Inside: Sweet Valentine’s Day outfit ideas winter weather vibes. It’s cold, but it’s time to warm up with your Valentine.

Valentine’s Day is just around the corner, and whether you have plans for the girls or plans with your man, we need to plan a super cute outfit for whatever the evening holds.

If you love the colors pink and red, this is your time to shine, you can always break out your favorite pink sweater in combination with those red trousers you’ve got hidden in your closet for a special day.

Or, maybe you’re not that into color in general, and all black is always going to be the classiest look out there. Whichever way you lean, here are 37 sweet Valentine’s Day outfits winter weather. Sometimes it’s hard to dress cute and sexy for such a fun holiday when it’s so cold outside, but we’re gonna talk about how to keep the vibes alive even in that chilly winter weather.

Check these out!

valentine's day outfit ideas winter

Wherever you are, whatever you’re doing, and whatever you want to channel this evening, I’ve got an outfit for you! Heading to dinner with your fave? Doing something cool and casual and different like going to a museum? You’re going to find exactly what you need here.

What Do You Wear On Valentine’s Day When It’s Cold?

Generally, every Valentine’s Day is a pretty cold affair. Being in the middle of February, one of the coldest months, you always have to get a little creative with your layering and with your original outfit to make it appropriate for the weather but still a fun and cute outfit for whatever the holiday cold.

I’m always a fan of a fun pink sweater, something bold to catch the eye. If you need more of a black sweater and pink pants situation… I think that’s pretty fire too. It’s fun to take Valentine’s Day to a new classy level, so even if your style is usually pretty casual, throwing on a nice peacoat will make the occasion a little bit more dressy and special for whatever your plans are for the day. Even daytime outfits are cute to dress up a little bit, and I think going into night, it can transition well, unless you plan to change between outings.

If you don’t want to be outdoors, you can be a little bit relaxed with all of the layers and all the precautions you have to take with staying warm during the season. But if you plan to take a little stroll around the cute shopping center while sipping some hot chocolate before dinner reservations, or anything else outdoors for that matter, you’re going to want to prepare.

So think sweaters, lace base layers, and a nice overcoat to make your outfits work.

Valentine’s Staples Pieces

If you’re not sure where to start, there are a few Valentine’s Day outfit staple pieces that you need to have in your wardrobe, if you don’t already.

A black slip midi dress will never disappoint, and layering it with the lace long sleeve makes it perfect for the winter vibes. Anything velvet, like a velvet babydoll dress would be so cute. Anything pink or red, your favorite pink blouse, a red blouse, a red, mini dress, a pair of hot pink trousers… No matter how bold or how mild you are with your color add ins in your wardrobe, anything pink or red is a classic.

It feels a little cliche, but it’s only because it’s so fun and it’s the one time that it feels acceptable to wear hot pink if you want to, if you don’t usually. If you already are a pretty colorful person, I’m sure now is your favorite time to break out those colorful, hot pink and red pieces that always feel a little bit bold. Now is their time to shine and yours!

Color, sexy, and sleek. These are all the makings for a great Valentines Day outfit for you and your boo’s special date.

Let’s Wear Pink For Winter 2023

What’s on trend in winter 2023? These are good questions to ask when picking your Valentine‘s outfits, so not only do you want to cater to Valentine’s vibes, but the correct winter vibes for this year.

Some really trending pieces right now are preppy and tailored looks. But in a very elegant and old money way, not the random business casual vibes we had going in 2015. Think Gossip Girl winter in New York, and that’s the move. It’s timeless, and will be elegant for any form of date night.


Knee high boots or over the knee boots are killer in the winter, and it keeps your short shorts and mini skirts in use. Though out of season, it’s kind of an edgy look in my opinion to just randomly break out the leather shorts mid winter… and with a pair of leather over the knee boots?! Incredible. And great with a hot pink sweater for Valentine’s Day.

Dopamine dressing is still in full swing, so get your colors out and get ready to rock some fun pieces. Dressing colorfully and excitingly are the best ways to bring some fun to the dull winter seasons that I know you’re going to love. Just have fun with it! That’s literally all that matters.

Cozy and oversized jackets and vests are hot right now, so you can stay warm and comfortable while rocking these pieces. Don’t stress your outer layers, the cozier they are, the more stylish.

Classy outfits in red and pink


Classy is never a bad idea on Valentine’s Day. It’s a special day, so dress accordingly! Even if you’re not going all out at the bougiest restaurant on the block. Here are some stunning and classy winter Valentine’s Day outfit ideas.

1. Mixed Whites
2. Red Suit
3. Sweater And Leather Shorts
4. Red And Pink
5. Black Blouse
6. Sparkly Top
7. Tiered Babydoll Dress
8. Corset Top

Specific aesthetic styled Valentine's Day outfits

Aesthetic Valentine’s Day Outfits

Have a certain aesthetic you want to keep on the day you celebrate with your sweetheart? Here are some valentine’s day outfit ideas for winter to keep both vibes alive.

9. Color Crush
10. Tulle Skirt
11. Decked Out
12. Trendy Girl
13. Fun Pairings
14. Vintage Vibes
15. Berets
16. Pink Floral Dress
17. Street Layers

Casual outfit, girl in blue jeans and red sweater

Casual Winter

Winter is the time to get all cozy and casual. Casual is still cute, so here’s some inspiration to hit both.
18. Top And Jeans
19. Cardigan
20. Pink Trousers
21. Pleated Skirt
22. Hearts Sweater
23. Festive Cardigan
24. Red Pops
25. Red Mini And Sneakers
26. Colors
27. Pink Shacket

Dresses for Valentine's Day In Winter


Dresses are a perfect go-to. Try these out.

28. Red Velvet
29. Super Sparkly Wrap Dress
30. Green Bell Sleeve
31. V Neck Retro Dress
32. White Sweater Dress
33. Ribbed Dress
34. Red Mini
35. Knit Bell Sleeves
36. Black Sequins
37. Button Front

Valentine’s Day isn’t fun every year for everybody, but it does get fun when you get to celebrate the holiday with someone you really care about and love!

Even more fun when you celebrate and style getting to dress up and sit in a sexy outfit for your partner, and just enjoy being together and celebrate your love! Whoever your valentine is this year, they’re gonna love whatever you choose to wear, and they’re going to love celebrating the holiday with you!

Spoil them, and get ready to get spoiled in return, and enjoy this day centered around love and celebration.
Planning to wear some bold red outfits? Here are 33 ideas for you. Red is such a fun color that people tend to shy away from, but if you can channel the courage to break it out, have at it and be ready to turn heads.

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