The Best Outfits for Men to Wear on Valentine’s Day

Couple enjoying drinks on a date

Couple enjoying drinks on a date | iStock.com/Carlos Davila

As if you need one more Hallmark reminder, Valentine’s Day is right around the corner. Whether you’ll be spending the Cupid-struck day with your significant other or simply riding solo, make sure you show yourself some love with a handsome outfit that makes you look good and feel even better.

V Day is complicated enough as it is — planning the appropriate date night is not for the faint of heart. After all, there are just so many ways things can go wrong. Maybe you find yourself constantly feeling awkward. Or, worse yet, maybe your date is throwing serious signs he or she simply isn’t interested. Even if you had the perfect evening planned, these things can really put a damper on things.

Just know first impressions can make a big difference. And luckily, figuring out what to wear isn’t all that complex. Follow these simple and accessible ways to dress for the occasion, no matter where you might find yourself (or who you might find yourself with). From a champagne and caviar evening to a beer-and-bar crawl or an adventurous weekend getaway, these looks will get you through in five-star style.

Just a formality

You can look sharp without looking stuffy | iStock.com

You can look sharp without looking stuffy | iStock.com

If you’re planning a night that falls more on the formal side of the spectrum — say, a first-class restaurant followed by a show — then, you must suit up. But, you don’t have to relegate yourself to an uninspiring business-as-usual ensemble. If the evening will be a particularly fancy one for you, then you may want to opt for a slim-fitting, dark tuxedo or a beautiful charcoal suit. Style it with a monochromatic spin (i.e. with a black or gray button-down, respectively) for a modern twist on tradition.

But, for a slightly more informal but still plenty refined statement, spice up your tailored separates by mixing and matching; pair that precision-cut sport coat with a slick pair of black denim jeans and a checkerboard dress shirt. Remember, shoes and accessories can make all the difference here, too. A wingtip oxford with a chunky lug sole is a savvy way to add some street cred to your look. Strap on a solidly sleek watch and let a bit of that bold personality of yours shine through in an animated pair of Cupid’s bow-and-arrow socks — it’s just the pop you need to not take yourself or your outfit too seriously.

Take-out trendy

Go casual, but keep it polished | iStock.com

Go casual, but keep it polished | iStock.com

So maybe you and your VIP are staying in on Valentine’s Day. That’s okay — pop in a movie and have a picnic on the floor. But, you still have to dress to impress. No, we’re not suggesting that you wear a tux. However, here is where you can really allow your athleisure game to shine.

Give grubby sweats the boot and replace them with equally comfortable yet infinitely more stylish, off-duty pieces. This is the perfect opportunity to wear an extra-touchable cashmere sweater. And, try a pair of more tailored joggers on for size instead of those worn-out sweats. Waffle-knit Henley shirts and chunky cardigans are another handsomely adorable way to win the stay-at-home style game, where the only appropriate way to wrap up your ensemble is with a pair of equally cool, fun socks as they’ll take top billing in the absence of shoes.

Get an edge up

Handsome serious beauty male model portrait wear leather jacket

A leather jacket toughens the look | iStock.com/gmast3r

Everyone loves a bad boy. Play nice, but rough up your image a bit on Cupid’s favorite day with the tough-cool vibe of leather and denim. After all, you cannot go wrong with a touch of rebel edge especially if you’re single and ready to mingle. Throw on a black, distressed moto jacket over a V-neck T-shirt or a solid-hued sweater with a pair of slim-fitting, dark jeans and call it good. The best way to wrap up this look is with rugged lace-up combat boots. While this type of ensemble is tailor-made for a guys’ night out at the bar, it can pull double-duty for date night, too.

So outdoorsy

mixed race couple

Couple going for a hike | iStock.com/monkeybusinessimages

If hiking, camping, kayaking or anything else under the sun is in the cards for your Valentine’s Day weekend plans, then function (and stylish form) will be of premier importance. Performance sportswear and rugged layering pieces will take you from sunup to sundown. We suggest a canvas field jacket or an insulated coat that adapts to the weather conditions paired with a cable-knit sweater or a bold flannel shirt and casual chinos. Cargo detailing is okay, too — on this occasion. Or, forget those pockets, and put all your take-along gear in a sleek duffel bag. Top off your look with a knit beanie and a pair of ruddy work boots for a trendy yet practical finish. Bring on the s’mores.

Follow Rachel on Twitter @rachellw and Instagram @rachellwatkins