Again, I will caution you very strongly about going anywhere in public wearing girl’s clothes.
You might want to read some of the answers on This Thread about a 14 year old boy wanting to wear girl’s clothing.
You also might want to read This Thread about Gender just so you can see what you might be up against.
And you should especially read this other thread About sons being allowed to wear dresses. You would not believe the raging debate about this subject. Even some of the Flutherers made horrible comments about the idea of boys wearing dresses. But you should have a look at these threads, because even though we are a microcosm (and a pretty liberal leaning microcosm at that) you need to be aware of what can or might happen to you if you wear dresses. It’s very sad, that as a male, you can’t just simply walk out of your house with a dress the same way a girl can walk out of the house in a pair of pants, but this is our current reality and you need to be extremely aware of these facts.
So read the threads and then we can start talking more about what you might like to try wearing.
Of course Levi’s 501 jeans, a T-shirt and a flannel jacket are pretty common place for both boys and girls, with a pair of Converse All Star low-top tennis shoes or desert boots, or wallabies or Sperry top siders (in leather or canvas) or Vans tennis shoes which come in every color of the rainbow. Just about any kind of walking shoes like these would be good too. These Chinese-style shoes come in both slip ons and Mary Jane styles and go with both pants and skirts. These canvas shoes are pretty cute and unisex too. Of course, there is always Keds which also come in every color of the rainbow (the women’s shoes have a pointier toe, like the ones in this picture).
Here’s a picture of a girl that might help you.
And here’s a grunge-lite look for girls.
This photo has 2 good examples of cute, not too feminine girls outfits (look at the 2 on the left, the one on the right is a bit much, unless she had tights instead of lacey underwear).
Here are some examples of skirts that are made for guys I’ve seen guys wearing these to Emo/Goth/Punk concerts and because they were in like company, no one really gave them any grief. They’re often paired with a hoodie that is tied around the waist, which also kind of resembles a skirt.
If you want to try something a little bit more feminine (and do be careful where you decide to wear something like this in public) this is pretty without being too flamboyant. Or these skirts or This look
The next examples are pretty much unisex looks that will work on boys or girls. Check out this look or These outfits (minus the high heels) Cargo Pants are always a good unisex choice. Capris-length pants can also be a good choice.
Of course a good jean jacket will go with just about everything. Or you might want to get a pair of denim overalls (both long and shorts style)
And a good pea coat is very versatile. And courderoy pants.
Let me know what you think, especially after you’ve read the threads from above. : )