Cross-dressing the Part

An actual letter from an actual reader:

Hi,

I have been wearing high heels, short skirts, dresses, blouses, chiffon tops, etc., which are all fine but since I am a guy, I guess that is just weird!

I am planning in telling my girlfriend but I want to look my best. What do you recommend, and no, I'm not wearing my male clothes to do it.

I want her to see me as the cross dresser that I am. She will probably finish with me but I still want to look my best, as I love the clothes more than her so its only fair to her to be totally honest with her.

By the way, I'm not gay, not even the slightest bit. I like female company but love the clothes.

What do you recommend?
J.

Well J., this is quite the dilemma for you, isn't it? On one hand, you want your girlfriend to see how fabulous you look in a skirt and heels. But on the other hand, if you look hotter in a dress than she does, that literally adds insult to her injury, doesn't it?

But I suppose if you're going to do it, you gotta do it right. And looking fabulous is my specialty, so you've come to the right place.

J. specified that his favorite pieces are pencil skirts and chiffon blouses. Pencil skirts are almost universally flattering. My favorite way to wear them is with a peplum jacket.


This suit from Pink Tartan may be a bit more buttoned-up than J. is looking for. Here's another option, from Victoria's Secret:


Although it obviously needs a blouse. I recommend something in a vibrant color, with ruffles. Finish off the look with a pair of sexy sling-backs.

All this can definitely be a flattering look, but I'm not sure I would call it fabulous. It's a little business-like, no? I think you really need to kick it up for this auspicious occasion. I'm thinking DRESS. Like this cowl-necked dress from Banana:

which is really feminine and flattering but needs a belt around that elasticized waist. Or this watercolor wrap dress:

which is soft and flowy and lengthening and come to think of it, would be really cute on me. Wear with the dresses a pair of kick-ass pumps.

Now J., we need to talk about your legs. I understand that men who enjoy wearing women's clothes tend to especially enjoy outdated and uncomfortable underthings. Now, I don't want to deprive you the joy of garters and stockings and such but we need to lay down some ground rules here.

First, bare legs are preferable to nude hose. No one wears nude hose. I personally never wear any hose. Tights in the winter - okay, but I really despise hose. Second, stockings over hairy legs is a most unattractive look. I can't sign off on that at all. If you are opposed to shaving your legs then I have to recommend you go bare or stick with opaque tights.

Lastly, I don't know where you stand on jewelry, J., but let's not forget that the only thing that separates us from the animals is our ability to accessorize. So pick out some long necklaces, or a cuff bracelet or some chandelier earrings to make sure your look is finished off.

So you're all set then. Best of luck to you. I hope your girlfriend is understanding about your interest in pretty clothes. Please let us know how it goes.