I'm just going to say that this is based off things you've posted, so I may be way off, but it doesn't sound like you've had a lot of experience with relationships, and work relationships require finesse to handle even if they are good, or even more to handle if they go ugly, really ugly. When you date someone at work, even if it is the most perfect relationship ever you are going to have to deal with your coworkers making comments and everyone being all up in your business. I don't know if you're as open at work about yourself as you are online, but you may work with people who will use it against you. Why not just attempt a friendship with this guy as it seems you have common interests and if it becomes more than friends with common interests look at the situation then.
On to your work attire:
I find it odd that you work in a public library as a youth librarian and they made an issue of socks and Mary Janes. Most public libraries and library staff I've seen really rock whimsical stuff hardcore because of the kid factor. It isn't the way I'd dress, but it always felt like that was one of the only acceptable places to wear vests and sweaters with cats on them or earrings and socks with a shape or design. If you were a plain old reference librarian it wouldn't even be that odd, but a youth librarian it is the norm for a lot of places. One of my bosses is totally awesome, but wears socks with Teva rafting sandals and it makes me super sad
Maybe you need to write Library Journal to the column on work place issues and they have people write in with their analysis. Just don't wear farm animal toe socks with Birkenstocks (I've seen this before
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