    I my version of sneakily crossdressed is UGG boots womens jeans non skinny ,and a hoodie … warmer months womens shorts T and womens Birkenstock sandals lucky for me I can wear women’s 42…