10 Comfortable (and Cute!) Valentine’s Day Outfit Ideas to Copy (2024)

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Love it or hate it, Valentine’s Day is coming—and if you haven’t already seen chocolate hearts and cheesy cards in every shop, buckle up. We all know in our heart of hearts that Valentine’s Day is a Hallmark holiday but listen: It’s the middle of February, winter is still raging it’s ugly head, Christmas is a distant hangover, and frankly, we need something to celebrate.

Even if you historically loathe the day of love, why not embrace it this year, no matter where you currently are in your love life. Whether you’re very single and ready to mingle or preparing to celebrate what seems like your 97th Valentine’s Day with the same partner, spice it up with what you wear! Below are a few Valentine’s Day outfit ideas suggestions depending on your current relationship status or date plans.

The First Valentine’s

The first Valentine’s day is always special: a bit of nerves, a bit of excitement or a bit of total shock if one member of the couple is completely unaware that they made plans on “the holiday.” I personally think it’s crucial not to go over the top here. Let’s hold on the red-heart tights and “I Love You” sweater and save that for the second Valentine’s Day (if you make it that far). I’d take a subtle yet festive approach and wear excellent-fitting jeans, a top with a pop of red or pink, and some fun accessories and dainty lingerie (for your own confidence boost, natch). This formula works for dinner in a chic restaurant, an at-home meal, or something off-piste like…bowling. (Note to self, if you are going bowling, choose your socks wisely, preferably ones without hearts on them…)

10 Comfortable (and Cute!) Valentine’s Day Outfit Ideas to Copy (1)

Sleeper

knitted cardigan

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Slvrlake

Grace high-rise wide-leg jeans

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Dôen

Idalia bra

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The Row

Cybil leather mules

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Valentino Garavani

Scoobie gold-tone earrings

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Nanushka

washed satin clutch

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Usisi Sister

Lena textured lace-up top

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Zara

TRF high rise wide leg jeans

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Reformation

mini rosetta shoulder bag

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Toteme

Mid Heel suede Chelsea boots

The Getaway

If you’re getting away from your daily life/habits/routine for Valentine’s Day then it’s also the time to dress away from your daily life. If you’re normally a jeans and top kinda gal but headed to the beach, try a charming dress or playsuit. If you’re planning a weekend trip to a nearby town or staycation in your own city where you tend to wear dresses to work, then go for a casual but polished combo with a knit and cool, corduroy trousers. The memo here is that whatever is normally “off limits” in your day to day—now is the time to embrace the opposite. Besides, traveling allows us to try on various versions of ourselves and what better way to do that than with your outfit?

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Missoni

Mare striped halterneck playsuit

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Zara

twisted cuff bracelet

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Hunza G

Maya cutout seersucker swimsuit

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Johanna Ortiz

A Certain Mystique pareo

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Rouje

Sebastien basket bag

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A.Emery

Jalen sandals

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&Daughter

Bansha Fair Isle cardigan

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Citizens of Humanity

Paloma cotton-blend corduroy wide-leg pants

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textured-leather belt

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M.Gemi

The Felize suede loafers

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Jil Sander

Tangle small leather cross-body bag

The Partner of Many Years

You know the saying—“You can’t teach an old dog new tricks but you can get an old dog new lingerie”? Ok, maybe that’s not the exact wording but it’s something along those lines, which I do think applies here. If your beloved partner has zero expectation for you to open the bedroom door in something beribboned and crotchless, a delicate cami set with a sweet lace trim is just the ticket. If it’s just you dining à deux on the couch and watching Netflix in your pajamas, upgrade that set to a silky pair to spice things up ever so slightly.

