People (especially the other women at work) knew something was up (but my coworkers knew already in 1999, when I came clean to my boss, and they were informed [my female coworkers were as good as gold to me - they took it upon themselves to be my very own support system!!]), but weren't absolutely sure what was going on. At the time, women's jeans had higher waistlines than men's jeans, so to avoid raising too many eyebrows, I wore my tops & tees un-tucked in my pants. This helped hide the waistline. I also avoided wearing V-neck tops at work (guys typically do not wear v-neck tops [at least not with as much of a V in the neck cutout as women't tops can have]), and stuck with your typical crew neck tees and tops. The V-necks were kept away from work, and worn outside of work (my favorite tees to this day are V-necks).
Shoe-wise, I was required to wear steel toes. I wore (and still wear to this day), lady's steel toes (sorry Jenny [one of my current coworkers], I know you've occasionally bought guy's steel toes for work [and have suggested it to me, when I have have a hard time finding the lady's steel toes I want in a 12B], but it's a philosophy/mindset thing with me). I've always preferred the athletic style steel toes, and you can get lady's athletic style steel toes in my lady's shoe size (12B), in pretty neutral colors, so that's what I wore. Of course by the time I needed to get them (my guy's steel toes were wearing out, and I was beyond the point of hating to wear them), and was able to get them from the shoe mobile (at an employee discount, which was great, due to money being tight for me at the time) that occasionally made stops at work, everybody already knew I was transitioning, so it was even less of a big deal for me to wear lady's steel toes.
In short, try to keep things as neutral looking as you can. They can assume by looking at you, that you're wearing guy's clothes, when you know that you're actually wearing women's clothes. When the rest of the company (outside of HR and the Quality Assurance department) found out what was going on with me, they asked me what I was going to wear to work for clothes. When I told them that I had been wearing women's jeans and tees to work for the past year or so, some them were quite surprised!
Tatiana, your OP/question was actually bought up in a group therapy session I went to in 2001, for the gender program I was in for my transition. At that group session (which was one of the last I attended [got sick of coughing up $75, to do nothing but listen to others oftentimes do the "woe is me" thing, while I said nothing, due to not having anything to moan about] - I went to them because I felt I was obligated to do so), the question was brought up about what to wear in the workplace. I mentioned what I mentioned in my previous post, and the moderator (who was one of the gender program's therapists) mentioned that that was a good idea/approach to take. Still, be VERY careful. Get too femme looking, and eyebrows might be raised, and questions asked before you're ready to come out about your transition.
