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What To Wear On Valentine's Day

What To Wear On Valentine's Day

22 Jan 2023

What To Wear On Valentine's Day

By James Shackell

It’s hard enough to find love in this crazy world, so let’s get the shoes right, yeah? Nothing spoils a Valentine’s Day outfit like dodgy shoes. It doesn’t matter how nice your jeans are, or how carefully you’ve tussled your hair to make you look like the sort of person who doesn’t care about tussled hair, wearing beaten-up sneakers on Valentine’s Day is a definite no-no. So which shoes should you wear? In this article we’re going to run through some of the better options, along with Valentine’s Day outfits for men. Thank us later.

Valentine's Day Basics

Valentine’s Day didn’t actually mean much until the 14th century, when it became known as a day of romance. The moniker comes from a Christian martyr named, you guess it, Valentine, although the true origins are a little murky. Regardless of the history, Valentine’s Day has become the hottest date night of the year, and one of three dates you need memorized (the other two being your anniversary and your partner’s birthday – forget either at your peril). Fashion-wise, Valentine’s Day is usually a good excuse to pull out all the stops. If you’re the sort of guy who usually kicks around in trainers and a hoody, popping on some dress shoes and a sharp jacket will make a seriously good impression.

Here are some outfit ideas to get your started.

Dress Shoes

A good quality black dress shoe like the CRIPPS is the obvious choice for Valentine’s Day, especially if you’re rocking a suit. (We’ve got an entire dress shoe guide, if thongs and sneakers are more your usual speed.) The basics you need to remember are: dress shoes come in all shapes, colours and finishes, so you don’t necessarily need shiny patent black leather. In fact, we’d really only recommend that if you’re going full tux. For the average guy, a simple brown lace-up like the BERESFORD is perfect. It’ll look right at home under some cuffed dark jeans and a button-up shirt. For a bit more personality, try some BENNET brogues with tan chinos and a linen shirt. Dress shoes are neat and clean by nature, so keep the rest of your outfit simple and elegant. A nice dress watch wouldn’t go amiss, either.


Loafers are a lightweight summer alternative to traditional dress shoes. And since Valentine’s Day falls in February, which can throw up the odd scorcher, this might be the way to go. A simple penny loafer like the PENLEY or FERNANDO is the best place to start. They’re comfy, discreet, and match well with pretty much anything. For a more laid-back, al fresco Valentine’s Day, try brown loafers with chino shorts and a white linen shirt. A slim ARCHIE bi-fold wallet is the only accessory you’ll need here. Alternatively, try wearing loafers with cuffed chinos and a punchy floral shirt. You can leave the crew socks at home for this look – flash some ankle with our invisible SETH socks instead.  

Chelsea Boots

For Valentine’s Day, we’d probably ditch the ever-trusty chukka boots. They’re more your weekend winery boot. Instead, try a pair of slim leather Chelseas. With their lace-less design and clean silhouette, these guys are the boot equivalent of dress shoes, and can be worn in more or less the same way. Just keep the toe in mind: for a formal dinner, or matching with a suit, you’re looking for sleek, narrow- or chisel-toed Chelsea boots. Something like the BRONSON or the OSBOURNE 2.0. Anything with a wide toe will veer towards the casual. When it comes to styling, just match these with some indigo jeans (cuffed nice and high), a collared shirt, and a lightweight suit jacket.

Suede and Nubuck

Don’t forget about suede and nubuck on Valentine’s Day, either. There’s little chance of rain in February, which makes suede an excellent choice, especially if you’re looking to avoid the starchy, suit-and-boot look. Some suede COUNTY driving shoes with cuffed jeans and a linen shirt is a casual-but-classy Valentine’s Day outfit. Alternatively you can kick things up a notch with suede Derbys, like the MORGAN, or suede Chelsea boots, like the OSBOURNE 2.0 SUEDE. Either of these would look great under chinos and a button-up shirt. Suede and nubuck are all about warmth and subtle charm, so make sure your other leather accessories aren’t too shiny or blingy. Think denim, linen and lightweight textured blazers.

Black Tie

For maximum brownie points, and because why not, you might want to consider a black tie Valentine’s Day. This will obviously only be relevant for the fanciest venues and restaurants (showing up in black tie to your local Korean BBQ joint will generate some serious raising of eyebrows), but it’s fun to go all-out sometimes. For black tie, you don’t want to mess about: black Oxfords (like the GORDON) or patent leather dress shoes (like the STONEHAM) are the way to go. These will look best with a tux, no matter the colour. For Valentine’s Day, we’d also recommend a bit of whimsy – it’s time to bust out that bow tie. Complete the look with an elegant dress watch and matching cufflinks.