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La Perla

Maison embroidered camisole

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La Perla

Maison embroidered shorts

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Fleur du Mal

Rose and Vine embroidered lace balconette bra

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Fleur du Mal

Rose and Vine embroidered tulle briefs

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Eres

Angelo shirt

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Eres

Charme trousers

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Maison Margiela

feather mules

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Summer Fridays

Lip Butter balm

The Single and Ready to Mingle

Whether you’re single and ready to mingle or single-and-happy-alone-thank-you-very-much, Valentine’s Day can be a day to celebrate yourself. If you’re on the hunt for a partner, the best way to attract someone is with confidence so wear whatever makes you the most comfortable and your confidence will radiate—be it your favorite LBD, a perfectly worn-in leather jacket, thigh-high boots…whatever it is, you do you.

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Jacquemus

off-the-shoulder mini dress

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Anthropologie

two-tone hoop heart drop earrings

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Zara

fringed metallic bucket bag

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Paris Texas

leather over-the-knee boots

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Des Phemmes

sequined mini dress

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Floral 3 drop earrings

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Benedetta Bruzziches

Your Best Friend La Grande shoulder bag

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Studio Amelia

Emily leather wrap sandals

The Galentine’s Day

If Valentine’s Day is all about celebrating love then let’s not forget some of the most important loving relationships in our lives: our friends. “Galentine’s” is really just another word for what is, in fact, a girl’s night out—as if we needed any excuse to get dressed to the nines with our friends (be it in pajamas to wear to bed or pajamas to wear out). For these Valentine’s Day outfit ideas, think something with feathers, something with satin, or big bows that you might normally stay away from—this is your night to shine!

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Lake

Lottie shorts set

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Olivia Von Halle

Audrey floral-print eye mask

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Chanel

Le Vernis longwear nail color

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Tata Harper

hydrating hyaluronic acid floral mask

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Sleeper

Black Tie pajamas

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Loeffler Randall

Violet bow-embellished shoulder bag

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Loulou Studio

Sulue slingback pumps

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Westman Atelier

the Spring Edit

Insights, advice, suggestions, feedback and comments from experts

As an expert and enthusiast, I have access to a wide range of information and can provide insights on various topics. While I have personal experiences or emotions, I can offer factual information and answer questions based on available data.

Now, let's discuss the concepts mentioned in this article.

Valentine's Day Outfit Ideas

Valentine's Day is a holiday celebrated on February 14th each year. It is often associated with romantic love and is a time when people express their affection for one another. The article suggests different outfit ideas based on various relationship statuses or date plans. Here are some key points:

  1. The First Valentine's: For the first Valentine's Day in a new relationship, the article suggests a subtle yet festive approach. It recommends wearing excellent-fitting jeans, a top with a pop of red or pink, and some fun accessories and dainty lingerie. This outfit works for different types of dates, whether it's a dinner in a chic restaurant, an at-home meal, or something more casual like bowling.

  2. The Getaway: If you're planning a getaway for Valentine's Day, the article suggests dressing differently from your daily life. For example, if you usually wear jeans and tops, try wearing a charming dress or playsuit for a beach trip. If you're going on a weekend trip or staycation in your own city, opt for a casual but polished combo with a knit and cool corduroy trousers.

  3. The Partner of Many Years: For those in long-term relationships, the article suggests surprising your partner with new lingerie. It recommends a delicate cami set with a sweet lace trim for a subtle but exciting change. Even if you're just spending a cozy evening at home, upgrading your pajamas to a silky pair can add a touch of spice.

  4. The Single and Ready to Mingle: Whether you're single and looking to meet someone or simply enjoying your own company, Valentine's Day can be a day to celebrate yourself. The article suggests wearing whatever makes you feel comfortable and confident. It could be your favorite little black dress, a perfectly worn-in leather jacket, or thigh-high boots. The key is to be true to yourself and radiate confidence.

  5. The Galentine's Day: Galentine's Day is a term used to celebrate the love and friendship between women. The article suggests embracing feathers, satin, or big bows for this occasion. Whether you're having a girls' night out or a cozy pajama party, this is your opportunity to shine.

Please note that the outfit ideas and specific products mentioned in the article are subjective and based on personal preferences. It's important to choose outfits that make you feel comfortable and confident.

Let me know if there's anything else I can help with!

10 Comfortable (and Cute!) Valentine’s Day Outfit Ideas to Copy (2024)

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