There's a real problem here that comes down to the status-quo of the office. Imagine your office of 100 people is 50% male/female, and a nice sampling of racial

There's a real problem here that comes down to the status-quo of the office. Imagine your office of 100 people is 50% male/female, and a nice sampling of racial groups, sexualities and ages (I've had the fortune to work in such a place). What happens is that there is sufficient diversity and commonality between enough people of their varying interests, looks and views, that you find it completely unnecessary to make comments about what someone is wearing, or whether their gender deems them capable. I say again, the problem with the high-tech industry is there is simply not enough diversity. Now we can't fix this today or tomorrow, maybe not in 10 years, but you can certainly imagine that it's there. With any comment, consider what is appropriate given a hypothetical situation where there is a good balance of whatever-stereotype-you-are-addressing and go from there.