Far and away the easiest and safest way to crossdress is to underdress. This simply means to wear women’s clothing (usually underwear) under your everyday clothes. Many crossdressers do this frequently and thoroughly enjoy it.
As far as not getting caught, this is a no brainer. I can’t thing of any other mode of crossdressing that can be done in public with no one noticing.
Undercover Crossdressing
Underdressing usually entails wearing women’s panties or bra underneath your outfit for the day. Sometimes it can be taken even further with a full lingerie set, whatever you’re most comfortable with.
Men’s clothing is almost always loose-fitting on the body, even dress shirts are somewhat relaxed fitting, allowing transvestites to secretly don their favorite skivvies.
I know what you’re asking: “But Jessica, how can I underdress?” Well, lucky for you I’m such an expert in transvestism, here are step by step instructions on how to underdress.
Step 1 – Select Your Undies
Go into your underwear drawer and select a bra and pair of panties. Optional: Garter Belt, Nylons (pantyhose), and Corset.
Step 2 – Put Them On
Now, you’ll want to be naked for this step. Proceed to clasp the bra and pull the straps onto your shoulders. Next, put on your panties. It’s just like putting on briefs or boxers, so this part should be a breeze. Optional: Finish up by attaching the rest of your lingerie set.
Step 3 – Put On Your Boring Man Clothes
This is usually people’s most despised step, but it must be done, to avoid indecent exposure. Slip into your pants and shirt, make sure nothing is peeking through, and leave the house. Proceed to enjoy.
That’s it! You’re now well on your way to underdressing, have a great time!
Note: If you want to be extra daring, wear a push up bra that will give you two small bumps on your chest. Also, you can wear light colored clothing that will show what you are wearing underneath.
photo credit: dr_vaibhavahuja
{ 49 comments… read them below or add one }
I’ve gone out to walk the dogs a few times wearing my corset under clothes. It was a windy day that pushed my shirt back and showed my figure very well.
Sounds pretty curvy
Well thank you, Miss Obvious.
Hehehe, no problem
You have pretty much described the beginning of most of my days. I wear pantyhose nearly every day. Last winter, I delved into camisoles and short slips, and the occasional bra. But in the heat of summer, it stops with hose. Underdressing is great, but it’s no longer a secret if you collapse with heatstroke.
Whatever sanity I retain, I credit to underdressing.
LOL, yea, collapsing would be a problem.
Yes, that’s how I usually under-dress. I am a bit more daring when I outer-dress. Good post!
Thanks, Sheen!
Back in the day, I’d do this, but now I’d feel kinda odd wearing a bra under a shirt. Not that there’s anything wrong with that, it’s just me. I guess I’ve swtiched to be an all-or-nothing cross-dresser!
Well, not completely ‘nothing’ – that really would be pushing the envelope!
That’s how I feel, I don’t usually underdress unless I’m just bumming around the house.
Hihi, I remember the first time I did this I was so conscious of someone noticing. Nobody did, and if someone ever noticed, they were probably abashed or too embarrassed themselves to say anything.
A good thing about the human perception is that the brain doesn’t notice things that it’s not looking for, so even if someone saw something slip out of place it won’t pick it up.
I wore a bra under my t-shirt and went to class one day. As it turned out, I sat in the front row and was convinced that everyone could see what I was wearing. In reality, it’s unlikely that anyone did
For years I dressed using some sort of female clothing on my body. Since high school I’d wear women’s socks, panties, shorts, or even keds (loved those keds!), but all the while it was just something I did to try and alleviate the dysphoria of being forced to wear men’s clothing (something I didn’t ever see myself as). I do remember feeling a slight bit of relief just to wear even a small article…I guess anything to try and feel whole and congruent. ( I know it’s different for others.)
Oh, I forgot to mention I always wore women’s athletic shoes. People were very rarely aware I was doing that, and I even got complimented on the shoe colors I wore. Face it, Nike, Reebok, and Adidas do a pretty crappy job with men’s colors. Seriously, lime or puke green? Yellow and black? What am I, a bumblebee? LOL
That’s very interesting to me, dressing as a way to alleviate those types of feelings. When I would do this as a teenager, it was more of pushing the envelope for me.
Yea, the typical gym shoes you see in the stores are pretty lame. That’s why you have to go for the limited edition shoes, but that’s a post for another day
I under-dress every day. Its become almost natural for me. I feel a little off the mark if i dont under-dress. I usually wear bra and panties with a tank top unless its summer and hot out then the bra is usually left home…i dont want to be found out by someone noticing a bra under my T-shirt on a hot day. Though i am starting to not care what other people might think or say. I’m all for it lol.
When you start ignoring other people’s opinions, it feels so liberating
Underdressing is something I’ve been doing since I was very young. One thing I do in underdressing is wear toe polish. You notice it the first thing every morning and in the shower it gives one a very femme feeling.The only drawback is my Yoga class. Im the only one wearing socks. Thats OK as its all girls and me. Iwould love to show up wearing a leotard some time but that would be overdressing.
I painted my toes the other day and left them for like a week or so… I would notice them every day and then forget they were painted
Hi everyone! I love getting up in the morning and deciding what panties to wear underneath. And when it’s cooler, I LOVE to also wear stockings and garters…..
the other day I was feeling really naughty and had fishnets on and a bra and I went to the grocery store. I didn’t realize till I got there that the cuff of my pants barely reach my shoes, and so I felt like everyone could see my fishnets!! I’m sure they couldn’t, but I was both excited and nervous at the same time
Cool, Kristina, thanks for sharing
Hi Kristina
Sounds like you had an exciting adventure at the grocery store
I underdress every day. I stopped wearing men’s underwear about 8 years ago. About 6 years ago I stopped wearing men’s jeans. If people notice they do not say anything.
