I guess it depends on what your goal is. Based on your description I'm assuming you have no interest in being in the closet with your clothing adventures. If you are hoping for a masculine look, then there are certainly options, but I think you would need to think about ensembles that work, rather than just throwing anything on. The two looks that I can think of that go with male hairy legs are indian/hippy/surfer dude look of varying length lunghi wrap/skirt with flip-flops/sandals, or the fairly plain styled knee length skirt with chunky biker boots.

Personally I like the guy in a skirt look for myself, and it is the main (only?) CDing option that I use at home at the moment (also less likely to freak out the rest of the family). However, my aim is a feminine look, without looking ridiculous (IMO). So for example I have smooth legs and wear sheer stockings, ladies flat court shoes and a denim mini skirt. So I look approximately female from the waist down, and like a middle aged balding guy from the waist up (Hmmm! charming image :D- I'm sure it looks slightly better than it sounds - find my picture post if you want)

Anyway, I'm guessing that's not the look you're aiming for.

As mentioned, I think the problem with the masculine look is the limited combos that work. There are very few skirt styles that would work with hairy legs, and the clash of skirt with guy shoes and socks certainly looks wrong to me when I've tried and looked in the mirror (I was vaguely considering if there was a look I could use at work, and that wasn't it!). With smooth lightly tanned legs, I think a shortish skirt with running shoes/trainers and no socks/trainer socks could work. Again, the combo could be more feminine than you're after though.

You could consider checking out posts by JiveTurkeyOnRye (hope you don't mind the plug) on this site for a stylish take on dude-in-a-skirt .

Susie