It’s getting real, friends. My 20th high school reunion is on the calendar and I’ll be attending this summer. This will be a first for me. I’m mostly excited because it means two of the nearest and dearest to my heart will make the trek from New Zealand and New York for the festivities. And honestly, I’m one of those people who generally enjoyed high school. So gathering to rehash and catch up doesn’t sound all-together horrible.

And since it seems I’ve purged all the black velvet from my teenage years I’ll clearly have nothing to wear. I’m not going to lie. I did like the idea of wearing a vintage (I do believe I just referred to my own wardrobe as vintage) prom dress but one girlfriend, who will remain unnamed, warned me that I had “better check myself” when I suggested it on a group email.

Consider myself properly checked and now, won’t you help me plan a proper outfit? Over the next few months I’ll post a series of round ups. Special pieces I think would be fun to wear for a walk down memory lane. Considering the location of my reunion, I’m pretty sure I’ll be leaning toward cocktail attire, but I think it’s fun to consider all the options.

I’m loving all three of these choices. Especially the Rachel Zoe number. Beachy waves for the hair and some rose-gold jewelry would help achieve that effortless glam look. Which would you choose?

P.S. This reminds me of a game we played in high school. Flipping through awful teen mags during prom season we’d compare two dresses – each one hideous in it’s own special way – and throw out the challenge “if you had to wear one – which would it be?” So fun. It’s also a good time with bridal magazines.