Valentines Day Outfits for Any Destination

When Valentine’s Day falls on a weekend, you know you’re in for a (re)treat. And it doesn’t matter whether you’re in a long-term relationship or playing the singles game with some friends, a conveniently timed holiday is the perfect excuse to get away for some R&R. If you’ve stared down the coming calendar like we have, you’ll have already noticed that this year is a bit of a double whammy. A Sunday lover’s day coupled with an extra Monday (thanks to Presidents’ Day!), sets this romantic weekend up to be one for the record books. And, you know what that means. You need some inspiration for Valentines Day outfits that will fit the bill.

Island and European getaways are among the most popular picks on travel sites, but if you’re late to the planning game, a quick trip to your nearby mountain range or a city staycation are some of our favorite options, too. Whether you’re in on the itinerary or in for an exciting surprise, if you know the climate you’re headed to, celebrate in style with our simple guide. These pretty little pieces dress you up for your desired destination with just the right nods to devotion and decadence.

Valentines Day Outfits by Destination

In the City

Whether you’re staying in town or visiting you two’s favorite city for a weekender, you can still play to the occasion with an evening out look that winks to Cupid’s holiday. Raise a glass to these picks we love: rosy outfits and accessories that you can continue to work with in later months.


Lace-Up Paisley Romper, $34.90, Forever21


Charles Gray London Kimono Coat, $89.91, Nordstrom Rack

Tropical Escape

If you and your lovebird are migrating to warmer climes for V-Day weekend, you’ll need to pack up the summer clothes. Island destinations call for an easygoing spirit–and closet–so while you’re sipping mai-tais or grabbing a couples massage, light and airy are just the ticket.

Sophia Border Print Tie Front Maxi Beach Cover Up, $30, Boohoo

Steve Madden Dayyn Sandal, $69.96

Mountain Getaway

From your own cozy cabin to the bustling lodge and powdery slopes,  you’ll want your winter wardrobe to be in overdrive. But if you’re wondering how all those extra layers will affect your weekend, remember that romance doesn’t automatically translate to skimpy. You know what’s sexy? Snuggling. Even sexier? Snuggling in plush fur with a hot toddy buzz.

Hotel Spa Women’s Velvet Spa Robe, $29.99, Target


Wooden Ships Heart Pom Pom Black Snow Beanie, $21.97, Nordstrom Rack


Melissa is creative communication professional with 9+ years of experience writing for the beauty and fashion industries.