Up until now i have worn Androgynous looking men's clothes and i have only just started adapting to female cosmetics (just womans deodorant and moisturiser at this stage) and androgynous  looking woman's shoes i am still quite hesitant to wear anything that would be obviously feminine at this stage. however an opportunity for me to "Cross Dress" without causing any suspicion and providing an easy entry point has just presented itself.
however it is less than a week away and i do not have any clothing at this stage and only a very limited budget to work with.
items i have considered include: A Black Skirt (probably essential in order to look like I'm cross-dressing rather than wearing my usual androgynous clothes; Heavy Black Pantyhose; and i may need some sort of underwear as my boxer shorts are likely to be too cumbersome; i also like the idea of getting some Dark Red nail polish.
this would have to be worked in somehow with an existing shirt or V neck T-shirt and either a hoodie jacket or a leather jacket (both existing) but I'm uncertain if i can acquire all these items in the next week.

so what items should be highest priority

Ps: I have decided not to use make-up as it is expensive and i have no experience using it so for the time being make-up is completely out of the question.

I'm also uncertain as to where this should be posted as i feel it covers multiple categories

Basic makeup items do not need to be expensive.
I usually clean my face with toner and cotton. ~$3
Then apply moisturizer or essence. ~$20
In summer, shisado sun cream~$50
Finally, foundation for occasional outing ~$30
Sometimes I finish with powder ~$10
Mascara ~$10
Lip gross ~$10

Barbie~~

Well thank you
i will try my best and see what i can do with what's available.
i had thought of adapting to very minimalist make-up while still presenting androgynous so as to ease the shock factor and get some practice before putting it all together at a later stage   

Makeup application is a skilled craft not unlike drawing or painting and takes a good deal of experience to do well. It's really best to get very good at it before displaying your handiwork in public. I suggest setting a regular time of the day/week just to practice, but not go out in public with it. Eventually, you'll be good enough at it you can confidently go out. In almost all situations, less is more with this stuff, especially when doing an andro thing.

A good way to accelerate the learning curve is to spend some quality time with a friend who's good at it and willing to give you some tips. Otherwise, YouTube is chock full of makeup tips. My fav is a lady called leighannsays.

~ Lyric ~

Quotei do not have any clothing at this stage and only a very limited budget to work with.
items i have considered include: A Black Skirt (probably essential in order to look like I'm cross-dressing rather than wearing my usual androgynous clothes; Heavy Black Pantyhose; and i may need some sort of underwear as my boxer shorts are likely to be too cumbersome; i also like the idea of getting some Dark Red nail polish.

So the items you are considering are:

Black skirt
heavy black pantyhose
underwear
dark red nail polish

Prior to thinking on this...note there is one "cosmetic" item, the red nail polish. That goes for about $6 US for Sally Hansen, which is a great quality. You may also want to buy a clear coat, also SH, also about $6. Clear coat (when used as a base) protects the nails from becoming stained (important if you don't want evidence to remain on Monday), and when used as a top coat really makes the color POP out in all its vividness. (It's ok to use it for both top and bottom; in fact, you're supposed to do at least 4 coats--bottom coat (clear) + first coat (color) + second coat (color) + top coat (clear), allowing it to dry between all coats.

I'd suggest choosing that, just to get the "odd one out" from the equation.

Cost is a definite limiting factor...ok, the process of deciding should start with:

What is the single most effective clothing item of the 3 listed?

Skirt, pantyhose, underwear?

Definitely need something to tuck The Boys away, otherwise you'll have an unsightly bulge where women don't...can you say "clocked!"

Underwear is cheap, find it for $7 US at Wal-Mart. Get the cotton kind, I prefer the "bikini" style but others like different styles...but cotton is important. Get one size too small, and wear two pairs to help with tucking.

Pantyhose by itself is useless, so that's a last choice...I'm not sure on the price, but iirc "body shaper" hose is about $4 US at W-M.

That leaves the black skirt...which you can wear without the pantyhose if you money pit has run dry.

So, panties to hide The Boys (very effective at feminizing...or rather, not masculinizing), first choice.

Skirt, goes well with shirt (or V-neck blouse, found at thrift stores for $5 US if money is there), very good for feminizing, second choice.

(Blouse from thrift store = 3rd choice, much better than a guy-shirt or T-shirt, which reduces the "classy lady" look by -25.3 points imho)

Pantyhose = fourth choice

Have a great time! Good luck with your process!

