Ha! Well, she has good taste just like you! 

Perhaps also, though, seeing her looking good in the dress triggers some emotions in you such as envy or sadness? I can see where it might. It’s hard to be a trans woman. We want to appear just as nice as another woman and sometimes that’s just a bit of a bridge too far. And, like all women we compare and often negatively judge ourselves versus other women. So unlike being a man, right? 

So, you rock that dress! Have a fun time wearing it! And tell her how nice she looks in it. Women often complement each other.

Good advice, as always. I recently read that envy is not necessarily a bad thing in that it points where we strive to be. I know I can't look like a woman, such as I am. I guess I can just try to be the best looking me while dressed--even if it's only for me. BTW, I'll let you know if I make my goal--a little distant, but who knows?

Dear MichelleLea and Emma,

Think looking APPROPRIATE and REALISTIC should be your goals looking like you are women, because you ARE women.

Most older women emphasize CLOTHING and ACCESSORIES.

Went out with my friend yesterday, and no one bothered us. She was a transwoman, aged 71, and I am a cisgender woman, aged 60.

Try to get out with friends, as I find it so healing.

Your friend,

Monica

I agree Monica! This evening I was taken out to dinner by a couple of friends to a hip restaurant along Lake Washington. I wore sandals, skinny jeans, a pretty and flowery top, and a white sweater. We had a blast! 

It can be challenging to determine ones style and then making it a reality. I think it’s good advice to notice what others wear that you like and then to try to follow their lead. It’s  expensive though and I was tempted to buy lesser quality clothing on Amazon among others. I’ve had a lot of success at women’s clothing consignment shops which try hard to carry quality items (which don’t sit around). Go often, experiment, and try not to buy anything - no matter how “cheap” - that you don’t absolutely love!

Dear Emma,

Very well said. Great advice no matter who you are!

As for myself, I try to go for a TAILORED look. 

Two dear friends from Philadelphia, PA, send me wonderful T/LGB magazines that I learn a lot from. When I plan on visiting them, I hope I will have saved up some money to buy at some of the stores/boutiques featured in the magazines.

Your friend,

Monica

I have to agree that cheap clothes just don't ever look or fit right. I will have to experiment with going out looks--first, I have to find someone to go out with. Maybe it's time.

I think it’s hard to figure this stuff out and unless whoever goes with you is a fashion expert whose style you love, well, I think you’re better off going on your own. And then only buy things you really love. Check out the return policy so you give yourself a few days to reflect and consider. 

Dear MichelleLea and Emma,

Love shopping for clothes with a girlfriend as I feel two heads are better than one!

Even if my sense of style is different than hers, I would like her input, after I shared with her what I am trying to achieve and why, and vice versa.

Your friend,

Monica