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So, I have a work trip coming up to several places in a week. I put in some pause time for me and would like to make my first attempt of going out in public, but I'm stuck on what to wear. Really cant decide between jeans and heels, or a casual dress?
It will just be for a walk around the area, maybe a drink if I get brave enough. I don't want to stand out so it would be casual any suggestions?
It will just be for a walk around the area, maybe a drink if I get brave enough. I don't want to stand out so it would be casual any suggestions?
I looked at your profile and see that you can wear a wig, so if you don't want to stand out, maybe you might do less en femme for your first trip abroad. Baby steps.
Most GGs are wearing very low-key, casual clothes today, so doing the same would help you to fit in and stand out less. Assess your closet again, to see what you have that is less likely to draw attention, including shoes, since you will be walking.
Going out the first time can be a hurdle, but you got this one, Piper!
@pipertime a nice business suit shouldn’t attract too much attention with some low heels 😀
Here are my rules for going out, first time or otherwise.
1. The most important thing you wear is confidence. Act natural, like you're supposed to be there, and like you're not doing anything wrong or weird, and that's how others are most likely to act towards you. If you act nervous, you'll look suspicious, and that's how others will treat you.
2. Figure out what styles work with your body. Every single one of us has an outfit we wish we could wear, but if we're honest, we know it just won't look good. This takes a bit of humility and honesty, but confidence fits better with clothes that work with you rather than against you.
3. Consider what other women your age are wearing where ever you decide to go. What do women of your age wear to the grocery store? for a walk downtown? to the club? to the park? to the restaurant? to the symphony? to work? I have a lovely symphony outfit that I really, really love, but I don't wear it to the grocery store. I love the pencil skirts and blouses I often wear to work, but I don't wear those when window shopping downtown. Again, confidence is easiest to put on when things fit (both your body and the event). I mean, if you're like me, you're always looking at women's outfits anyway, so you should have a good idea of what makes sense.
4. Don't feel bad about not going out or not wearing a planned outfit if you put it on and it doesn't seem to work. In the movie Ratatouille, the food critic says something like "I don't like food, I love food; and if I don't love it, I spit it out." Getting confidence to go out is a complicated endeavor, but there's a certain feeling I get when I "love" an outfit, that makes it a lot easier to have confidence. Sometimes I try an outfit and think "no . ." or "hmm, maybe." I've learned not to keep these items. But sometimes, I try and outfit and think, "I can't wait to go out in this!" That's the kind of clothes I don't return. If I don't love it, I don't wear it. This makes confidence so much easier to find. It can take a while to figure out what works, but be patient enough to find stuff that really does make you feel confident. Your first time out can be scary. No need to rush or feel pressured.
5. Be more conservative than you think. I'm not talking politics here but a very common experience most of us have crossdressing is to try and wear smaller, more revealing, and edgier stuff when we first start out, only to discover later that we look much better with less extreme styles. Nine times out of ten, go with the longer skirt or the roomier blouse. If your goal is to look classy, and you go out in confidence, "sexy" will come naturally.
6. While I love wearing heels, if your plan is to walk around town and see the sights, go with flats. At the very least, carry some flats in your purse so you can change after a while. I have heels I love that are super comfortable, for about 400 yards . . . This is fine at work because that's all the farther I ever walk around the office between sitting and typing, but for enjoying the downtown scene you'll want something else.
7. This last one is my opinion, but along with point 6: go with smaller breast forms. To me, one of the tell tale giveaways someone is a crossdresser (or a new crossdresser), is their breasts will be too big. Sure, there's plenty of exceptions to this and women come in all shapes and sizes, but to look the most natural, you want to go for balance between breast size and body type and shape. If you have a breast fetish or something that's your own business, but if you want to look normal in public, you should strive for the most natural and balanced body shape and silhouette you can get. Along with this, invest in some hip padding and a waist cincher. I dressed up at first without these and looked okay, but once I tried them, I knew I'd never go back. It makes a huge difference, but again, you might need to experiment with what works with your body.
8. Oh, and one more thing: Plan in your mind how you'll respond to interactions with others. Will you use your male voice? If someone asks if you're a man or a woman, how will you respond? If a bunch of young men outside a bar start laughing and catcalling, what will you do? Plan your outing around safe spaces and be prepared. In short, think about going out the way women have to.
Stay safe, and have fun.
@raven188 thank you, i have thought through most of those except number 8.... never thought about the marlboro man talking, lol
@pipertime I didn't either until the first time someone said I to me and I croaked put some incoherent grunt. I find if I think through those sorts of things, it adds to the confidence and makes whatever happens easier to deal with.
