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Valentine’s Day: Date Night Ideas & Outfits

Valentine's Day date night ideas and outfits to wear

Hey, there! Let’s talk Valentine’s Day. You know, that one night a year when you swap the leggings and top knot for something a little more glamorous (or at least clean). Whether you’re team “let’s go all out” or team “Netflix and chocolate”—we’ve got you covered with date night ideas and outfits that strike the perfect balance of festive and practical.

The "Fancy Restaurant" Dream Night


Picture this: you’re at a restaurant where no one has chicken nuggets on their plate, and your outfit is on point. This is the dream, right?


  • The Vibe: Sophisticated and sleek, but not so fussy you’re uncomfortable all night.

  • Outfit Pick: A satin top paired with your favorite jeans (that make your butt look amazing because you know, it’s Valentine’s Day). Add nude heels (or flats if you’re just not feeling it—no judgment!) and a gold necklace. Pro tip: a blazer or leather jacket - doubles as warmth and makes you look all badass.

Movie & Dessert Date (Because Dinner Is Overrated)


Ah, the sweet simplicity of a movie theater—no one is asking you for snacks every two minutes, and someone else made the popcorn.


  • The Vibe: Casual, cute, and comfy enough to devour a brownie sundae afterward.

  • Outfit Pick: A muted pink or mauve sweater to still say Valentine’s Day, but just a tamed down kind of night. Keep it simple with ankle boots and a crossbody bag so your hands are free for snacks (and you don’t have to put your purse on the floor at a movie theatre iykyk).

Wine Tasting: A Grown-Up Excuse to Sip Fancy Things


You’re swirling, sipping, and pretending you can taste those "notes of blackberry." (Don’t worry, no one actually knows what that means.)


  • The Vibe: Trendy but relaxed. You’re here to impress—but only slightly.

  • Outfit Pick: A patterned blouse paired with high-waisted jeans. Add strappy heels and maybe a small clutch. Bonus points for great makeup, cute hair and a swipe of perfume!

Ice Skating & Hot Cocoa: The "Let’s Be Cute and Active" Plan


Ice skating sounds romantic until you’re wobbling like Bambi. But hey, that’s part of the fun, right?


  • The Vibe: Cozy chic. You’ll look good on the ice and in the Instagram photos.

  • Outfit Pick: A pink checkered sweater is all you need to keep it festive, but also warm. Toss on a cute hat, gloves and a vest to make it a little extra! 

Cozy Night In (Because Babysitters Are Expensive)


Sometimes the best date night is one where you don’t even leave the house. Think comfy, but cute enough to remind your partner why they fell for you in the first place.


  • The Vibe: Relaxed but festive. You’re celebrating love and survival (because, honestly, parenthood is no joke).

  • Outfit Pick: A rose-colored lounge set, cozy socks and add a new blanket you can cuddle under. Bonus, a cute set is timeless in the cozy department so you’ll wear this one well into the rest of the year!

Whether you’re planning a big night out or a quiet evening in, Valentine’s Day is about celebrating love. No matter the plan, grab your partner and do something that you both enjoy. So, go ahead, pick the outfit, plan the date, and don’t forget to sneak some extra dessert.


Chat soon~ 🖤 CTB

Check out our entire Valentine's Collection online now! 

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