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6 Valentine’s Day Date Ideas + What to Wear

February 13, 2023

6 Valentine’s Day Date Ideas + What to Wear

Whether you’ve celebrated Valentine’s Day with your wife for years or it’s your first V-Day with a new partner, chances are you want to look good on the big day. Still, it’s worth acknowledging that people have all kinds of feelings when it comes to Valentine’s Day. Some folks love it, others could care less. Some people might feel extremely nervous, while others feel at ease with their date. No matter how you feel, looking good can provide a little confidence boost that can improve the mood of the entire holiday.

With that said, coming up with the perfect date and the perfect outfit is no easy feat. That’s why we’ve put together six simple yet well-rounded date ideas for you to choose from, no matter what your relationship status is. We’ve included the perfect outfit for each so you’re ready to go.

1. The Dinner Date


 Valentines Day Dinner Date  mens dress shoes

The dinner date is a Valentine’s Day classic - and for good reason. You get to enjoy a delicious meal and it’s typically just quiet enough to be able to carry a conversation. Plus, you’re getting a shared experience, giving you an easy topic of conversation - that could be a big benefit if you’re nervous. Just be sure to book a reservation well in advance, as finding an open table the night of Valentine’s Day is nearly impossible.

A dinner date is also an excellent excuse to dress up and show off your nicest pieces. We recommend wearing a well-tailored, slim-fitting suit. Opt for a tie or leave it off for a slightly more casual feel. Throw on a nice pair of oxford dress shoes, making sure to match them to your belt.

2.  Chef’s Night-In Date


 Casual Date Jeans

 Date Sweater

If you’re looking for a more intimate Valentine’s Day date, consider staying in. You can either prepare a meal for your guest of honor or find a fun recipe and cook together. Spending time in the kitchen, playing music, drinking wine, and chatting can build a sense of connection and rapport with your significant other. Plus, if you aren't a great cook, it can even result in some laughs. Be sure to pick out a few recipes and send them to your date ahead of time, letting them choose what you’ll cook.

A date night in requires a bit of balance in your outfit. You don’t want to be overdressed, but you also don’t want to look like a slob. We recommend a pair of dark-wash denim with a cotton tee and a good-quality zip-up sweater. Don’t forget to spice it up with accessories, like a watch or bracelet.

3. The Cultured Date


 Cultured Date Wear  Shoes for Cultured Date

If you want to go out for Valentine’s Day but don’t want to spend the night battling the crowds for a table at an expensive restaurant, you can opt for tickets to a show, instead. Check out what comedy shows, concerts, or plays are going on in your city. This is a really fun date idea if you’re looking to add a little culture to your night. Of course, it’s best for couples who already know each other well, since you may not be able to do much talking during the show.

This is the perfect opportunity to throw on those suit separates you’ve got stashed in the back of your closet. Layer a sport coat over a button-down or sweater, and complete the look with a pair of high-quality jeans. You can elevate the look with dress shoes, or make it more playful with sneakers depending on where you’re headed.

4. The Busy Couple’s Coffee Date


 Busy Coffee Date  

If you’re still in the early stages of seeing someone, you might want to keep things more casual with a daytime coffee date. To help distinguish this date as something more memorable than your average weekday meetup, aim to choose a bakery or coffee shop with higher-end pastries. Adding a sweet treat to the date can help make it feel a bit more special without being overwhelming.

Even with the more casual setting, you still want to look good. Go for a wool and cashmere blend turtleneck, chinos, and a pair of Chelsea boots. If it’s cold out, feel free to pop on a peacoat or add a motorcycle jacket for an edgier look.

5. The Day Date


 Day Date Shirt  Day Date Jacket

If you’ve got the day off, you might treat your date to the finer things in life with a day date. Take them to see an art exhibit, a new museum, or their favorite animal at the zoo, if the weather permits. You could also have fun exploring neighboring cities and trying a new restaurant for lunch. These are the perfect activities to get the conversation flowing and spark some excitement over a new shared experience.

On a day date, you’ll want to wear layers as you go indoors and outdoors, maintaining a balance between dressy and casual wear. Pop a statement jacket over a nice polo and a pair of chinos. Keep things comfortable with a pair of clean sneakers.

 6. The Night Out Date

 Night Out Date  Night Out Date Pants


Treat your date to a night out on the town! Going out doesn’t necessarily mean hitting a packed club, although that could be a fun way to spend the night. You might also choose to head to your favorite low-key spot for a late-night bite to eat. Or, show your date your favorite neighborhood dive bar. Regardless of where you go, you’ll want to dress smart while still appearing casual and cool.

To strike this balance, go for a pair of black denim and black high-top sneakers to match. On top, choose from a slim-fit button-down or cotton t-shirt. Then, pop a motorcycle or denim jacket over it all, and don’t forget to accessorize with a hat.

Ultimately, Valentine’s Day is about the person you’re with - not the activity you do. Putting a little effort into your outfit goes a long way and can boost your confidence and impress your date. And remember, you can always head to Franky Fashion for the latest styles and outfit inspiration.

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