Dress Code: What To Wear When You're Meeting The Ex

Since we started this series, the questions have been coming: you’re meeting exes, and exes’ new partners, and your current partner’s exes…and you may want a social/aesthetic challenge. So, what to wear?

In a perfect world, we’d all be so secure and mature and self-confident that these inevitable encounters of modern existence would trouble us not at all. Or, alternatively, when we broke with people they’d magically disappear into some kind of parallel universe and never be heard from again. For some of you, perhaps one – or both – of these is the case. But for others, coming into contact with an ex – yours, mine and ours – is pretty much one of the most stressful obligations of adult life. And the truth is that what you wear is one of the few factors that, in most situations, you can control – so let’s try to get to a point where we don’t need to think about it.

Where normally I think it’s fun to give a few specific outfits, this is one case where I don’t think it’s helpful. This isn’t about “how sexy to go” or some kind of Rom-Com revenge fantasy. Rather, as in any stressful situation, you just want to not have to think about your appearance and, when you do, realize you look like the best version of yourself. With this in mind:

If you have a magic garment, wear it. No, I’m not talking about Spanx or wonderbras here. Rather, if there’s something that, for whatever reason, makes you feel confident, attractive, lucky, now is the time to break it out.
Be comfortable. Always, but here it’s non-negotiable. A stressful – or even just loaded – encounter is no time for painful heels, flesh-digging boning, cruelly tight jeans or a top you’ll be uncomfortably tugging at all night. What’s that they say about slow-cookers? Set it and forget it? That’s basically what I’m talking about.
Look like yourself. Unless, for some reason, you find it more empowering to be in costume (which I respect), this generally isn’t when you want to go for a Sephora makeover. Although that’s an ice-breaker, which is good. I find whenever I’ve tried to do something dramatic for these events – a haircut, or a facial, or a new getup – something has gone horribly, hilariously wrong and I’ve ended up having to wear my old stuff/a ponytail anyway, been out money I couldn’t afford, and been schooled by the Universe to boot.
Que Sera: The truth of the matter is, if someone, from a point of insecurity, wants to find fault with you, they’re going to. And this has nothing to do with you or what you’re wearing.
That’s what friends are for. Seriously. A supportive friend who will reassure you about what you’re wearing is invaluable. Just make sure not to ask the “brutally honest” one. Or your mom.
Oh, and don’t bother looking for sympathy. The person whose ex you are meeting, or whom you’re currently seeing when you meet the ex, will not, I repeat not, understand the importance of the sartorial decision. Partially because you’ll be so busy whistling a happy tune and being super-confident that it won’t occur to them that this is one small thing you’d like to feel good about, and could maybe use an extra compliment. No, all this will be lost on them, and this is yet another reason to consult with the above-mentioned supportive friend.
Break out the confidence song. Need it be said? Play the music to which the most awesome, gracious, confident version of yourself tosses her beret in the air in the movie of your life. Or something.

Now, to get more specific! One reader wrote to say that she was meeting an ex for the first time since their breakup and wanted sartorial advice. To which I say – beyond being yourself, dressing in you-drag, and being comfy – this is a person who knows what you look like and how you dress. While the whiz-bang makeover moment is vicariously satisfying in movies, I’m not at all sure of how confident this looks in real life. That said, I’d also advise against wearing something that has special significance for the two of you – that’s just messy. It’s human nature to want to look good, but dressing for battle gets things off on a weird note.

To the woman nervous about meeting her fiance’s ex, just remember: it is not a competition. Yes, that might be hard to keep in mind, and yes it’s hard not to revert to one’s worst insecurities, but if ever there was a time to be the best version of yourself, it’s now – and I’m not just talking sartorially. There are too many X factors here to say much beyond “don’t try too hard” – but here is a good rule of thumb: if they have no relationship, it doesn’t matter anyway. If they do, chances are you two will actually have something in common. (Yeah, I’m a Pollyanna. But whatever, she walked.)

One good thing: many of these meetings take place at weddings which is nice, because you’ll kind of be looking your best and, really, there’s nothing wrong with that. Indeed, a friend recently asked my advice on whether or not to splash out on a new dress she kind of didn’t need for just such an occasion. I said if it would help her confidence, to go for it. And afterwards, said she’d needed every extra, silky, understated-but-chic, I’m-down-to-Earth-but-effortlessly-stylish ounce she could get. And let’s just say: the wearable kind of Dutch courage looks a lot better in photographs.

When it comes to being that old partner, well, I’m a big believer in being the bigger woman. (This assumes a relatively clean breakup, if you’re meeting the new guy or gal; when things are really ugly, we all know to call ahead and, if we know there’s a potential meeting, avoid it.) So! Yes! Assuming this is a reasonably clean break with at least the semblance of politeness, and you’re all adults, and no one left anyone for anyone else there, I do think it’s nice to take the lead and make things comfortable. Clothes-wise, this means unintimidating and friendly. (And if you happen to be INCREDIBLY STYLISH and only own effortlessly gorgeous pieces that look amazing on you, well, them’s the breaks, really.) I wear a button-down denim dress, but then I always wear my button-down denim dress, because it’s kind of odd enough that it’s always slightly unexpected, and always vaguely inappropriate, which I choose to believe is just another way of being always vaguely appropriate. Like I said, magic garments.

And I look forward to hearing more from those of you who’ve got sartorial tips on weathering the meet-up!