Quote from: BD0121 on May 05, 2013, 03:56:42 AM
Well thank you
i had thought of adapting to very minimalist make-up while still presenting androgynous so as to ease the shock factor and get some practice before putting it all together at a later stage   

In my experience, the most shocking factor was wearing skirt. Others are just fine. For example, painting nails or wearing makeup can look weird at first, but usually OK to most people. And people will be accustomed to it soon. For facial makeup, the most shocking one was my wearing red lipstick, but it was still OK for most of my colleagues.

barbie~~

OK so I've decided that I will probably pass up this opportunity and put off my first public dressing experience for a few weeks this should give me some time to acquire at lest a full outfit and some basic make-up but advice is always appreciated.
thank you people   

Just don't make the mistake of waiting until you no longer have the freedom and opportunity.  You'll regret it!

With regards to logistical matters lots of people have given examples of items and prices from the United States
I live in Auckland, New Zealand so some things are a little bit different
Op shops (thrift stores) tend to be quite pricey so unless you are looking for formal clothing it is usually a better idea to go to one of the mainstream clothing shops.
as far as size is concerned i am smaller than average as a boy so i tend to fit cis woman's clothing especially if I thinned down a little.
i know there are other problems with my above statement but i can't be bothered dealing with every last detail at the moment

What we Americans call "thrift shops" are stores that sell used clothes, generally in good condition, gathered from people who want to get rid of grandma and/or grandpa's clothes after they no longer need them (either from death, or downsizing prior to moving into a senior home).

Also, often "better neighborhoods" have wealthy people who buy the latest clothes late in the week, but by next week they don't dare be seen wearing the SAME thing as last week...so one can find current styles...you just gotta get in early to grab it.

Try on everything, and don't be afraid to learn basic tailoring techniques! We former males have broad shoulders but narrow hips (or other non-femme body types) and could use a little help in the fit and finish dept.

Buy large, and tailor to fit. Google always has currency conversion tables, just search for US dollar to  AUS dollar"

i'm going to head to the shops to see what I can acquire and from there i can deicide to either wear it on Friday (if it is complete) or at my next opportunity on Wednesday the 22nd.
i don't have to look that good as the idea for Friday is to dress in shocking clothing anyway.
the reason i have chosen these day is that i can justify looking like a man in drag so it felt like a good starting point however i do intend to do my best and eventually start dressing well. that however will take time and money.

Ok i now have half the items needed;
i couldn't however find a skirt today but i will keep looking;
Blouse cost $2NZ (on sale from $8NZ)  at the Salvation Army Shop so that was my best buy.
i also brought some liquid foundation my most expensive product at $17NZ

Update:
Eyeliner and Nail Polish $5ea although both look very hard to apply 

Quote from: Comrade Eva on May 07, 2013, 11:29:25 PM

Eyeliner and Nail Polish $5ea although both look very hard to apply 

practice
practice
practice

well i have all my clothes for tomorrow night
It doesn't look very good but it's a start.
but the shopping experience was worthwhile and everything fits me.
no jacket however! 

here is an image;

So i now have 10 hours to put it all together for tonight.
the event itself is a Protest against Homophobia in the workplace. my friends might be a little surprised but they can hardly be nasty to me when you take the context into account.
I'm surprisingly  quite relaxed although i might get later on.
regardless i have decided that i will go out in public dressed as a women Tonight (it also happens to be my 24th Birthday today {it's the 10th already in NZ}).
thank you everyone for your advice and support!

Well it's done
Six hours in public dressed as a woman
Everything went well and my friends were very supportive.

Defiantly lots of fun and i can't wait to do it again!

and just as a footnote: i have worn the red nail polish since that day without any negative reactions from anyone.

Now that I'm past the awkward beginning stage i was wondering where i should go from here. specifically what items of Makeup/Clothing should i try to acquire?
so far i have encountered no hostility but i have been very careful in public.

I would suggest you take a little time, look into yourself and think about what exactly you like about "cross dressing". What's different about it from the way you were dressing before? List the details on paper. Resort the list into an order according to what you like the most to the least. The top of the list is obviously a good place to begin.

Not everyone has the same interests and agenda regarding "cross dressing". Without knowing yours, it's hard to make suggestions. From everything you've said it almost sounds like you simply wish to experience being in "public dressed as a woman". You can do that without passing as a women to others. And you haven't indicted anything about your inner feelings about your gender, so you could just be playing a dress up game. Not that there's anything wrong with that.

Let us know.

~ Lyric ~