Thomas Pink’s Guide To Proposing

Has your social media been flooded with viral wedding content? Or perhaps you’ve reached the natural ‘next stage’ in your relationship. Either way, we’ve all caught a case of wedding fever in 2024. But before the wedding comes the proposal. In our Instagram age, where every milestone (and meal) is #content, there can be pressure to go all out. These high expectations can make popping the question seem even more daunting than the big day itself.

Although most couples have already discussed marriage before one of them decides to formally propose, the element of surprise is still important to make that memorable moment feel extra special. There are myriad ways to pop the question to suit your personal style and that of your partner’s. Here, we offer some tips on what to do, where to go and, more importantly, what to wear...

Like your impending nuptials, a proposal should be done in a way that reflects you as a couple: your personal taste, style, likes and dislikes. So, if you know that getting down on one knee in front of a crowded restaurant would send your partner into cold sweats, then stick to what makes you both feel at ease. For more private couples, why not propose from the comfort of home? A weekday proposal will no doubt come as a complete surprise to your beloved, made even sweeter if they’ve had a tough day at the office. Or perhaps you choose breakfast in bed on a lazy Sunday with a mimosa and a ring box? But being at home is no excuse not to dress the part. If you opt for a mid-week dinner, why not set the scene with candlelight, a bottle of wine and a delicious meal (home cooked or otherwise). Dress to impress with an evening shirt such as our Bib Front Oxford Shirt made from 100% cotton, woven in Italy, complete with cufflinks and a silk bow tie. You can always slip into something more comfy after they (hopefully) say “yes.”

We may have denounced the restaurant proposal earlier, but this is a classic route for many couples. A public proposal can be done subtly, and remember that eye-watering prices and Michelin-stars don’t necessarily equate to the best proposal. It’s better to go for somewhere that means something to you both, such as where you had your first or a memorable date. Your local family-run Italian restaurant can be far more meaningful and intimate than a swanky new opening. Dress-wise, aim for smart-casual, perhaps with a classic button-down American Oxford or a Mussola Twill so you’ll keep your cool. Make sure you communicate with the restaurant beforehand to reserve your table and perhaps even involve them in the planning. Enquire about private rooms, a terrace area or a quiet booth. They could even help with arranging special décor and the obligatory celebratory bottle of fizz.

For some couples, an engagement is a full-on spectacle. Helicopter rides, weekend in Paris, cinematic backdrop with full camera crew on standby? Check, check, check. An engagement is a very special milestone, so why not make the most of it? If you are going OTT, then make sure your wardrobe is equally on point. Try one of our colourful Striped Seersucker shirts in either lilac or a pale yellow. Our signature pale pink hue is equally stylish but a little more subtle. Or go classic in a full tux with a white Double Cuff Dobby Shirt.

Proposing on holiday is one of the most popular ways to pop the question. Apparently almost three in five women want to be proposed to while abroad. It makes complete sense, especially if you’re vacationing in some of the world’s most romantic cities – Rome, Paris, Venice, Prague, Vienna. Whether you go for a city break, beach, mountains or Arctic exploration, a holiday provides the ultimate escapism, relaxation and beautiful landscapes to set the scene. Again, preparation is key. Want to bend down on one knee in front of the Trevi Fountain? Prepare to battle hordes of tourists with selfie sticks. Similarly, you don’t want to work up a sweat walking for hours in search of that ‘off the beaten track’ hidden gem (which is actually way too hidden). A quiet alfresco dining or walking spot may be the best option, or even the balcony of your hotel room. And try to avoid clichés (Eiffel Tower, looking at you) unless they have a particularly special meaning for your betrothed. Either way, you’ll want to keep you cool – both literally and figuratively. Choose a lightweight fabric, such as linen, seersucker or a cotton-linen blend with our signature styles such as our Cotton Linen Slub, or try our new Grandad Collar style for a fashionably timeless twist – elegant enough for a fancy dinner, yet with breathable fabrics to disguise any nerves.