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1-234-755-CHAT: What Should I Wear To Break Up With Someone?

In this edition of 1-234-755-CHAT, a caller wants to know if there are any fashion dos and don’ts when breaking up with someone.

“Hi. I’m going to break up with my boyfriend tomorrow afternoon. We’re going to get a coffee. What do I wear? Just be normal or do I need to look super ugly or something?”

First, bummer for the break up but probably for the best. (And hopefully the poor dude won’t be shocked and, if he is, that will affect what you should wear.) You can take this in a few directions, pending the circumstance. I would say as a rule to not “look your best” but to “look your best.” This is because you will want a clean break. If you are doubting yourself and or want break up sex, look your best. You know what I mean.

Go simple. You’re just getting coffee so what you would normally wear out should work. Don’t wear aggravating footwear in case you guys extend the breakup period to an annoying walk-and-talk about feelings. Do bring a sweater or jacket for that reason, too. If it gets cold, you don’t want to borrow anything from him.

I would stay away from something memorable. If we’ve learned anything from country music, it is that the way you look (and any memorable clothing) will be used in a song lyric for a breakup anthem. Go for jewel tones and nothing too tight. Don’t wear all black because he’ll start crying: you will have dressed for your relationship’s funeral and that will make you both depressed.

If this is a surprise, to him, and you are excited to salt him in the wound, go all out sex. Wear something that says, “Yeah, fuck you mother fucker: you fucking missed out on this fuck. Fuck you.” This will make it all the harsher and could possibly speed up your rebound opportunities.

For further information, you should watch this.

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