Shopping·9 min read

Valentine’s Day Outfits That Are Not Too Much, Not Too Little, but Just Right

valentines-day-outfits-date-outfits
Design: theSkimm | Photos: Free People, Quince, Anthropologie
January 30, 2026

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Valentine’s Day is approaching, and we say it’s okay to celebrate however and with whomever you want — your partner, your best friends, or yourself. Whether you’re decked out in pinks, reds, and hearts, or you’re looking for a more subtle nod to the holiday, these outfits are just right.

For more Valentine’s Day gifts, click here.

button-up-shirt
Anthropologie

A button-up shirt that says it all…

If you’d like your outfit to do the talking, this button-up is subtly embroidered with “I love you” on the pocket and the hem. It’s slightly cropped so it’ll pair nicely with your favorite pair of high-rise jeans. ($118, Anthropologie)

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maxi-dress
Quince

A maxi dress that’ll keep you comfortable all night…

This sleek maxi is made of soft and stretchy organic cotton, so whether you’re enjoying a four-course tasting menu or dancing with your girls, you’ll feel good. The Wine Tasting Red is perfect for the occasion. ($60, Quince)

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pajama-set
Hill House Home

A fresh pajama set with hearts all over…

If you’re spending the night watching Tell Me Lies (just us?), you deserve a new pajama set. It has pink hearts all over and cute details like a ruched waist and ruffles on the collar. We can’t think of a better way to show yourself some love. ($128, Hill House Home)

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knix
Knix

A push-up bra that feels like wearing nothing…

Yes, you read that right. Unlike the push-up bras of your teenage years, this one is wire-free, so nothing is digging in as the foam cups give you a little lift. It won’t show, even under the tightest of tees, and the cherry red is particularly alluring. ($68, Knix)

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silk-dress
Reformation

A silk dress you’ll never get tired of…

Invest in this classic silk dress that’ll become your new wardrobe staple. You can layer a turtleneck underneath for a chic dinner date vibe or throw on a heart necklace to lean into the holiday. You’ll wear it to a spring wedding in a few months. ($248, Reformation)

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satin-shorts
Free People

A pair of satin shorts you can wear to stay in or go out…

Slip these on to make a movie night feel special, or if you’re hitting the town, layer them over tights with a chunky sweater. You’ll wear the pink or red ones even after the holiday is over. ($50, Free People)

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cardigan
Quince

A cashmere cardigan that looks more expensive than it is…

You can’t beat the look of a perfect-fitting cardigan. It’s sleek, festive in the red, and this one won’t cost you an arm and a leg. They also have a crewneck version we own and love. ($79.90, Quince)

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velvet-dress
Saks Fifth Avenue

A mixed-fabric dress that’s even better in person…

I wore this dress for Christmas dinner, and it fits even better than you can imagine. The V-neck is pretty but not so low that I felt uncomfortable or couldn’t wear a bra, and the slip-like skirt is body-skimming without being too clingy. I’ll be pulling it out for my Valentine’s Day plans, for sure. ($298, Saks Fifth Avenue)

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polo-sweater
Nordstrom

A polo sweater that’s pink and red done right…

Too often pink and red together come off as kitschy, but this polo sweater says otherwise. Maybe it’s the hint of brown worked into the striped pattern, or maybe it’s the retro style. Either way, Staud has knocked it out of the park again. ($175, Nordstrom)

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sweatshirt
Abercrombie & Fitch

A sweatshirt that’s a little more elevated…

If your Valentine’s Day consists of running errands — coffee, nails, and Target count — then hitting the couch, this mockneck crew is perfect for both. It comes in a cute pink color and has matching sweatpants. ($65, Abercrombie & Fitch)

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sweater
Revolve

A sweater to show a little skin…

There’s something so grown sexy about an off-the-shoulder top. Pair this one with leather pants and heels for an effortless date night ’fit. Since you’re essentially stepping out in a cozy sweater, you’ll be comfortable no matter your plans. ($97, Revolve)

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trousers
Gap

A pair of trousers that make a statement…

If a pink or red top is a little too on the nose for you, stand out by opting for a pair of red trousers. The possibilities are endless for what you can pair them with, from a white turtleneck to a blazer with just a bra underneath. ($71, Gap)

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polka-dot-dress
Urban Outfitters

A polka-dot maxi dress perfect for girls’ night…

Does this maxi dress have frills, polka dots, and a bow? Yes, yes, and yes. But somehow it still works without being too cheesy, especially if your plans involve a bottle of wine and your best friends. ($289, Urban Outfitters)

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lace-dress
Zara

A lace dress in an unconventional color…

I have this dress in black (it’s sold out), and when I bought it, I had no idea I would wear it so much. You can put a long-sleeve shirt underneath it to make it a little less revealing (and chilly). I love the idea of wearing chocolate brown instead of the typical colors. ($99.90, Zara)

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turtleneck
Old Navy

A classic turtleneck that’s always in style…

Whether you’re going on a first date or grabbing a casual burger with your partner, a turtleneck will never not be chic. Dress it up or down, but either way it’s giving, “I look impossibly put-together, even though I didn’t put much thought into it.” ($24.49, Old Navy)

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jersey-top
Nordstrom

A cheeky top you’ll want to wear all the time…

Not only is this waffle-knit long-sleeve comfy for lounging around the house, but you’ll also look cool wearing it out of the house since sportswear is trending. If you’re not the holiday’s biggest fan, this top will help you express it. ($110, Nordstrom)

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