9 Valentine’s Day Date Ideas (And What You Should Wear)

A cute outfit for an active Valentine's Day Date

Now that we’ve all recovered from Christmas (well, for the most part), it is time to move onto the next holiday. Valentine’s Day is only three weeks away. To be clear, I don’t view Valentine’s Day as a mini Christmas. Big Valentine’s Day gifts are completely unnecessary, but it is a good excuse to spend some time with the one you love. To me, there is nothing wrong with wearing a cute outfit on a fun-filled Valentine’s Day.

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Since I love to be prepared, I came up with a few of my favorite ideas for a memorable Valentine’s Day. Kurt and I have had some amazing Valentine’s Day dates together over the years. We’ve also had years where we’ve chosen to spend it at home (likely because of the lack of a babysitter). Whatever the type of date you choose, I hope a few of our date ideas will be useful for some of you guys.

  1. Dinner and a movie. Yes, let’s start with the most obvious date choice. The reason it is so popular is because you can’t go wrong with choosing a good meal and a new blockbuster. Typically movie tickets don’t sell out weeks in advance, and if you choose restaurants that are a tad off the beaten path, you shouldn’t have a hard time getting a table. Or even plan a lunch date and a matinee to avoid the crowds.
  2. Plan a staycation. No need to spend extra money on a flight, just book a night or two at a local resort or hotel. There is nothing more fun than getting dressed up, grabbing a drink at a hotel bar and heading out to a fancy (or not-so-fancy) dinner. Sleeping in a giant comfy bed with a million pillows will make you feel like you are on vacation, even if it is just for a night.
  3. Be active together. This is a personal favorite for me and my hubs. We love to chat while clocking a few miles hiking on a mountain or playing around at an indoor rock climbing facility. The mountains typically don’t require reservations. Plus then I don’t feel bad indulging in a Valentine’s Day dessert after burning off a few calories.
  4. Go skydiving (with or without a plane). My husband is dying to go skydiving; however, there is no way you could pay me to jump out of a plane. Yes, you can choose to do the real deal, but I personally recommend the indoor skydiving route instead. I’ve now done it twice at iFly and it is was a blast. Because there is no jumping, it isn’t scary at all and it will make for a memorable date.
  5. Stay home and cook a special meal. Like I said, I’ve spent a number of Valentine’s Day dates at home. Even if you choose to avoid the crowds, it doesn’t mean staying home can’t be special. Cook a special meal together, set up the table and use your fancy china to eat by candle light. Even get dressed up! No reason staying home can’t be a ton of fun.
  6. Buy concert or show tickets. Check out the Ticketmaster website and see what concerts and shows are going on in your town around Valentine’s Day. Since Valentine’s Day is on a Wednesday this year, we all have the benefit of choosing either the weekend before or after to celebrate. As an added bonus, surprise your significant other with the tickets. Your date and gift is all taken care of in one fell swoop.
  7. Get creative. I feel like everywhere I go, I see signs for those painting party places. I’ve actually never done one (no good reason why), but book a reservation and take your man along. Since my husband and I love a little competition, see who is the best painter. Or I’ve even seen places (like Pinspiration in Phoenix) where you can have a splatter paint date, complete with champagne. I’m all about messy and memorable fun.
  8. Plan a spa day. If money wasn’t an object, this would be my go-to Valentine’s Day date every single year. Book a couples massage and enjoy a glass of champagne relaxing in the hot tub afterwards. It doesn’t get much better than that.
  9. Go golfing. I know this would be my husband’s #1 date idea. Whether it is a real course or indoor option, this idea will definitely be a hit for a lot of guys. Even if you are in a cold weather location and can’t hit the links, try an indoor driving range or even mini golf. Places like Top Golf even serve dinner!

Don’t forget to check Groupon or Travelzoo to find deals on attractions in your area. Gotta love a bargain.

Now, what to wear. Since I’m all about dressing for the occasion, I’ve put together a couple different types of outfit ideas. Everything from cute and casual to dressy and sexy.

Outfit idea #1: Cute and casual. Whether you are heading out to a movie, going for a hike or cooking dinner at home, there is no reason you can’t look cute while being comfortable. There is a good chance I’ll be wearing my favorite leggings, slip on sneakers, a cute sweater and a puffy vest this Valentine’s Day.