Thanks, Sarah. Ideas based on experience. Good stuff.
Here are my rules for going out, first time or otherwise.
2. Figure out what styles work with your body. Every single one of us has an outfit we wish we could wear, but if we're honest, we know it just won't look good. This takes a bit of humility and honesty, but confidence fits better with clothes that work with you rather than against you.
What we wear at home is one thing. Going abroad takes more thought and probably a good amount of planning.
5. Be more conservative than you think. ... Nine times out of ten, go with the longer skirt or the roomier blouse.
Or pants. If a crossdresser really wants less attention, then she can learn how to obfuscate, create illusions, compromise, to become less visible.
Standing out is incredibly easier.
7. This last one is my opinion, but along with point 6: go with smaller breast forms. To me, one of the tell tale giveaways someone is a crossdresser (or a new crossdresser), is their breasts will be too big. Sure, there's plenty of exceptions to this and women come in all shapes and sizes, but to look the most natural, you want to go for balance between breast size and body type and shape. ... but if you want to look normal in public, you should strive for the most natural and balanced body shape and silhouette you can get. Along with this, invest in some hip padding and a waist cincher.
Not just your opinion, Sarah. Being 6' tall and 185 lbs, most of the time I use a B-cup breast form or smaller. Even at that a woman commented this week that my breasts were nice but bigger than hers, so if she noticed, everyone else who notices us will, too.
Body shape was one of the first things that I worked on. Hip and butt pads are important for widening our male hips*. Waist-cinchers are less necessary under a lot of loose tops. They can't hurt, but our waists will be less noticeable while covered up with these wide tops.
* If you wear something tight or revealing, such as leggings or stretchy skinny jeans, make sure that your pads don't give you odd edge lines. Loose skirts or dresses still look good over this type of hip or butt pad.
If someone asks if you're a man or a woman, how will you respond?
Of both times that I encountered this question I was asked if I was a man or a girl, which is illogical regarding someone who is visibly 70 years old, over 6' tall and still sports a mustache.
My reply was, "Does it matter?" "No, no, I was just asking." Yeah, right. But that is my fault, my cross to bear. Confusing is as confusing does.
@pipertime There will be a lot going through your mind on your first outing. My advice would be to keep it simple not to draw attention to yourself and to blend in with other women in the area. As an example, lower heels would be good since they will be easier to walk in and less likely to hurt your feet. Blending in is a great confidence builder which will help on future outings.
Personally I feel more feminine and freedom in a dress/skirt. I'm good with 4" or lower heels.
Don't walk hunched over. Walk upright and proud!
Snickering, cat calling and other rude behavior isn't worth responding to! Look them in the eyes, smile and never stop moving! It really throws them off balance!
By and large nothing but good will happen for you!
You can do this girl!
One final note. If wearing pants, make sure they don't bunch up at the knees. After sitting they may need the wrinkles smoothed out.
Remember you a Lady!
Fran 🥰
I personally think a casual dress that doesn't stand out. Something to blend in.
I also will be making my first outing next week. Thinking conservative midi dress with a built-in slip. I have kitten heels to wear but in the last 2 weeks developed super sensitive spot on one of my toes. I taped a little bumpie-piece onto the side of my shoe stretcher which I hope will get me back into those shoes. But I'm really looking forward to this outing.... I hope it goes well and launches me on my way.
Dani
@danikiss22 Sounds like you have a good plan Dani! Best of luck and enjoy! It's an absolutely exhilarating experience.
@lauren114 Thanks hon! I am full of confidence, ready to do this. I would in fact live full-time right now if it were possible. I'm prevented by the same things as everyone else. So this outing - I really hope this opens doors, that I meet other sisters, find other venues. Here in N. Wisconsin it is limited.
xoxo,
Dani
@danikiss22 I'm with you sister! I'd love to be full time right now too. Unfortunately, life gets in the way of living. Hopefully soon.......
@danikiss22 Don't count on maybe when in shoes that could hurt. One thing that I have learned is that we have to look after our feet first. My two feet are different. One big toe is straight, the other bends in a bit. Guess which one hurts when wearing women's shoes.
There are single sleeves that can fit over one toe; there are silicone covers that fit over four or all toes; we can use tape, and so on. Shoe stretchers are important for those of us with wide feet. Just don't blow apart good shoes.
You could also use a broom handle tip to spot check sore spots. I use a small, wet paper towel pad to add a bit of stretch without getting the whole shoe wet.
