Wow, I'm surprised more people haven't commented on this thread! Androgyny or cross-presentation often means no job I agree, but it doesn't have too necessarily....
I agree that hairstyles need to match the environment one is working in, therefore if its catering - hair needs to be neatly arranged away from the neck, face and the food you are serving. Same if you were working close to moving machinery (as your hair could get caught). However, people should have more freedom over exactly HOW they wish to style and control their hair. And not simply have to conform to gender stereotypes.
Natkat - As for job interview - I do feel its best to dress in the gender in which you pass. This may be a heartbreaking affair for some, however, ultimately we are bound by society and current ways-of-thinking. If you really want the job, try whatever you can to get it. Then, when you have worked there for a while, are secure, are working well, know your colleagues well, and have formed friendships or great working-relationships with bosses and HR (very crucial!), then you may be able to start presenting as how you wish. If you felt uncomfortable around a potential employee, would you hire them? Probably not. And that's what you have to think about first and foremost. Not all transphobia, is actually transphobia I should imagine. Its just average guys and girls simply wanting not to make faux pas or have their job made harder.
As for clothing (and hairstyles included) if you are going to present more towards your target gender, as opposed to your biological sex - then its best to provide subtle clues as to how you wish to be addressed and customers and those you work with. Alot of hostility towards transpeople at work is perhaps simply because the other people you work with may not know what YOU wish to be seen as, and therefore feel embarrassed that they'll gender you wrongly and look stupid as a result. Basically, as a cross-presenting person, you increase the risk of others' making faux pas. And their worry that they'll misgender you can make people angry towards you as they'll look stupid or bigoted. Also, if YOU are nervous about your presentation, others will be too, and will pick up on that - with obvious negative results.
So as an MTF, if you're going to dress feminine or as a female, perhaps try to be as warm, talkative and approachable as possible. AND make it clear how you wish to be seen and addressed, do not assume that the other people will automatically know, as they probably won't. Guide the people, especially those who are just unsure, potentially bigoted or just benignly ignorant. Make them feel at ease, and there's more incentive for them to make you feel at ease. The more subtle clues and almost-subconscious assurance you give them, the less likely they'll feel put on-the-spot, and the less opportunity you give them for misgendering you (purposely or otherwise). Also, I think its wise to tailor your presentation to the situation and environment you are in. You'll have more latitude and freedom with in certain environments than you would get within other environments, and that's just the way it is and will probably be till the end of time and the day-after.
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As an example (though I'm not a binary person by nature) - I dress with feminine clothes to work, and often a subtle feminine hairstyle (hair in a neat up-do for instance). Technically, I'm blatantly crossdressing - its obvious my clothes are for females due to their cut, buttons on opposing sides, colours, texture, styles etc. My silhouette is very feminine, however up-close I am obviously male as I don't wear make-up (though I close-shave and neaten my eyebrows, etc). There is usually some slight pause, sign of confusion (or potential "I bet he's gay!" bemusement) when customers or colleagues see me for the first time (or when I have a new outfit). So I make sure not to get into any mutually embarrassing situations by immediately speaking in my male voice, using masculine mannerisms and such, to put them at ease. Then, when we've gotten to know each other, and they don't feel confused or threatened by my unusual presence - I'll be able to have more freedom in how I act. Its a bit like social gearing :p Don't go into work in female clothes in top gear as people will freak-out. Don't go into reverse, but do go slow.
Therefore in most cases, I'll get some disapproving and confused looks at first, but then as they get to know me, and I act in a way that they find familiar - they simply relax and don't notice me after a time.
If I took HRT and began to look female, I'd act male around around everyone who I knew before the effects started. And (if I passed as female) I'd be more openly female around those who I had just met who automatically assumed I'd be female, however if asked, I'd subtly convey that I wasn't cis female. Once again, I'd tailor my response to every individual situation, in the same way most people slightly alter their mannerisms when they are in the company of a boss, friends or family. Its not a fool-proof or 100% effective system of course, but its definitely more advantageous than having a blanket approach to presentation in social situations.
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Presentation at work is something which always was an issue for me! I worked in catering for many years, various restaurants and hotels, and found it highly problematic due to my hair and build. The uniforms were always too big and boxy (which meant i genuinely looked terrible shabby and baggy), and of course long hair (even when tied, was always viewed with suspicion). I used to hate wearing ponytails as I've never liked the idea of being a guy with a ponytail, as it just looks too grungy and male. But then it clicked, and I thought "so why don't I just tie-it back in a feminine style, duh! Screw them!", and so I did. It was both hygenic and pretty. But of course, male waiters aren't meant to have pretty and neat hairstyles, so the bosses didn't like that either. Haha. I carried on doing it anyway as I worked very well, and they knew it.