Good for you, doing what makes you happy
Decided to underdress today and thought of this older post and thought i’d leave a comment. Some days you just need a bit of femme to get by!
Very Cool Rachel
Underdressing is indeed the easiest way to crossdress. Going out in public dressed as Kathy is a no-go for me as I have facial hair and I’d likely not be passable anyway, however, wearing pretties under my guy stuff is liberation. I’m retired now and try to dress daily. When I was still working I would sometimes underdress beneath my police uniform and when I was a detective I frequently wore panties, garterbelt and stockings under my suit pants.
If you see me out and about now in shorts and an aloha shirt you can bet I’m wearing a nice silky little unlined, underwire bra, panties and pettipants or a lacey halfslip.
Kathy
Glad you find it liberating, as do many other crossdressers. It’s an easy way to indulge yourself without getting caught in public.
Whenever I underdress I feel like something’s missing. It’s neat and all, but I feel like I’m cheating myself. Perhaps it’s because I’m playing it too safe? Or perhaps it’s because it is only a 5% expression of who I feel inside.
Though, I’ll never forget the time I was younger and underdressed without anyone being the wiser…
Same here, this is why I rarely, if ever underdress. For me, it’s pretty much all or nothing, unless I’m just lounging around the house being lazy.
I love wearing pantyhose under my jeans when i go out or even tights under em in the winter for extra warmth.I tried on shoes at a store while wearing pantyhose under my jeans as the girl who helped me didn’t say nothing just kinda smiled. I have gone thru a drive thru wearing bright pink or blue or black fingernail polish as the girls kinda giggle or say “cute nails” I have even worn a touch of mascara and went into a store as seems like the younger girls only notice .I paint my toenails and leave em painted for a week or two and repaint em a different bright color.I am planning to go out wearing skinny jeans as they are a unisex style but knowing the tight jeans from waist to ankle are more a girls style.
Good to hear Kelly, keep on being true to yourself
L’eggs Trouser Socks — they are just the right thickness, they don’t droop like men’s socks do, and they allow me to feel a little feminine when dressed en homme.
They sound cool
I refuse to wear men’s socks anymore. I think they are so uncomfortable. Too thick, don’t let your feet breathe. Now if I must wear “socks” I wear L’legg’s trouser socks or knee highs.
Nice
Although I dress completely as Pam when I am home I haven’t gotten the courage yet to underdress when I go out in my original male mode. I want to wear panties under my male clothes and no one would ever know, but I need encouragement to do it the first time.
I say go for it
I went to Hooters the other day and wore jeans with holes in the knees and had on shiny dark tan pantyhose under em as I have always envied the Hooters girls for being able to wear their pantyhose everyday at work. My waitress noticed I had on the pantyhose as she giggled and thought it was cute as I noticed other waitresses walking by looking at my pantyhose thru my holey jeans and smiling.A few of the girls told me to come in next time with shorts on while wearing the pantyhose but I am not that brave.
Great story, congratulations Charles
I manage a large crew of utility workers and underdress every day. Usually a nice Cami and Panties and Hose in the cooler weather. I have managed to be pretty discreet by wearing dress shirts but I was rushed the other day and quickly threw on a company branded golf shirt. I got a few funny looks that day but didn’t realize that the strap adjusters for the Cami were clearly visible in the line of my shirt in the back until I got home!
Best part of the story? I found that I didn’t care…I am what I am.
Very cool and thank you for sharing your story Michele
I underdress every day. In fact, I dont own a pair of mens undies any more. I find wearing Vanity fair briefs to be very satisfying. There are a wide variety of colors to suit me, blues, pinks, purples.
I have taken up wearing anklets daily too.
I feel so much better about myself now than ever before.
Underdressed for years while at work. Panties 24/7. Pantyhose and girdle frequently. Never had a problem even tho I was in front of a college class teaching not sittting behind a desk.
I under dress most days with a nice pair of nylon panties, cami with pantyhose and half slip. I have on occassion worn a nice under wire bra that matches my panties, either white or black. I really miss days that I do not feel the silky nylon panties against my skin
Steph
I’d never thought of the term, but I have sporadically “underdressed” for decades. In the past few years, its become second nature – I haven’t any male clothing in my dresser, and pulling on a thong, panties, stockings (stay ups for warmer weather) and a camisole is just part of my usual morning routine. On days when i work at home I simply put on a dress and I’m there!
I am at work now with a bra, panties, waist nipper and lovely pink Capri tights. I would think my employer would encourage this since I am more energetic, friendly, and alive (not to mention productive) when I know what is next to my skin is so soft and pretty.
The only challenge is using the toilet with pink clad legs that can probably be seen through the seams of the stall walls!
ive been under dressing most of my life.there is not a day gos by that im not wearing something fem and silky under my man clothes,i also have found that if you look around you can find womans clogs or mules that will pass as mens shoes,and they are great with hose or trouser socks.ive found its very liberating to paint my toes with clear polish,and wear womans flip flops in public.ive gotten noticed by woman befor but i dont care what they say or think.i love it!.
I know this is an old post but I wanted you to know that I have just started to underdress and I like it. What comes next? Time will tell! Warren