10 Head-to-Toe Date Night Outfit Ideas for Valentine's Day (2024)

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Whatever your plans on Valentine’s Day, it’s fun to get yourself dressed and out of the house. If you’re not quite sure what to wear– or if you’re just looking for some cute and affordable new fashion finds, I’ve got you covered in today’s post. Keep reading for 10 head-to-toe Valentine’s Day date night outfit ideas!

1. Red Tie Waist Sweater Pencil Dress

If you want a date night outfit that feels like a nightgown, this tie waist sweater dress is a winner! I actually bought it for Christmas and ended up re-wearing it again for Galentine’s festivities. It’s super comfy, ultra slimming (gotta love tie waists!), and under $40. It comes in over a dozen colors, too, including a really pretty light pink that’s perfect for spring weddings!

Click to Shop: Red Tie Waist Sweater Dress | Red Block Heel Sandals | Gold Smile Pendant Necklace (Kyle bought me the Tiffany version, so I’m linking an uber affordable version under $10) | Large Pearl Stud Earrings

Also, if your dog is your date, stay tuned for a post on how to make your own dog bows!

2. Red Stripe Colorblock Sweater

I fell in love with this cozy red stripe colorblock sweater the second I saw it. It’s literally perfect for Valentine’s Day (I mean, it’s pink, red, and white all in one sweater) and looks adorable paired with red Hunter boots! If you love the sweater but aren’t a fan of the red stripe, it also comes in pink stripe and yellow stripe, too.

3. White Pom Pom Sweater

I mentioned this pom pom sweater in January’s Things I Loved round-up (and featured it in this Galentine’s Day decor post)– and I’m not kidding when I say it’s the cutest sweater ever. Like ever. It’s also super warm, comes in gray, white, and pink, and has fun lantern sleeves!

Click to Shop: White Pom Pom Sweater | Pink Mini Skirt (old from Banana Republic, linking similar affordable style) | Pink Pearl Block Heel Sandals | Large Pearl Stud Earrings

4. Pink Ribbed Jumpsuit

This pink ribbed jumpsuit feels like pajamas and looks absolutely amazing in person! Not only is it a great date night outfit, it’s made of stretchy jersey material (ie. comfy as all get-out) and is perfect for holiday parties, baby showers, spring weddings, and just about every occasion in between. It also comes in red and black, too!

Click to Shop: Pink Short Sleeve Jumpsuit | Nude Block Heel Sandals | Gray Crossbody Bag | Silver Drop Statement Earrings (old from Kendra Scott, linking similar affordable style)

5. Pink Chino Pants

These pink Old Navy chinos, which are unfortunately no longer available (I found a similar style from J.Crew Factory, though!), were one of my favorite purchases of 2019. They’re just so darn cute, and I love that you can dress them up with a cami and blazer for date night or down with a white tee and sneakers for a casual girls’ night in!

Click to Shop: White Scalloped Cami | Pink Chino Pants (old from Old Navy, linking a similar affordable style) | Nude Wedge Sandals (old from Steve Madden, linking similar affordable style) | Pink Tote Bag (old from Walmart, linking similar affordable style)

6. Pink Midi Skirt

This pink pleated maxi skirt was practically made for romantic date nights (and maybe twirling, too). It’s so fun and flowy and looks amazing paired with both crop tops and button downs. See it styled both ways here!

Click to Shop: White Lace Crop Top | Pink Pleated Midi Skirt | Pink Dress Pumps | Ring Crossbody Bag

7. Red Lace Midi Dress

I feel like a princess every time I put on this red lace midi dress! The eyelet lace overlay is just so feminine and delicate. It comes in a handful of colors, too, and makes a super cute date night outfit and budget-friendly wedding guest outfit.

Click to Shop: Red Lace Midi Dress | Black Bow Sandals (old from Nina Shoes, linked similar style with rhinestone-studded ankle strap) | Black Lace Clutch | Crystal Statement Earrings

8. Collared Shirt/Colorblock Sweater Combo

If you want to go casual this Valentine’s/Galentine’s Day, I love this classic crewneck sweater/button down combo! Jeans might be a little too relaxed for fancier spots, but you could easily swap them for a pencil skirt or white wide-leg pants to posh-up the outfit a little bit!

Click to Shop: Pink and Red Colorblock Sweater (old from Old Navy, linking similar affordable style) | Relaxed White Oxford | White Distressed Skinny Jeans | Nude Pumps (they’re uber pricey but the one shoe brand I’ll actually splurge on– linking a more affordable style here, though) | Gold Mini Hoop Earrings

9. Red Pleated Bow Skirt

I own this pleated bow skirt in both pink and red and can’t say enough good things about it. It looks and feels like a $200 Kate Spade skirt and has a $30 price tag. It comes in a handful of cute colors, too, including gold! See it styled for the holidays here.

Click to Shop: White Wrap Top | Red Pleated Bow Midi Skirt | Red Block Heel Sandals | Gold Mini Hoop Earrings

10. Relaxed Pink Button Down

One of my all-time favorite date night outfit ideas is a relaxed pink button down paired with girlfriend jeans and block heel sandals. It’s comfy, easy, and festive! Check out the full outfit post here.

Click to Shop: Vintage Destructed Girlfriend Jeans(these are the Vintage Destructed wash, and they run large– I’m wearing a 0/25)|Pink Striped Button Down(wearing a Small)|Nude Block Heel Sandals|Gold Statement Earrings|Pink Resin Apple Watch Band(mine is called Pink Texture) |Rose Gold Cuff Bracelet|Gold Smile Pendant Necklace

So, which of these Valentine’s Day date night outfit ideas is your favorite? Do you like to go more casual or dress up? I’m more of a dress up kind of girl myself, but let’s be honest– Kyle and I will most likely order stuffed crust pizza from Pizza Hut, drink champagne, and watch Netflix at home again. It’s become our little tradition, which we started to avoid the Valentine’s Day dinner crowd a few years back. Now I genuinely look forward to it every year!

For more of my favorite pink and red co*cktail dresses under $50, click here. Thanks so much for reading, y’all!

Photography by Catherine Rhodes.