I've been experimenting with skinney jeans for a while now. They are slowly getting more and more fem looking the next last pair I bring was black but they looked more like ladies jeans than men's I'm hoping next to get a pink pair and slowly work up to getting more and more fem eventually leading up to a skirt or a dress. I don't know what the next step after pink skinney jeans is but welcome any ideas??
I agree with artiewhat. Something with a distinct feminine design. Animal print is a good start, but you could even consider multicolour or even floral prints. Next thing I'd suggest is feminine shoes. Doesn't have to be high heels, just more feminine shoes. Like women's trainers/sneakers, and work your way up from there, maybe switch to a women's boot. And then the shirts/blouses/jackets: Try to buy unisex/gender neutral clothing to start with, or maybe even buy a ladies jacket (doesn't have to be pink, but just a feminine cut/style). I don't know really, as I don't dress girly/overly feminine. Hopefully someone else can give you better advice. Good luck and have fun! (*hug*)
Women's t-shirts, feminine sweaters and jackets are usually cut differently from men's clothing you could try those. Maybe a pair of girls shoes, and some feminine accessories too.
More and more guys have been wearing floral prints, I think it's the new trend. Floral button-ups and tees are a popular and preppy style right now, as are floral canvas shoes.
I would recommend something bedazzled or with sequins. It seems like the intermediary your looking for. Or you could just dive in completely and start wearing miniskirts.