Upcoming Dinner Date - Can you help me with what to wear?

Hi everyone. I have a date!!! I've been crossdressing (MtF) for a little while, but I've never had a chance to get all dressed up to impress SOMEONE ELSE! I'm so excited.

I'm 5'7", 148 lbs. with an pretty athletic, trim body. I love getting out dressed up, in general, but I've never done anything more the basic casual (skirt, top, flats or boots) for going to dinner or to the mall, usually by myself.

Anyway, I recently had a guy (who knows I'm a cd) ask me out. He wants to take me to dinner at this swanky restaurant and then out for a glass of wine afterwards. I've known him for sometime and trust him completely. However, having never been on a date on this side of the table, I'm super excited. I really look forward to being treated like a lady. That said, I've also never really thought about what I'd wear on a date such as this. I'm willing to shop/spend some money on this, since it really is something I'm looking forward to.

Any input would be really appreciated (links to cool stuff would be even better). If there's any other info I can provide, just let me know.

Thank you SO much!


What Guys Said 1

  • wear something simple not over the top or trashy


What Girls Said 1

  • I suggest going with a blazer, dress pants, and pointy heels for a more feminine touch.
    You are a guy cross dresser, I don't think a dress or a skirt would look good on a guy's body. I think it would look too awkward. In my opinion it's better if you went for an androgynous look. To make it seem like you're cross dressing, obviously you're going to shop at the women's section. The fitting of women's blazer is different from the one for men, it accentuates the figure more. If this look option isn't feminine enough for you, then you could always go for really flared pants or culottes.
    Here is an example of what to wear if maybe you want something glamorous
    Ignore the top, just the sequin bottoms
    Notice how the glam bling bling outfits are more girly, I'm assuming you would like them better, lol. Anyway, if you are cross dressing, stick with pants and something long sleeved.