Get your own personal stylist to help you find clothes you love. All online, completely free

Sign In

Style Advice

Style SOS: What do I wear on Valentine's Day this year?

Style SOS: What do I wear on Valentine's Day this year?

"My partner and I still want to do something low-key and special for Valentine's Day this year, even from home. How do I show her I care about how I look without dressing up in a suit and tie?" - Mikey via Instagram

As with every holiday in the past 12 months, Valentine’s Day 2021 is set to be a little different than usual – but that doesn’t mean it has to be any less romantic. In fact, what better way to express your love for another person than sitting at home with them for an entire year and still wanting to celebrate the 14th February together? 

We don’t blame you for wanting to strip the sweatpants and take on something a little smarter to make the day feel extra special. Simply ditching the sofa and having your work-from-home desk double up as a dining table for the night could be all it takes to feel like you’ve made an effort in the midst of an unromantic pandemic.

For those who don’t live with their significant other, perhaps a Zoom date or a romantic walk is on the cards? Whatever your plans, we get that a suit and tie – and possibly even shoes – aren’t going to be necessary. But that doesn’t mean you can’t scrub up for the occasion to show your partner how much you care about them (and yourself).

The date: dinner at home

If you’re staying in and cooking (or having Uber Eats serve as your home-restaurant waiter), then chances are you’ll still want to prioritise comfort. Skinny jeans and a tight shirt weren’t the best look for date nights a year ago – now it’s time to ditch them officially. But instead of your scruffy sweater, opt for a smarter rollneck or even a relaxed-fitting shirt or polo. We can’t predict your thermostat, but if your house tends to run warm then a crisp, clean t-shirt could even do the trick. At this point, as long as it’s not the spaghetti-stained hoodie you’ve had on for the past week, your other half will probably notice the effort.

Once you’ve selected either a well-fitting sweater or knit, or spruced-up shirt or tee (or a combination of the above), it’s time to match up the bottom half. If it’s been a while since you wore jeans, ease into smarter dressing with a pair of cords or relaxed-fitting chinos. They toe the line of smart casual without feeling as restrictive as denim, so you can stick within your physical and sartorial comfort zones without looking scruffy. As a rule of thumb: if you’d wear it to a casual lunch with friends, you can wear it for Valentine’s Day at home.

The date: the Zoom hangout

You might think that Zoom dating means you only need to think about your top half – and you’re not entirely wrong. It’s definitely not the right setting to subtly show off your sneaker collection. But unless you plan to sit at the screen without leaving for food, drink, or other breaks, your date is likely to be lucky enough to witness what you’ve got going on on the bottom half, too. We’re not saying your focus shouldn’t be on your top – just that, if you think you’ve wormed your way out of wearing a full outfit, you thought wrong. 

Since you (probably) don’t live with your date right now, this is a winning opportunity to bag some points for effort by making a good impression with your shirt. While the stay-home guys could pass in a clean tee, for your Zoom date we advocate for full collars. If an Oxford shirt feels too much, try a long-sleeved polo that combines the smart feel of a shirt with the casual comfort of a tee. Trust us: when it comes to collars, they’re the easiest way to show you’ve made an effort, effortlessly.

On the bottom, go for a comfy pair of drawstring trousers. Cotton slacks or chinos with an adjustable waistline have the appearance of formal trousers, but the comfort of sweatpants. So since you’re likely to spend most of your Valentine’s evening sat down, they’ll be the best option for looking and feeling like you’ve made an effort without distracting you with discomfort (and no, sitting there with your jeans undone is not a viable alternative).

The date: a romantic walk 

If you’re heading outside for your Valentine’s date, you’re erring closer to the ‘normal’ dating dress code than anyone else. Whether you’re long-time partners or new beaus, an outdoor date is the best setting to impress with your outfit. Let outerwear lead your look and opt for a classic style like an overcoat or a trench. They’re the perfect starting point for your outdoor outfit since they’re timeless and go with just about anything, so no matter what direction you take underneath, you’ve at least presented a considered exterior. 

Since it’s February, you might want to opt for a chunky knit or rollneck. But if a shirt or tee is more your thing, make sure they’re fresh and ironed. We know you probably forgot you even own an iron, but if a Valentine’s Day date isn’t the best reason to dust it off, we don’t know what is. On the bottom, chinos, cords, or a pair of selvedge denim jeans will work to combine casual dressing with an air of sophistication. You’ll feel comfortable but look effortlessly stylish – especially if you finish the look with a pair of lace-up leather boots. If you prefer trainers, just make sure they’re as close to box-fresh as possible. 

You should also bear in mind that you’re likely to feel the cold on your walk. But don’t ruin the date by complaining about the predictable winter chill. Instead, come prepared with a scarf and/or beanie – and, of course, a bunch of roses.

Words: Ella White
Illustration: Guy Fields