I have 3 pairs of flat oxfords at the moment - 2 pairs of Born Arlettas and the Boutique 9 laceless oxfords that several of us got last year. I definitely prefer the more feminine type of shoe like #1. My main reason though is that they look better with skirts/dresses which is not an option for you, but I think some of the same considerations apply to wearing them with skinnies. The more masculine type looks super long and skinny when a lot of the shoe is showing, like you've mentioned. To my mind, the main difference is how long the front part of the shoe (like from the end of the laced part to the toe) appears - a very long length here looks very manly to me, so I prefer something shorter in this area. A more delicate toe shape and brogue or other detailing also helps break up this region and makes it appear shorter.
ETA: Deborah's oxfords look much more feminine than the black/white ones that you showed, since they are more delicate/pointier and have details to break up the front, as do Angie's in her outfit today as well.
ETA2: FWIW, I think this is a bit of a poisoned eye thing for me, though, since i personally do not like the look of long, skinny shoes sticking out from under skinny pants. I don't like cons with skinnies either.