Ok, I don't post on this forum very often anymore but I checked it today and saw this thread and thought it was worth adding into. Anne, I go out as a man in a skirt on a frequent basis, several times a week in fact. I run the spectrum from guy in a kilt to actually wearing women's tops with skirts and tights and boots, and variations inbetween.

The most important thing you need to wear if you do this, is confidence. The first couple of times I went out in public in a skirt, I was scared of what I was doing, so I looked nervous, and intimidated, and because I put off an aura of "I'm doing something wrong" people noticed it and treated me accordingly. The experience was so nervewracking that it took me well over a year to do it again. When I did it again, I really took a good long look at myself in the mirror and said "I really look good like this," and then went out and have never looked back. I keep my head up high, I make eye contact with people, I smile, and I make sure to behave like I belong anywhere I go, and I have not had a single problem yet. Yes, people notice, they might give me an odd look, but then they move on. Occasionally people will make a comment, and I've heard teenagers snicker behind my back, but that's what teenagers do. I've passed loads of cops while walking and haven't been beaten up or even verbally harassed by them at all.

The comment someone else made about really taking a good look at yourself in the mirror is spot-on. The big pitfall of the man in skirt look, when one start to incorporate things like pantyhose and heels especially, is making the clothes work on a male body. I typically don't wear women's tops and dresses because they're usually cut to eccentuate breasts, so for a long time I really had an issue with having this look that seemed half and half, as in top half male bottom half female. The best solution to this is making sure your men's tops are as fitted as possible, a lot of guy clothes are a little too baggy, which doesn't work well with most skirts. But I have had real success with some vintage band t-shirts and skirts with opaque tights. Shoe wise I tend to go with boots instead of heels, I feel like even girlier boots still add a little bit of male-ish weight to the bottom of the look. I've not really had any success with wearing other types of heels in male mode, though I've seen some guys who have.

Also, as a sidenote, I wear kilts with shaved legs all the time and there's never been any issue with that. The kilt or a kilt-like skirt is a good starter-skirt to wear if you're just dipping your toe into the "man in skirt" pond, because it's very masculine and people tend to react to it extremely positively. It's a good way to boost the confidence that you can do more.

Without seeing a picture of you or the proposed outfits I can't really suggest more, so just the generic, but just know that even though I have been doing this pretty frequently for a while now, I still really think long and hard about every outfit combination and really ask myself, does this outfit work well together as a whole? If the answer is yes, I can wear it fearlessly, and do.

For the record, there is nothing "half assed" about how I dress. I work darn hard to look my best and I ask to please be treated with the same respect as any other member of this forum would get, thank you.