@pipertime Yes. Whatever it is you feel like at the time, do that. However, do not let yourself get bogged down in picking the 'perfect' outfit.
Whatever makes you feel good looking in the mirror will do just fine! Now get out there and have fun! 🙂
Good luck on your planned trip out, as I have only been out as Samantha a couple of times the only advice I can give is wear shoes or boots that you feel comfortable wearing and can actually walk in.
😀
@samanthaj Haha, I was just about to say the same thing!
Of the few times I have been out, I made the mistake of wearing very high stilettos on one occasion and regretted the decision as it made me feel very conspicuously tall, I had to really concentrate on walking and they were at least half a size too small.
After that I went for slightly lower, slightly chunkier heels, which helped add a little more confidence to my walking, and a few less metres to my height.
@caroline2k I have a pair of black suede 4 inch heeled stilettos which I am happy walking around the house in but no way I would wear them outside, however I lovely pair of knee length boots with a 2 inch heel which I have wore when I was out and about and they are sooooooo comfy I can wear them for hours.
xx
@samanthaj Exactly! 🙂
Admittedly, the stilettos were a very long time ago and I hadn't put in the hours in heels that I have now, but I'd still think twice. I can wear 4.5" heels all day these days around the house, but doubt I'd fare so well on uneven concrete or cobbles 🙂
Mind you, I'd still not go for less than 3" in the heel 😉
@caroline2k That's an impressive heel height. For everyday I wear a 2-2.5" heel which keeps me at about 6'4". I'm fine walking in them, but conscious of height and surface underfoot.
I had a nice walk round a village in Devon yesterday. I wasn't aware of being stared at.
Anna xx
I had a nice walk round a village in Devon yesterday. I wasn't aware of being stared at.
The bigger problem is in our own heads. We are not-conforming to 'normal' societal roles, so obviously, everyone must be watching and criticising.
I admire your ability to just go for it Anna 🙂
@caroline2k I wouldn't dare do this near home. I did have to look busy on my phone when a couple with their dog walked past, but it is getting a little bit easier each time.
@annaredhead Haha, so it's not just me then?! 😀
Last time I went out in full femme-mode was in Leeds. I'm just too chicken to do it near home.
@caroline2k I had to rush past my neighbour on Friday, told her I was late and apologised for not stopping to chat. Hopefully she didn't spot the nail polish or makeup. I had a loose top, trousers and trainers on over my outfit. I drove out to a layby, made a few adjustments, put my wig on and then out for the day. Going through the toll booths to get into Devon I was lucky to get an attendant I didn't recognise.
Leeds sounds amazing
@caroline2k I like to describe your being “too chicken” as having common sense Caroline🥰
That has to be heels, lol
Sarah has summed it all up nicely, however you seem determined to wear some sort of skyscraper heel. If you are trying to attract attention, this is the way to do it as even GGs will get attention from everyone if they go out in stilettos. If you are trying to slot in under the radar and this is your first outing, I strongly suggest your footwear is conservative.
Becca
@rebeccabaxter continuing the conservative thing, wear a skirt or dress if you must, but I've been out and about almost exclusively in jeans (got some nice Sophia Vergara jeans from Walmart online, for only about $20!). Wig, red lipstick, hoop earrings (you can get little clip-on adapters), colorful windbreaker, muted top, jeans and flats, colored nails-I feel like I'm passing the "first glance" test-nobody's out scrutinizing for men in women's clothing (even though we all initially feel like they are LOL), so, if they see what they expect to see at first glance, they're not going to "drill down"... con-ser-va-tive. Win small victories, build confidence, lose inhibitions...then there'll be more adventures down the road that you can ramp up to! Good luck! 
@kendra2001 Exactly! We shouldn't expect to jump over the higher hurdles if we haven't practiced jumping over the lower ones first.
Is it gradualism? You bet.
If you go out during the day, wear sunglasses. The eyes show nervousness very easily. And make sure to wear comfortable shoes.
Not sure where your going nor do I have any good advice due to I never been out but definitely agree with the lady’s here confidence is probably your number one and depending on where I say I would try to blend to the community unless you looking for some eye attention then go all out 🤭
Your post says you don’t want to stand out so I would go with the jeans and a nice top. A woman wearing a dress is not usual in today’s laid back lifestyles. Fiona’s suggestion of sunglasses is a must as well. Keep it conservative and you should blend right in. Then you’ll feel more confident pushing the envelope if the mood strikes.
GP
