Shopping·13 min read

What I Would Wear for Valentine’s Day if I Had Somewhere Fabulous to Be

Design: theSkimm | Photos: Free People, Eloquii, Reformation
January 22, 2024

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This year, the fashion world seems to be saturated with Valentine’s Day spirit — from red sweaters to heart jewelry to girly bows — and uncharacteristically, I'm here for it. Maybe it’s because I’m still obsessed with all things red or because rom-coms are finally back in theaters, but love is quite literally in the air. So make some fabulous plans, grab the people who mean the most to you, and slip into a little something festive. Heart eyes all around.

Need Valentine's Day gift ideas? Check them out here.

Drinks Date


A Nice Top I’ll take in every color, please…

When one of our editors said this top was her favorite purchase of last year, I ordered it right away. She was right — it’s so flattering, I find myself reaching for it for every occasion. Whether you’re meeting someone new for a casual drink (kudos) or going to your spot with your partner, this top says “I just threw this on and I know it fits me perfectly.” You can’t go wrong with the black or red. ($68, Reformation)

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Abercrombie & Fitch

The Abercrombie & Fitch jeans I like better than my designer pairs…

I said what I said. The rise, the leg, the 20-plus washes to choose from…these Abercrombie jeans are that girl. They’ll hug your curves without feeling restricting and come in extended sizes and lengths. Pair them with the top above for a laidback sexy look. ($90, Abercrombie & Fitch)

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A leather blazer that makes any outfit instantly cool…

You’re going to need some type of outerwear, so why not make it a leather blazer you can wear 300 days out of the year? I’m obsessed with this one that’s made with buttery soft deadstock leather to eliminate unnecessary waste. With the relaxed fit, you can wear it with anything. ($375, Madewell)

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Dia & Co.

A classic blazer for a pop of pink…

As someone who saw the Barbie movie three times, don’t think I forgot about pink. This blazer is a whole outfit in itself and pairs with your favorite jeans seamlessly. I like that it has an open front and is slightly oversized, making it easily layerable over a T-shirt or sweater. ($229, Dia & Co.)

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The only ankle boot you’ll ever need…

I bought these on a spendy whim when my previous ankle boots were so ground down I was practically walking on the street (not exaggerating). So while I know they’re pricey, they really are the perfect ankle boot. The heel is not too high for everyday wear, the pointed toe is timeless and looks great peeking out of pants, and they’re just so comfortable. Treat yourself ahead of the holiday to complete your ’fit. ($395, Staud)

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Fancy Dinner


An investment dress you’ll wear for years…

This dress deserves a night on the town. It has a chic high neck, straps that cross in the back with a cutout, and ruching on the sides to accentuate your waist. You’ll feel like a million bucks and find yourself stopping to appreciate how good you look in the mirror. Wear this to a wedding later to wow again. ($298, Reformation)

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A dress that had me at the bows…

I saw this on Instagram and could not stop thinking about it. From the bow details to the open back to the long sleeves (which’ll actually keep you warm), I can’t think of anything I’d rather wear out to dinner. Add minimal accessories to keep the dress as the focal point or really lean in and style your hair with these mini red bows. ($269, Nordstrom)

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A sweater dress that’ll keep you comfortable…

If you’re leaving the house but want to keep cozy, may I suggest this adorable blush-colored sweater dress? It’s low-key sexy, as most sweater dresses are, but you’ll basically feel like you’re wearing pajamas. The best part: the gold heart buttons. ($65.97, Eloquii)

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Astrid & Miyu

Heart earrings that aren’t kitschy…

Take your dinner outfit a step further by adorning your ears with these and wearing a slicked-back bun. They’re stunning in person, and they come off way more elegant than kitschy. Not that there’s anything wrong with that. In the words of Kate Winslet in The Holiday, “I’m looking for corny in my life.” ($130, Astrid & Miyu)

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A slingback pump that’s too cute to pass up…

Just give me a few bows and a pointed toe and I’m there. Whether you get these in the black for practicality or the red to stay on theme, they’ll top off your fancy dinner outfit and become one of your favorite pairs to wear every day after that. The ankle strap gives you enough stability to walk confidently from the restaurant to after-dinner cocktails. ($298, Reformation)

