Ironically, I think there's something so feminine about wearing men's clothing or clothing inspired by menswear. I'm really not a tomboy at all (although I do know how to handle myself at the shooting range) and of course, wearing clothes meant for the guys requires careful balance. Skinny jeans under the slouchy sweater, gold studs in your ears, some delicate shoes. Something feminine to offset the masculine and provide that delicious and confident contrast. (Because getting mistaken for a boy is not the goal here!)
I would compare this to my love for old against new. Contrast is everything when it comes to style. Aged wooden furniture paired with the most dainty, white porcelain china. Boxy, masculine oxfords with a flouncy dress. Bright white walls and a worn, cognac leather chair. A loose white tee tucked into fitted black pants. It's the layering, the mixing, the balancing act--you could even say the contradiction--that makes these pairings so chic.
Do you or would you wear men's clothing? Do you agree that menswear can be (counterintuitively) quite feminine? I'd love to hear!