10 Comfortable (and Cute!) Valentine’s Day Outfit Ideas to Copy (2024)

Love it or hate it, Valentine’s Day is coming—and if you haven’t already seen chocolate hearts and cheesy cards in every shop, buckle up. We all know in our heart of hearts that Valentine’s Day is a Hallmark holiday but listen: It’s the middle of February, winter is still raging it’s ugly head, Christmas is a distant hangover, and frankly, we need something to celebrate.

Even if you historically loathe the day of love, why not embrace it this year, no matter where you currently are in your love life. Whether you’re very single and ready to mingle or preparing to celebrate what seems like your 97th Valentine’s Day with the same partner, spice it up with what you wear! Below are a few Valentine’s Day outfit ideas suggestions depending on your current relationship status or date plans.

The First Valentine’s

The first Valentine’s day is always special: a bit of nerves, a bit of excitement or a bit of total shock if one member of the couple is completely unaware that they made plans on “the holiday.” I personally think it’s crucial not to go over the top here. Let’s hold on the red-heart tights and “I Love You” sweater and save that for the second Valentine’s Day (if you make it that far). I’d take a subtle yet festive approach and wear excellent-fitting jeans, a top with a pop of red or pink, and some fun accessories and dainty lingerie (for your own confidence boost, natch). This formula works for dinner in a chic restaurant, an at-home meal, or something off-piste like…bowling. (Note to self, if you are going bowling, choose your socks wisely, preferably ones without hearts on them…)

The Getaway

If you’re getting away from your daily life/habits/routine for Valentine’s Day then it’s also the time to dress away from your daily life. If you’re normally a jeans and top kinda gal but headed to the beach, try a charming dress or playsuit. If you’re planning a weekend trip to a nearby town or staycation in your own city where you tend to wear dresses to work, then go for a casual but polished combo with a knit and cool, corduroy trousers. The memo here is that whatever is normally “off limits” in your day to day—now is the time to embrace the opposite. Besides, traveling allows us to try on various versions of ourselves and what better way to do that than with your outfit?

The Partner of Many Years

You know the saying—“You can’t teach an old dog new tricks but you can get an old dog new lingerie”? Ok, maybe that’s not the exact wording but it’s something along those lines, which I do think applies here. If your beloved partner has zero expectation for you to open the bedroom door in something beribboned and crotchless, a delicate cami set with a sweet lace trim is just the ticket. If it’s just you dining à deux on the couch and watching Netflix in your pajamas, upgrade that set to a silky pair to spice things up ever so slightly.

The Single and Ready to Mingle

Whether you’re single and ready to mingle or single-and-happy-alone-thank-you-very-much, Valentine’s Day can be a day to celebrate yourself. If you’re on the hunt for a partner, the best way to attract someone is with confidence so wear whatever makes you the most comfortable and your confidence will radiate—be it your favorite LBD, a perfectly worn-in leather jacket, thigh-high boots…whatever it is, you do you.

The Galentine’s Day

If Valentine’s Day is all about celebrating love then let’s not forget some of the most important loving relationships in our lives: our friends. “Galentine’s” is really just another word for what is, in fact, a girl’s night out—as if we needed any excuse to get dressed to the nines with our friends (be it in pajamas to wear to bed or pajamas to wear out). For these Valentine’s Day outfit ideas, think something with feathers, something with satin, or big bows that you might normally stay away from—this is your night to shine!