How do I know what size I should be buying? should i go by the waist size or the chest/bust size? If I go by waist size then its too tight up top but going by chest size then there is too much fabric by the waist. How do I find the happy medium? are there any types of dresses that look better on a male bodied person? also still not dressing publicly female so cant really go and try one on pretty much just guess and order something online. the couple that I have ordered dont fit well at all but that could just be that they are cheap dresses too.

I have a thin-male's body, and typical male shoulders.   I find that, for dresses and tops, I buy what fits my shoulders.   I look for dresses with a natural flare at the waist to give the impression of hips even if there aren't any.  I had a few "A-Line" dresses (I think that's the term), where the waist line is higher, just below the bra, flaring out below that.   I thought those to be the most flattering to my lack of figure - haven't seen any for a while.

Questioning, Probably one of the toughest things to find the right fit for us girls is dresses. Most of us have broader chest and shoulders in relation to waist and hips than most cis-girls. Pick your dress size by your chest/bust measurement. Your dress really needs to fit proper through your chest to look good. If there is a lot of bagginess in the waist you can have the dress taken in through the waist. If your very slim in the hips , dresses in the "Fit and Flare" style will help your hips to appear bigger than they really are. Peplum style dresses also do this. Also keep I'm mind if your a tall girl you want to stay away from vertical stripes. Another tip bigger patterns usually look good on bigger girls, small patterns on smaller girls.Another tip skirts and blouses. You can buy the skirt to best fit your waist and hips your top to fit chest and shoulders. It also allows mix and match. More bang for your buck so to speak.Also size and fit can vary between brands so always check the size charts when shopping online. Don't worry you'll get the hang of it.

there are a couple online websites that tell you what your dress size is. You just plug in all the numbers like  chest , waist , hips etc. and it gives you the dress size.

the dress I am wearing in my picture is tight about 5 inches bellow my breasts then loose. it goes a long way to hiding the stomach fat and lack of curves. I would say I love that dress and thats why I wear it so often, but the simple truth is I do love it...I also don't have enough cloths to not wear things like every week.

I had help picking it out the first one I tried was actually too big not something I normally experiance, glad I had a friend, it was easily the most relaxed shopping I ever did.

Serena

So many different ways to go about it... really, the best way is to try them on. Second would be to read reviews on prospective dresses. See how people described the fit and the elasticity of the material.

With non elastic fabric, fit your chest. If waist or hips are loose, then have it taken in some (or pad).

Slightly elastic, split the difference in the waist and chest difference.

Dresses with a flared skirt give the illusion of hips. You can also see where the waist sits... low or high.

Bodycon dresses will show any lack of hips immediately. Pads work wonders and are gold.

And the list goes on and on and on...

Walk into a store and ask a salelady for help. Its so michevious and fun but I just love doing that and they will gladly help - they may blush a little. I dress androgenously normally and try to look more male because of work and I sometime get the look from ladies in the changing room ....just smile.

I've tried fitting for everythingthing - bras are difficult to fit but now I know my size with the salelady help. I just bought a "push up" jean and omg they are so good..Dresses may be difficult if they are a tailored fit but loose dresses are less demanding. Otherwise go on line there are so many options there and you may make a size mistake so be sure you can return the item.

I found that going to the thrift store and buying everything on sale (some are a dollar each)
then sort it out at home

its a bit wasteful I guess, and I redonate the nonfits...but I learned that sizing is all over the place

I made a mental note of brands and sizes so now when thrifting, I have a very good idea what will work

but I have also learned its ok to just go in the fitting room and try them

buying new and online ended up costing me too much and most things did not fit, esp shoes

Now you know why women spend so much on clothes!  Most women have things in the closet that still have tags on them.  First, while I love the look of dresses, they don't work on me.  Misses sizes are meant for women 5'6" and shorter.  At least until you reach the petite sizes for really short women.  Now, there are stores that specialize or have special lines for taller girls.  They tend to have more distance between the waist and the bust.  Look at the j.Jill line or do a search for tall girl fashions.  Michell Obama is 5'11" and I know that she wears j jill sometimes.
Another good option is to find well made things in larger sizes, then go to a good seamstress to take in or let out.  I have read many articles in the girls mags that tailoring is the secret to looking great. You also have to be aware of what can be altered, and these tend to be the more expensive brands.  It can be expensive, but a wardrobe maybe should have a mix of well fitting dresses, some classic separates, and sport type outfits.  I saw Caitlyn doing an interview the other day in a golfing outfit.  She looked pretty comfortable, and it looked like something she could do herself without 12 assistents doing the hair and makeup.   

If i were to get a dress, I would concentrate on the chest. I've had to return many cause i couldn't close it up top. As for styles, I would get something that either is a body con or something that fits the chest area and flows over the rest. But since I do have a hard time with dresses, I just mix and match tops with skirts.

I know his sounds so terrifying, but as warlockmaker said, go into a dress shop and ask. In any major city the sales assistants really don't care, they want to make a sale. Even tell them you are TG and just starting out and are very nervous. You will likely be overwhelmed with help.

I got my bra fitting that way, and instruction on how to adjust it and advice on styles. Dresses were the same.

Nowadays it is just natural of course as I'm fully transitioned, but I do take newbies to clothes stores to help them out and not a single one has been in anyway insulted or laughed at. They usually get a discount.

The last new girl I took I told the assistant that I was buying the dress as my friend was broke but needed her first dress. She got it for free and was told to come back at anytime and not to be nervous.

If I go by most of the classic sizing charts I should be a 12 or a 14 (USA). Which years ago was mostly true. I do/did tended to have a bigger bootie so that accounted for some of the variabilty, plus being 6ft tall doesn't help. Thanks to today's vanity sizing I am mostly a size 10, sometimes an 8 and pretty much nothing dimensionally changed besides loosing a little of the extra padding on my bottom.

I tend to favor thrift shops. They cater to my sense of frugality and have some amazing bargins. You can also find some great end of season sales in retail stores. In retail stores back in the days of "guy mode" shopping, I'd find what I wanted in the womens section and then as I head to the men's changing area grab a pair of jumbo size trousers as a sort of cover for the armfull of clothes underneath. Worked every time. Just avoid the shops that have the clothes counting custodian in the corridor

You can always use a belt to take it in around the waist.