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

Photo: Courtesy of Dover Street Market.
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!).
Advertisement

More from Styling Tips

Sometimes it can feel like life is just a constant rotation between large plastic bins of clothing — as soon as you're finally getting settled into your ...
Sometimes, looking a certain height is all about perspective
You can switch out your clothes all you want, but you can’t really replicate the way glasses can completely transform you. It’s like presenting an ...
If you're like us, Beauty and the Beast was in heavy VHS rotation when you were a kid. And, if that's the case, there's a good chance you were as besotted ...
No matter what country you came from or what country you're headed to, first-generation immigrants have a tricky relationship with fashion. What's normal ...
When you're young, you get used to being asked what you want to be when you grow up. But why should that stop when you actually reach adulthood? You don't ...
This story was originally published on August 4, 2014. Even though we've all experienced most temperatures, we have selective memory about what they're ...
(Paid Content) As cooler temps signal us to switch up our wardrobe, it's tempting to go on a sweater-weather shopping bender. But considering all the fall-...
If you've ever looked at model-street-style roundups and said to yourself, Gosh, I could never afford that, or even, Yeah, but they get all that stuff for ...
Cutouts have always seemed like a really daring thing to wear, especially if you were the kind of woman who wore bras most of the time and didn't consider ...
You know this meme. You might feel closer to it than any other meme that's ever memed. It's at once an admission that things are close to ruin all around ...
There's maxi-length, which goes down all the way to the floor. There's knee-length, which hits at or below your knee, midi-length ends right below your ...
For women who subscribe to that Rachel Comey lifestyle (martinis over rosé, Brooklyn over Manhattan, jumpsuits over gowns, Bowie over The Beatles), there's...
So, there's that outfit that's been stuck in your brain ever since you came across it in a slideshow once, not only because it's really good, but also ...