What to wear the first time going out dressed as a woman

This all comes down to how you are feeling in yourself. Do you feel that you are ready to show this side of yourself even if it is at a Halloween party?

Putting that aside, as for what to wear. Well seeing as it is a party and I'm guessing the intention (at least in part) is that you going as a woman is your outfit then you should really you sbould go dressed to the nines. The full works. Heels, hair, full makeup, gorgeous dress and even jewelry. But obviously you'd need to be comfortable dressed to that level.

Yeah I’m not 100% sure if I am ready. I just know I want to someday and I always put it off haha.

Yes, if I go out I do plan on getting makeup professionally done.

Thank you for your input, I appreciate it. 😘

The first time I ever went out fully fem was when I was 18 and went to a college Halloween Party. I was dressed super sexy, even slutty. I loved dressing like that and did it often but only at home. I figured this was Halloween though. It was my excuse, reason and cover to dress like that and go out.

It was scary and exciting being out like that, but I loved it. On the long walk from my car to the building, I didn't trip and fall in my stilettos. I got some looks but had no trouble. I loved the party, had a great time, met some other dressers and lots of admirers.

I had a girl help me pick out my outfit including my wig. She also did my makeup. So I had help.

What you wear depends on the look you want. You can be conservative and blend in or turn up the heat and dress to impress and get noticed. I would say wear what you like. Maybe when you get your makeup done, you can seek some professional advice on what you should wear and get it done all at once.

Look around and see if there is any crossdressing support services or meetup groups near you. Good luck and have fun. Do it tight and you will never forget the experience.

But, I’m going alone, because I don’t have any friends that are, gay, lesbian, trans or crossdressers.

Funny, did you consider you might have friends who think they don’t have any friends that are, gay, lesbian, trans or crossdressers.

I would err on the side of conservative to start, that way you will blend in more easily and avoid the teenage boys looking for "fun" by taunting you. Also if you aren't good in heels yet go for low, wide heels to avoid a broken ankle (and you can run better in them if needed).

Get professional make-up done and a wig fitting, 90% of passing is the face!

Biggest thing is to relax and smile, I've seen many CDs scowling away and it draws attention and underlines the masculine facial features. Go and enjoy, and don't be surprised when no-one notices!

S

Madi, halloween is the time of smudged eyeshadow and blood stained lipstick, wear anything black and don't take it too seriously.  Just carry a bucket filled with sweets and 'cackle' occasionaly to complete your disguise 🙂

Sal x

Madi,
Go for it. I agree with the others if you can get a makeover it will be a great thing to learn from but i would dress what ever makes you feel comfortable and make you smile. Makeup wig and a smile go a long ways and a little confident you will feel happy about going out. By going to a CD/gay club you will also feel you are not being singled out to make fun of most will not even take notice. You can also meet a few friends. Just be careful some guys go to those places for a pickup. Remember confidence and a smile go a long ways to making it easier and you more feminine looking.
Good luck honey.
Sara

At Halloween you can dress anyway you want. When not Halloween when I go out I dress conservatively, usually just a jean skirt and button down blouse with pumps or sandals.  Last afternoon I had to go to the Post Office and mail a letter so I put on a pair of women's shorts, white V-neck t-shirt and sandals. I did have basic makeup and a short wig on. I just had French nails done so they looked great. Under my t-shirt I had a white lace bra. I find that when dressed this way people really don't pay any attention to you at all. I try to dress just like the other women I see. What ever you decide to do, enjoy the evening.

I would go for the conservative look as well, and think about what you would be most comfortable in? It is a difficult and stressful thing to do, and by wearing edgy clothing, you'll only up your stress level.

Temper that with that it is Halloween, and the usual rules are different, but think about your comfort level.

Amy

The first time I kept it simple and did it at night to make it easier.  I wore matching underwear, forms, and a black dress.  I wore leather flats as I was worried about walking in my heels, and a fleece over the top.  I had a pair of sweat pants in case I chickened out.  I didn't wear makeup or a wig.

The second time I took it a step further adding stockings, garter belt, mini skirt, blouse, and I wore makeup and ladies flats.  Next time I will wear earings and a wig.  I was ready to do this the other night but I chickened out when the street got busy.

I don't think it's a big of a deal as we make it out to be in our own minds.  I don't think most people care or notice unless you really got out provocatively.

Best of luck!

As other ladies have said, it all depends on context.

When I went to a Halloween party, I pulled out all the stops - in for a penny, in for a pound, as they say.

When I went for a country walk by myself, I chose a floral dress, wig, coat - and wellies, since it was November in England.

For New year's eve, I wore the glitteriest suaciest gold dress and heels for celebrating in Trafalgar Square.

For shopping in Brighton, it was jeans and blouse, with a ladies suit jacket and trainers.

For clubbing - I went by myself, but Brighton is what I'd call a safe environment, and I'd been dressed all day - I chose glittery, sequined dresses with a big "Wow" factor, glittery makeup and blingy jewellery. And glitzy heels, naturally!

I had the time of my life each time I went clubbing like that - the dress practically invited people to talk to me by myself.

I'd say therefore, for clubbing, make as much effort as you can/dare, as it pays off. People like people who make an effort.

But you need to feel comfortable with it.

I'd spent all day dressed and wanted an upshot.

Going cold into the glam could be a shock!

Tone it down, by all means, and dress comfortably, but add some zing to show you're out for a good time!

Love Laura

Madi,

So many people have said it here: their biggest regret was not going out sooner! There is nothing like the feeling of a cool breeze under your skirt, your long hair flowing, the click of your heels and the jiggle of your breasts as you walk.

Go somewhere you won't be afraid to meet someone you know, relax, smile and go out and enjoy. A walk in a parkour something to start, then work up! Any funnily broad daylight is better than at night for blending in, a single woman at night is a target sadly in many places.

Hope you get the courage up!

S

Hi

My advice (from the UK)  would be to have a makeover (if that's a UK term, it means having a professional do your makeup), don't wear heels unless you are REALLY comfortable in them and wear clothes that any real female would wear who is about your age. That way you won't draw attention to yourself (from ordinary members of the public) and you can enjoy your time en femme.

Just my half penneth…. or should that be half cent.

Jean x