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What kind of pretty/feminine stuff could a man wear (and get away with), if he's not making any attempt to pass as a woman? I understand if you folks don't think it quite fits this board since I'm not trying to pass, but it's still a sort of covert crossdressing, so hopefully it fits.
Specifically I'm asking about tall flat-heeled boots like these, but I'm curious about other stuff too, like various kinds of hats, maybe necklaces or other jewlery, etc. And in what settings could these things be gotten away with? I never see them on men at the office (not even the sloppy-dressing ones on casual friday) so I'm guessing not in a business setting.
(In case it's not clear, "these" boots are in the link at http://media.photobucket.com/image/megurine%20luka%20boots%20cosplay/itsukifujii/VOC10Shoe3p.jpg -- not used to text-based imageboards, I guess).
That depends on your definition of normal.
If you don't want to get noticed, you should stay away from things like this if you don't pass. (I'd stay faar away from those boots even once I do pass! =P)
If you don't mind getting noticed then it really doesn't matter. No one's going to say/do anything.
There are a lot of so-called gender neutral clothing items you can option: sweaters, layered camisoles or tanks, slim jeans, button-up shirts, even capris. I have them all in my closet, and wear them all with relative frequency.
Shoes are more difficult, mostly because mens' feet are usually two or two and a half sizes larger than womens' shoes. But if you want boots, personally, I love boots with a block heel... I have a black, leather, lace-up pair that are the perfect blend of cute/sexy/functional. If you know where to search, try searching by heel height; it may work better than sifting through pages of online stores where all of their sexy boots have five-inch heels.
Yeah, the shiny gold part is way too gaudy, I was actually thinking more of a brown. :P
But without getting into it too much, it would definitely be pretty out of the norm for me I guess, so maybe I'll just skip it. Meh, I'd probably be wracked with anxiety just owning it, haha.