Landon, Help! What Do I Wear To Coffee With My Ex?

For this week's Landon, Help!, I've got to turn the tables; I've got a question for you. My question to myself is: What the hell do I wear to coffee with my ex? A couple days ago, a text message from an unexpected (and unwanted) source sent me into a high-speed neck swirl. "Hey. How've you been? Was thinking about you the other day," it read. Against my — and basically every single one of my friends' — better judgement, I replied: "I'm well. How are you?" Fast-forward through a bunch of useless niceties and the ye olde "We should get coffee" text squeezed its way through. But, before you start yelling at me too, hear me out on why I'm even going: I guess I'm too afraid of what it'll mean if I don't. Do I know what he wants? No. Do I know what's going to happen? Not really. But, much like piecing together an outfit, it's easy to count all of the reasons why something isn't a good idea. I hope he's just as nervous as I am, because so far, this isn't fun. I've spent the past few days going over and over all of our memories — good and bad — in my head. So much so that I haven't had any energy left to figure out what I'm going to wear. I want to arrive calm and impeccably fresh-looking, yes, but I want my clothes to say I've changed. Because I have. So what does that look like, exactly? Do I go with the all-black, executive realness look? Or do I slip into my tried-and-true writer's wardrobe of jeans and a T-shirt? I've chosen these Comme des Garçons Play sneakers as my starting point because they I feel like they can go with pretty much anything. Though maybe I should wear all of his favorite items from my own closet he used to pluck right from under my nose just to stick it to the man. Kidding! (Or am I?) I hope you can help. See you in the comments below (and then again next Saturday!).