Christ Chris 2220 posts.
I'm glad you found this place Kris. I wanted to chime in on something Eryk said. Confidence is a huge part of it. I mean, seriously, it's everything. If you feel guilty or ashamed or out of place, it's obvious, and things won't go right.
The feminized haircut thing stands out to me. I remember when I had my hair styled and highlighted for the first time, it took like 2 hours, spent the whole while gabbing back and forth, and she still offered to give me 'manly swoop bangs' if i wanted to go that way. Real sweet lady though.
For my last couple of cuts I've gone to a different stylist because she put long fingernails + womens' dress shirt + boots together with my long hair and went out of her way to try to do feminine touches to the cut. I appreciate that.
Next time I get my hair cut I'm just going to flat out say that I want her to cut my hair like a girl's, and I'll probably be bringing in some pictures for ideas

. As I said, confidence!
I was idly shopping for jeans at the mall the other day (discovered a new cut, curvy, it's high in the back so you don't show off your asscrack when you bend over. Must pursue this style) and a 17 year old girl I work with walked by. 'What are you doing here?' 'Shopping for pants.' 'You know this is the womens' department right' 'Yes, I'm a 2 petite.' "Oh.' and she glared at me jealously.

God, I remember the first time I shaved my arms... I wore long sleeve shirts until it grew out some. And my chest... same. I was so afraid of my mom freaking out. Seems so long ago.
But anyway, yeah, confidence. Women can pretty much shop for anything they want (since a lot of women dress their men anyway) so you shouldn't have any issues shopping for clothing. Try mens' underwear if you haven't already, it's a lot rougher, thicker, and wholly unpleasant compared to panties. You'll probably love it. Also you can probably switch to mens' shoes. Tennis shoes, no one will be able to tell a difference without being an expert.
Oh, you're probably a little young to want slacks for casual wear, but mens' slacks are a lot baggier than womens'. I love the way womens' slacks are, but there's NO POCKET ROOM. My mens' slacks pockets go down nearly to my bleedin' knees. You can fit a gun or a knife or something equally masculine (

) in each pocket, along with a wallet, cell phone, and a magic 8 ball.