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How to dress your way out of a breakup

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Marilyn Monroe with her lawyer Jerry Giesler following her divorce from Joe DiMaggio Marilyn Monroe with her lawyer Jerry Giesler after her divorce from Joe DiMaggio. Photograph: George Silk/The LIFE Picture Collection/Getty

Coco Chanel once said: “If you are sad, if you are heartbroken, make yourself up, dress up, add more lipstick and attack.” She certainly knew a thing or two about heartache. For 10 years, she was the mistress of polo player and renowned playboy Boy Capel, a man she described as the love of her life even though he married someone else while he was with her.

Sartorially speaking, heartbreak can be the making of someone. I was recently broken up with over text message (iMessage, to be precise) and plotted a thousand fashion revenges, many to be curated on Instagram – documenting a multitude of minuscule, date-hinting outfits.

Coco Chanel 1936 Coco Chanel in 1936. Photograph: Lipnitzki/Roger Viollet/Getty Images

“For Chanel and young divorcee Madeleine Vionnet, their single status (atypical for the time) meant radically rethinking their relationship to the male gaze and therefore to style,” explains Alice Litscher, a professor in fashion communication atthe Institut Français de la Mode in Paris. “Vionnet’s loose bias cuts or Coco’s tweeds expressed a radical sense of liberation from classical femininity and seduction.”

In the case of Isabella Blow, her humorous hats were a distraction from her painful separation from Tim Willis; for Marilyn Monroe, who first appeared in sleek black clothing after her divorce from Joe DiMaggio, it allowed her to move away from her cheerful pin-up image.

Instead of following my probably regrettable reaction, here is some expert advice from women in fashion who understand the pain of a breakup about how to navigate three of the trickiest post-breakup scenarios:

The getting your things back

It’s safe to say you probably weren’t in the best state the last time you saw your ex. If the last memory you left of yourself included crying, door slamming or screaming your head off in a public place, restoring a sense of calm and ease is advisable. Wear something that doesn’t look too over-thought. I’d go for Gap skinny jeans (in a size that fits, rather than one you’d like to fit into), and a black T-shirt or Bompard polo neck.

Lauren Sherman, a New York-based fashion writer and contributing editor to Business of Fashion, says it’s all about pairing comfort with low-key yet flattering pieces. “When you’re seeing your ex for the first time since you broke up, it’s nice to wear something guaranteed to make him think: ‘Wow, she looks great.’ The key is to wear something effortless, such as a slinky T-shirt and skinny jeans. The most important thing is that you feel good in whatever you’re wearing. The more comfortable you are, the more comfortable you’ll look, and they’ll sense that.”

Word to the wise: avoid heavy makeup in case you feel emotional at the sight of your belongings neatly packed in bags (I’ve been there, and it never gets easier).

Isabella Blow at Frieze Isabella Blow at the Frieze art fair in London. Photograph: Dave M. Benett/Getty Images

The first night out on the town

The first night out is a key moment, but while you might be tempted to dress sexy to attract attention and regain the confidence you lost, this isn’t always the best solution. You’re pretty vulnerable and ogling strangers won’t help. Instead, try something you never allowed yourself to wear while you were in a relationship (let’s face it, your style is always – consciously or not – adapted to what you think the other likes or dislikes).

For Chanel model Anna Cleveland, a recent breakup meant cutting her long locks into a neat, straight bob. “It was time for a ritual, so I chopped off my hair. It symbolised the weight of the past being lifted off my shoulders, liberation and spiritual newness.” Fashion should be a crutch and a way to have fun, she says.

For me, that meant wearing bold colours and conceptual prints – something like this from & Other Stories in the colours of the aurora borealis because, why not?

The mutual friend’s birthday

This is one of the worst scenarios because he or she knows you’ll be there and there is a chance you’ll meet their new partner. It’s important to rise above it and look appealing without trying to make them jealous by flirting with an entire room.

“Wear something that guarantees elegance, comfort and a sliver of sex appeal,” says fashion stylist Natalie Yuksel. “This is not the time for experimentation; the situation is awkward enough as it is. Discomfort or trying too hard will immediately show. A perfect little black dress and heels you can walk in are ideal.” I like Alaïa-esque thin knit dresses that make everyone look fabulous (almost) by accident. Zara make its own great version.

Aside: if you’re going alone to the event and are not planning to kiss anyone, this is the perfect time to wear bold lipstick and actually have it stay on your lips for once.

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