Valentine’s Day Date Ideas + What to Wear on Them

Kasey Goedeker of Running in Heels wears a red trapeze dress downtown dallas. Photo by Jeff Dietz

With Valentine’s Day looming and dates to be planned, I am sharing some of the best ideas for dates and my favorite outfits to wear for them. I crowd-sourced a few of the below ideas via Instagram from you all and decided to compile them here with outfits! Everything below can be worn for a Valentine’s Day date or year round! From cocktail to casual, I’ve got options for every occasion!
​​​​​​​Kale and I always default to a dinner date, so when I asked for ideas, I was looking for more than just dinner. I was so happy because you all delivered with great options! I also added in a few of my own ideas so I hope you find this helpful! Keep reading because I’m sharing all of the ideas and outfits to go with them below.

PS check out my friend Casey’s blog post with even more great options!

Casual Valentine’s Date

Casual Date Ideas

  • Movies: Any movie just won’t cut it for Valentine’s Day. Alamo Drafthouse is so much fun and a great option. You can order your meal and drinks while you watch. Yes, the food is actually great! Another idea, if it isn’t too cold is a drive-in movie! I haven’t been to a drive-in in ages, but I would absolutely love this! *hint hint*
  • An Escape Room: This was a recommendation from my question box on Instagram! I’ve never done one, but on one hand my self-diagnosed acute cleithrophobia (fear of being trapped) tells me I wouldn’t love it. Though, on the other hand, it does seem like a really fun idea with a few friends! I’m torn, but I think I could be convinced to try it.
  • Go to the Zoo/Aquarium/Museum: This time of year, you’ll most likely be basing your choice off of the weather, but these are all such great ideas to just spend time together. While there are tons of things to look at in these places, the best part is walking around together and taking your time. *PS the Dallas Arboretum has $5 admission until Feb 22!
  • Valentine’s Day Wine Walk: Wine? I’m there. A wine walk is usually in a neighborhood or street of your town where all of the businesses open their doors and serve wine! You pay a small fee for a glass and wander around to each store or gallery to fill up your glass! Try this one in Dallas!

For a casual V-day look, I’m choosing this adorable cream colored sweater with embroidered hearts! It is very obviously Valentine’s Day, which I typically stay away from. I do think this one is understated enough, so I went for it. I paired it with my (old) burgundy faux leather skirt for a fun edgy look. If you’re doing one of the activities I mentioned above, you may want to swap the skirt for jeans or even joggers for a fun, more comfortable alternative.

Dressed-Up Valentine’s Day Date

Dressed-Up Date Ideas

  • Dinner Date: Our favorite places to go for a nice occasion in Dallas are Nobu, Five Sixty in Reunion Tower, Nick and Sam’s, Nick and Sam’s Grill, and Dallas Fish Market.
  • Cocktail Hour: Bar hop and try some fun cocktail spots! Try a few different or new bars around town. Deep Ellum in Dallas has a ton a great spots like HIDE, Black Swan Saloon, and Harlowe MXM all super close by. No cars necessary!
  • Apps & Dessert: Grab appetizers and dessert, no dinner. Whenever we go to dinner, I end up eating too much, feeling too full for dessert. I used to do this with my mom and sister when we wanted to try out the dessert menu!
  • Cooking Class: To be completely honest, I’ve never done this one either, but it was highly recommended from my Instagram question box! I’m placing it here because I have no idea what you’d actually wear to a cooking class but I can tell you, I’d probably overdress.

The dressed-up in between type of looks are usually my favorite. I absolutely love this fun tulle skirt and am trying out this adorable Carrie Bradshaw look with it! The top is a sweater, so it’s definitely seasonally appropriate! The second look is this neutral bodycon dress. It’s got a gorgeous open back and I paired it with black accessories including a black moto jacket for an edgier look, just in case you aren’t into the cliche pink and red on Valentine’s Day.

Cocktail or Formal Valentine’s Date

Cocktail/Formal Valentine’s Day Date Ideas

  • Try a set menu: This is something we’ve never done, I’d be willing to bet some of the places I listed above may have set menus on Valentine’s Day, we’ve just missed them. You can check on Eventbrite to see restaurants that have their events listed there.
  • Murder Mystery Gala: This event looks like a blast. I’d love to do a murder mystery dinner party and this one is a huge event and highly organized. It’s their 29th annual gala, so you know they know what they’re doing! Plus it’s not too expensive. Just around $120/person and group discounts are available.

I used to dream about super fancy Valentine’s Day dates, but now I’m so much happier just knowing I have someone amazing to celebrate with! Still, one of these days I’m going to convince Kale to go to a masquerade ball and it’s going to be amazing. (If you’re going to a masquerade ball, check out the gown in this post.) I’m not going to suggest anything that extravagant, especially since Valentine’s Day is a mere two weeks away at this point. The outfits below are more cocktail appropriate.

Starting with this amazing jumpsuit (also note: no red or pink tones) with an open back. I ordered a S and it’s a little big on me, and definitely long, so order asap if you think you might need it altered. Mine were hemmed about 2.5in and I’m 5’5″ and wore it with heels. My burgundy dress is one of my favorites! I’ve gotten great use out of it since I bought it for the wedding we attended in October! It’s still available and comes in a lighter pink color as well! Finally, the red trapeze dress. Can you tell I love pleats? I couldn’t resist this one. I chose my normal size, xs, but if you have broad shoulders, size up.

Leave a Comment


  1. Brooke wrote:

    Love these Valentine’s Day date ideas! Now I just gotta find me a man! 😉

    Posted 1.31.19 Reply
  2. These are all cute looks! I love the different date ideas, something for everyone to do!

    Posted 1.31.19 Reply
  3. Cathy wrote:

    So many cute outfits! I love that red dress, it’s fabulous!!


    Posted 1.31.19 Reply
  4. Liz wrote:

    That first photo is gorgeous!! I love all these outfits and date ideas ( I want to do them all lol!)>

    Posted 1.31.19 Reply
  5. Em wrote:

    so many cute outfits and date night ideas!

    Posted 1.31.19 Reply
  6. Greta wrote:

    So many fun valentine’s day ideas! My hubby and I are going to a hockey game this year.

    Posted 1.31.19 Reply
  7. ashley hargrove wrote:

    That red dress shot is STUNNING!! One of my favorites of yours!! I love all of these looks too but I think I’m going to be wearing my PJs on Valentine’s Day! OR that black sweater with little hearts that you posted in white!! 😉

    Posted 1.31.19 Reply
  8. Morgan wrote:

    I will most likely be spending the holiday in my heart pj’s but I love all your dressy outfits! That black jumpsuit it so pretty!

    How 2 Wear It []

    Posted 2.1.19 Reply
  9. Deanie wrote:

    This is such a great post idea, to match the looks with date ideas!
    Xo, Deanie
    Deanie Michelle

    Posted 2.1.19 Reply
  10. adriana wrote:

    These are all such fun picks! Love that dress on you!

    Posted 2.4.19 Reply
  11. i would love to try an escape room but all these scary movies freak me out!

    Posted 2.4.19 Reply
  12. Kristina wrote:

    I loveee escape rooms, such a great idea! This year I’m taking my hubby to a cooking class, something we’ve never done before!

    Posted 2.7.19 Reply
  13. Chloe wrote:

    That red dress picture of you is amazing!!! And love these outfits!!

    Posted 2.12.19 Reply
  14. These are such cute looks!

    Posted 2.14.19 Reply
  15. OMG…I just love your dresses <3 Love the way you click the pictures.

    Posted 3.7.19 Reply