I went into the city with The Princess and finally met his mother. The Princess and I have been together for 11 years, and while I’ve known his kids from the start, for totally valid reasons, I’ve only begun meeting the rest of his family in the last few months. I figured the lunch ‘meeting’ could be very uncomfortable so I put my outfit together with as many of my current favourites as I thought would be appropriate. That meant my all-time favourite top – this dusty rose knit tee, my current favourite shoes (black Miu Miu’s), my cross body silver necklaces, and my new brass knuckle clutch. I figured the weapon clutch could come in handy if the lunch didn’t go well!

I tried to keep my look very ME but also very neutral. Not too edgy, not too glam. I would have loved to have worn my current favourite bottoms, which are a pair of David Kahn, Brenda Skinny leather look ankle pants, but felt they might be a bit much. It turns out I could have worn any ballsy outfit I wanted – The Princess’s mom is so seriously glam! She wore a black and white outfit: Black pants, a white button up shirt with a double collar, a micro hounds-tooth vest, and an amazing black blazer. Black nail polish (I was going to do my nails in black polish but worried it would be too goth!), and her expertly layered pixie bob completed the look. Her hair is a perfect mix of light and dark grey, blonde and white. I think she looks like what Meryl Streep is going to look like in 20 years.

The lunch went well, we got along well and were comfortable with each other. We were able to talk and laugh and share stories. Of course the things that kept us from meeting for a decade are still in play, so where we go from here is awkward and in question.

* Don’t worry, I took these photos a couple days after I actually wore the outfit, so when I met The Princess’s mom, I was crisply pressed, wonderfully coiffed, contact lensed, and dolled up in make up!