This is a tough one:
I’ve been turning this over in my brain and finally landed on what I’d say if, for example, I was besties with Marion and she popped out of her room wearing this and asked me what I thought. For reference: I look amazing in this fantasy and am both wearing a caftan and drinking champagne. By the pool. By my pool. In the south of France. While Jon Hamm grills burgers. Shirtless. No, wait, his chest hair might catch on fire — in a tight tee shirt. Okay. (Hey, if you’re going to make a hypothetical situation, make it a good one.) And what I’d say is this:
“That dress is REALLY cute! But are you going to wear those shoes with it? ….no, I don’t know, girl. I don’t love them with it. I feel like the skirt is too short for you to wear such tall shoes. The proportions are kind of weird. No! You can totally still wear a wedge. Just maybe, like, an inch or two shorter? It’d be different if the dress were a tab longer. Or if you were younger. SORRY. Sorry. Jon keeps refilling my champagne, I might be a little drunk. But, listen, girl: it’s too much leg in those shoes, and it’s not because your legs aren’t great, because THEY ARE. I just think…I mean, you know. Do you want to just stay home? We’re having burgers!”
And then she’d change them, or let out the hem, and everyone would be so so happy. Right?