 

Love this outfit for a casual Valentine's Day

I love a good casual Valentine's Day

Such a cute vest for Valentine's Day

Outfit idea #2: A cardigan and tall boots. I personally love this option because cardigans are typically comfortable, but you can add a hint of lace underneath to dress it up a bit. My red cardigan is old, but this one is similar. I can’t say enough good things about my silk and lace cami (p.s. the back is adorable), jeans, boots, and initial necklace. Perfect look for a day date into night.

Valentine' Day sweater

A casual sweater perfect for Valentine's Day

Love this casual red sweater

Outfit idea #3: Pretty in pink. I’ll admit, I’m usually drawn to festive colors. When I think of Valentine’s Day, I always think of red or pink. My exact pink sweater is sold out, but this cardigan is really similar. I also love the mix of the distressed jeans and booties to bring the whole look together. Perfect look for a concert or painting date if I do say so myself.This soft sweater would be perfect for Valentine's Day

Outfit idea #4: Jeans and a flowy off the shoulder top. A red off the shoulder top (try this one or this one) the perfect shirt for Valentine’s Day. This look would be ideal for a trendy restaurant or a night out on the town. Add a black leather jacket on top to give it a chic look.

Cute and sexy top for Valentine's Day

The perfect top for Valentine's Day

Love this red hot top for Valentine's Day

Outfit idea #5: Wear an amazing red dress. You guys saw this red lace dress on me before the holidays. It was perfect for a Christmas party and it is even better for Valentine’s Day. It fits true-to-size and the long sleeves are ideal for those cool winter nights. And better yet, it is only $60! Nothing says Valentine’s Day quite like lace.

 The perfect red dress for Valentine's Day

Love this red lace dress for Valentine's Day

Whew, that was a long one. For those of you who made it this far, I hope this helps you prepare for Valentine’s Day. Is anyone looking for gift ideas, or should we all agree to do cards only this year? Let me know in the comments below!

Jenny

19 Comments

  1. I’m with you on “Go active together”! It is such a fun way to celebrate V. Day! And I love look #3!!!
    ~ xo Sheree
    Posh Classy Mom

  2. These are all such great ideas for Valentine’s Day. Being a mom and having three kids it is hard to plan a special day but these tips are easy and perfect to do with the whole family or even for an evening out with the hubbie. I love all your outfit choices and that dress with the lace is so pretty. I like the idea of going outdoors maybe with the whole family and then spending the evening with my hubbie. Thanks for all these ideas! xoxo, Christine
    http://dailykongfidence.com/

  3. What great date ideas! I have never done indoor skydiving before, sounds so much fun! I need to look into this for sure!

  4. So many adorable looks for Valentine’s day, now matter how you choose to celebrate it. I love your ideas for how to spend the day together too!

  5. I love all your sate ideas!! We did the sky diving together a few years ago and loved doing that! I wouldn’t have thought about it as a date idea but it would be super fun to do it like that!

  6. Hey Darling
    How are you?
    Love the Valentines Day Looks and Idea:)
    Each looks are so Sweet, I can’t decide which one is my Favorite:)
    Kisses Hugs
    Karina
    Happy Week

  7. I usually cook special dinner for my husband and we go out for romantic walk or watch some tv show together. This year, I am thinking to travel somewhere 😉
    But thanks for inspo!

  8. Plan a SPA day or play gold these are my two favourite activities, but for Valentine’s Day I think we’re going to the restaurant and pretend to be normal just for one day, haha. And afterwards get creative and go crazy 🙂 Thanks for sharing these amazing tips.

    Cheers, Eliza | http://www.fashion-confession.com

  9. Hi love,

    Thank you for this list. I will save it and get some ideas. I’m truly excited for Valentines and can’t wait to spend it with my beloved person. By the way, all your looks are super stylish and feminine!

    xoxo
    Darya

  10. You shared some really great Valentine’s looks here and I am definitely inspired! You also gave me an idea to plan a staycation rather than trying to go somewhere. It makes it so much easier, making it actually feel like vacation than being at home. Spa day sounds nice too! 🙂

    http://www.thebeautybeau.com

  11. Last vday we went to hiking with my hubby! I really like that, It was so much relaxing and spending most quality time ! This year we are planing to go spa, I will probably wear yoga pants.

    Thank you for ideas
    xx
    Sirin

  12. So much darling Valentine’s Day inspiration here!!! Love all of your looks. The date night ideas are gold! The staycation is such a fun idea and the skydiving, too!

    xoxo,
    Rach

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