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Cozy Night In


A crewneck sweatshirt that needs no introduction…

Skims always knocks it out of the park with their loungewear. This cotton fleece sweatshirt is incredibly soft with a lived-in feel, and the slightly cropped length works with any kind of bottoms. The baby pink brings some romance to a Valentine’s Day movie night. The matching joggers are a must. ($68, Skims)

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A pajama set by the best pajama brand of all time…

I’ve talked about my love for P.J. Salvage pajamas before, so you know I had to include one of their Valentine’s Day-ready sets. I love that the top is really more like a sweatshirt, so you can layer it over a shirt, and the joggers aren’t too tight. The polka-dot-and-hearts combo is a subtle pattern you’ll want to wear all year. ($128, Bloomingdale’s)

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A lace trim tank ideal for Netflix and chill…

This tank is what you want that special someone to think you hang around the house in (when in reality it’s a giant intramural sports T-shirt from college). The lace trim nods to sexiness, but the conversation heart pattern keeps things playful. Grab the matching shorts to complete your outfit. ($20.21, Aerie)

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Urban Outfitters

The pair of Uggs I can’t live without…

I will probably be wearing these ultra-mini Uggs for the rest of my life. They’re the best slippers, coffee-run shoes, and foot warmers ever. The inside is so plush and the ankle height makes them easy to pull on. How cute would the pink ones be to top off your Valentine’s Day staying-in outfit? ($150, Urban Outfitters)

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Girls Night Out

Free People

A flower-adorned tube top that’s unexpected…

Welcome to the most fabulous kind of Valentine’s Day plans: the Girls Night Out. It’s the best opportunity to lean into the girly aesthetic, in my opinion, like this rosette tube top that reads as festive and fun in any color you choose. It’ll fit you like a glove and won’t require a strapless bra. Huge win. ($128, Free People)

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A black patent skirt you’ll wonder how you ever lived without…

Pull on this faux leather mini with your flower tube top to give your outfit a little edginess. It has silver hardware on the front, and the high-shine patent material is so eye-catching. Take it out on the town, then wear it to the office with a turtleneck and tights. ($198, Revolve)

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Free People

A mini dress with ‘80s prom vibes…

With a modern twist. From the drop waist to the pleated middle to the flared skirt, every detail is more perfect than the last. I love the gathering at the bust and the fact that the deep pink is a little more interesting than the typical Valentine’s Day shade. Carrie Bradshaw would approve. ($250, Free People)

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A sexy satin number…

This is how you do grown-up sexy with your girls. This satin midi has a thigh-baring slit, plus a playful twist at the bust with a cutout. An open collar and bell sleeves offer unexpected polish that’s still very club-appropriate. ($72.90, Rebdolls)

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A pair of investment boots you won’t regret buying…

If Taylor Swift is wearing heeled boots out to dinner with her friends, I’m wearing heeled boots out to dinner with my friends. These will never go out of style, since they’re knee height with a practical block heel. They’ll look good with skirts, dresses, over jeans, you name it. ($695, Shopbop)

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What to Wear Underneath


A red thong with a dazzling detail…

This thong hits the right note of tasteful Valentine’s Day lingerie, thanks to the fiery red shade and crystals on the back. Grab the matching teddy to treat yourself and your lingerie drawer to an upgrade. ($78, Revolve)

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A balconette bra that looks way more expensive than it is…

This unlined balconette bra has pretty lace detailing, but it’s supportive and comfortable enough to wear every day, according to its 1,000-plus five-star reviews. It also comes in black, if red lingerie isn’t your thing. ($17, Target)

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A breathable bra-and-panties set that’s incredibly comfortable…

This popular set seriously feels like wearing nothing, courtesy of the cooling, lightweight mesh material. The bralette will still provide enough lift under your Nice Top or dress, even without an underwire. The matching brief in the red floral print is the icing on top. ($63, EBY)

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Victoria's Secret

A satin slip you’ll wear more than you think…

Is there anything that screams Valentine’s Day more than Victoria’s Secret? This slip is a classic style with a V-neck, criss-cross straps, and a low back, and is very discreet when worn under your outfit. I love that it has adjustable straps so you can ensure a proper fit, and it’s soft enough to sleep in when you get home from your plans. Now that’s fabulous. ($69.95, Victoria’s Secret)

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