Ah, Valentine’s Day. I remember our 2nd Grade class getting loads of pink cardboard paper and glitter to create cards for “our valentine,” not knowing what that was. Then I found out. A good way to jump-start anxiety at an early age. Fortunately, I was exempt, because if you’re like me (you know who you are), every day is Valentine’s Day!

But let’s say you want to take your SO on a special date. What do you wear? The answer to that depends on the situation. Dinner and a movie? Opera and cocktails? A walk on a moonlit beach? Decisions, decisions.

The quick answer is: be you, but a bit nicer looking. You could show up in your pajamas, but dressing up demonstrates respect for your date and the occasion, because both are special, right? Right. Unless the date is a pajama party. In which case, wash your pj’s first.

VALENTINE’S DAY DATE FOR NEW COUPLES

For new couples, keep it casual. If you’re meeting at a coffee shop, wear a nice pair of jeans or khakis, a button up oxford, and clean sneakers or oxfords. After coffee, why not take a walk at a nearby park? Or better yet, find out what activities she likes – hiking, bicycling, karaoke – and plan around that.

Shawl collar jacket: Eidos | Long-sleeved t-shirt: Orcival

Of course, just because you’re a new couple doesn’t mean you can’t get all fancy. If you’re date’s down for a night on the town, go for it – and dress accordingly. If you start with dinner at a nice restaurant, go for a dark outfit. It’s safe, unfussy, and easy to dress up or down, depending on where you go. A fail-safe option is a navy suit. Pair it with a crisp white button up shirt, or swap the shirt for a thin charcoal or black merino turtleneck. If dark jeans are your thing, reach for black Chelseas or zip boots, a blue oxford button down, and a grey tweed sport coat or field jacket.

Shirt: G. Inglese x Beige | Pants: Husbands

A SPECIAL VALENTINE’S DAY DATE

Perhaps you’ve been together for a while now, and are looking for something special to do. Show that you were paying attention – you were, weren’t you? – by choosing something she said she liked to do. It could be a picnic, wine tasting, or a leisurely walk to a park, downtown, or movie theater. If you have access to a beach, lake, or river, walk there, and bring a frisbee with you to enjoy the sun – everybody can play frisbee. All you need are a nice pair of jeans, boots, and a nice button-up shirt.

However, when it’s a special occasion that calls for something a bit more formal, consider what she’ll be wearing. Being over- or underdressed can be a bit embarrassing, so set the tone by saying “Let’s dress up,” and be sure to follow by saying what you’re wearing so that she can have something on which to base her decision. On the other hand, she could have that one outfit that she’s been dying to wear, so let her choose and follow suit. What if she says she has nothing to wear? Besides starting an argument (don’t do it), you have two options: go shopping with her (that’ll score you major points) or tell her far enough in advance so she can plan to go shopping with friends. Whatever she chooses, be a gentleman and let her take center stage. You may have the perfect red velvet cocktail jacket, but be careful not to outshine your date; remember that this is her night. Show that she’s important by taking her into consideration. For example, ask her what her favorite outfit of yours is and wear it. Or find out what her favorite color is, or which one she’ll be wearing, and chose a flower or pocket square that complements it.

Shirt: The Armoury | Pocket Square: Drake’s

SOMETHING DIFFERENT THAN A DINNER…

Dinner and a show is always a safe bet, but why not try something different? Go to that one restaurant she’s been dying to try, and then follow up with a dancing class. Or you could go to a club that plays her favorite music. Many museums have evening hours, perfect for an after-dinner stroll and providing easy topics for conversation. If black tie is too formal, a nice suit, comfortable shoes, and a listening ear are all you need to enjoy your time together.

Pro tip: if she likes perfumes, start the evening out by going to a department store and trying scents. Let her pick one for herself, ask her to pick one for you, drop your bank card, and the rest of the evening is set. You’re welcome.

Evening date – houndstooth flannel suit and rollneck.

Grey flannel suit: Eidos

Navy turtleneck sweater: Stephen Schneider

Any date, no matter the day, is an opportunity to show your partner that you care about your relationship. Let your dress reflect that by notching it up a bit. These are occasions to engage in relaxed conversation, have fun, and cement your relationship. The special dates are your chances to create long-lasting memories. Don’t let your dirty sneakers ruin it.