Navigating the high seas of Valentine’s Day gift-giving can be akin to performing a delicate dance on a tightrope made of rose petals. On February 14th, the pressure mounts to find that perfect symbol of affection, one that says, “I adore you,” without accidentally whispering, “I forgot until last night.” The art of choosing a Valentine’s gift is less about the grandeur of the gesture and more about mastering the subtle nuances of your partner’s likes, dislikes, and those unspoken wishes they think you haven’t noticed.

Forget the old standbys of chocolates and flowers, unless your significant other has explicitly stated their undying love for confectionery or botany. In the realm of love, creativity and a dash of humour can elevate your gift from obligatory to legendary. Imagine gifting a plant that, unlike your traditional bouquet, refuses to wilt under the pressure of your relationship’s expectations. Or consider a mixtape (yes, a digital playlist for the modern era) filled with songs that recount the epic saga of your love life, including that time you both got lost but found a great diner by accident.

Choosing the right gift is about striking a balance between heartfelt sincerity and acknowledging that love, in all its forms, includes a healthy dose of laughter and light-heartedness. It’s about saying, “I get you,” with a gift that perfectly encapsulates your inside jokes, shared experiences, and mutual dreams.

Check out our favourite Valentine’s Day Gift Guide curated by the ICON team below.

Valentine's Day, Coach
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COACH LEAGUE MESSENGER BAG, $725, SHOP NOW

A bag to take you from A to B in a New York minute.

Valentine's Day, Chanel
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CHANEL CHANCE EAU FRAÎCHE EDP, $285, SHOP NOW

Flowers fade but a Chanel fragrance is forever. Gift your significant other with a new signature scent.

Valentine's Day, Valentino
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VALENTINO VLOGO TOILE SANDAL, $1480, SHOP NOW

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PERRIER-JOUËT BELLE ÉPOQUE CHAMPAGNE, $350, SHOP NOW

Taste can definitely be bought and it comes in the form of a vintage cuvée. Exquisite and subtle.

 

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RALPH LAUREN SITTING POLO BEAR WATCH, $2980, SHOP NOW

Who doesn’t love a bear hug on Valentine’s Day?

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BOTTEGA VENETA BATHROBE, $890, SHOP NOW

As cozy as a cuddle, only better because it’s Bottega Veneta.

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PRADA SATIN MULES, $1690, SHOP NOW

In some myths, green is associated with the planet Venus, the planet of named after the goddess of love and trust us when we say that you’re loved one will love these Prada shoes on Valentine’s Day.

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GUCCI BOWLING BAG, $3610, SHOP NOW

It’s not just a bag, it’s a piece of history and a nod to Guccio Gucci’s time as a hotel porter. A spectacular accessory that speaks volumes.

 

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LOUIS VUITTON SILK SHIRT, $3700, 

This pyjama shirt can either be worn with the matching pants as actual pyamas or swapped in as an evening shirt for that rakish style.

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NEW BALANCE 1906R SNEAKERS, $230, SHOP NOW

There’s no substitute for footwear that fits like a glove and looks cool while doing it. A gift that comes from the heart.