thanks everbody for your replies :D
actually the topic is a bit particular i think. i can assure you that all the fashion experts i've contacted told me to go for it, while all the people i've asked that are not related with fashion were divided in their opinions, some said yes (mostly girls), some said no (both girls and boys)
I totally agree with ruru and allan that is going to be tough, but still i consider that this kind of footwear was inspired for men during the renaissance and today is almost "prohibited" for men. Could it be because men simply didn't use to wear them anymore??? and only for this reason?? as most of you know Givenchy launched a thigh boot trend for men but these boots were not what i'm talking about and his style is more an haute couture style than an everyday dresscode.. like what Chester posted, and i agree it's not so goodlooking but it's because of the whole outfit and personal style of that guy.
Devin's point of view is interesting because of the contrast and that's what my question is based on basically. when women started wearing otk boots it was like crossdressing but then this trend became universal and accepted. maybe if someone has the right styling and achieves a good combination in his look can indeed pull them off and, why not, make others think about it positively...
by the way, this is what i have in mind would look like more or less(found on the web), even though the boots i posted would look way better!
(in the middle pic it's a guy wearing those boots, i bet you cannot tell the difference! isn't it unisex then?)