14 Days of Valentine’s Outfits: A New Tradition That’ll Melt Your Heart

Valentine’s Day isn’t just about chocolate and roses (although let’s be honest, those help).

It’s about love—big, messy, unconditional love that’s spilled juice cups, crayon masterpieces, and the fifth “Mom, watch this!” of the day.

This year, why not take that love to the next level with a new tradition that’ll make your heart swell—and your kids look adorable: 14 days of Valentine’s outfits leading up to February 14th. It’s like an advent calendar, but instead of tiny chocolates, you get tiny humans dressed in heart-covered perfection.

Grab your tissues (and maybe a latte), because this tradition is equal parts sweet, sentimental, and totally Instagram-worthy.

Step 1: Pick the Pieces

Start with a mix of festive staples that can be styled multiple ways. Think red and pink smocked dresses, graphic tees with “XO” designs, and accessories so cute you’ll wish they came in your size. The trick is to choose versatile items that work for playdates, school drop-offs, or impromptu kitchen dance parties.

Need inspiration? Our Valentine’s collection has everything from “aww” to “OMG, I need this NOW.” (Because we’re here to help you win Valentine’s.)

Pro Tip: When your 3-year-old insists on wearing a pajama top with a tutu, let it happen. Confidence is always in season.

Step 2: Add a Little Magic

Each morning, reveal your child’s outfit with a small surprise—a sweet note tucked into their lunchbox, a tiny heart-shaped cookie, or just an over-the-top, “You’re going to be the cutest little Valentine at school today!”

Imagine your kids running into the kitchen, giggling at their heart-covered socks and twirling in their red-and-pink outfits like they’re the stars of their own rom-com. It’s pure, unfiltered childhood joy—and you’re the director.

(Also, yes, they’ll probably spill something on that cute outfit by 9 a.m. It’s fine. This is why we do laundry in bulk.)

Step 3: Tie in Memories

Make each day’s outfit part of a bigger family moment. Maybe they wear a red sweater while baking heart-shaped cookies with you. Or a pink dress while they write Valentine’s cards for their grandparents. Or festive pajamas during your family’s annual viewing of Be My Valentine, Charlie Brown.

By February 14th, it’s not just about the clothes. It’s about the moments. The laughter, the sticky frosting hands, the way your little one looked at you and said, “I made this just for you, Mommy.”

Step 4: Embrace the Chaos

Look, not every morning will be Hallmark-card perfect. Some days, your kid will outright refuse the outfit you lovingly picked out because “hearts are for babies” or “I wanted the dinosaur shirt!” That’s okay. Let them wear the dino shirt with heart pants. Or layer the heart dress over the dino tee. Love isn’t perfect, and neither are outfits.

It’s not about looking picture-perfect. It’s about being together and creating something special.

Step 5: Document the Sweetness

Take a photo each day—messy hair, mismatched socks, yogurt spills, and all. By Valentine’s Day, you’ll have 14 days’ worth of memories captured forever. Someday, you’ll look back at these pictures and wonder where the time went. How did they go from tiny twirls to school dances to, gulp, driving?

And those outfits, the ones you carefully picked out for them, will become more than clothes. They’ll be little time capsules of their childhood, wrapped in love.

Be sure to tag us in your photos featuring our outfits—we absolutely love seeing your little ones dressed in Annie and Addie!

Why This Tradition Matters

Let’s face it—time moves too fast. One minute, your baby’s in your arms, and the next, they’re borrowing your car keys (and your favorite hoodie). Traditions like this one slow the clock, even for a moment.

It’s not just about cute outfits (although, come on, who doesn’t love a smocked dress with hearts?). It’s about celebrating the little things: their laughter, their joy, the way they light up when you tell them how much you love them.

So this Valentine’s season, start a tradition that makes them feel special every single day. Because if love is in the details, then 14 days of Valentine’s outfits is one of the sweetest ways to say, “You’re my forever Valentine.”

Ready to start your new tradition? Browse our Valentine’s collection for outfits your kids will love—and you’ll treasure.

What’s your favorite way to celebrate Valentine’s Day with your little ones? Share your ideas below—let’s spread the love!