Valentine's Day Outfit Ideas For 2020 | Cute Outfits (2024)

To all my career-driven girls out there, your Valentine’s Day outfit should be both date night-ready and office-appropriate. So, I have here 14, day to night outfits any working girl will love to be caught in on V-day!

RELATED:How To Rock Cute Sweatpants Like A Fashion Girl

Valentine’s Day Outfit Ideas from Work to Date Night

1. Girly Separates


Valentine’s Day is one of my favorite holidays because I really feel the love in the air, even before the day itself! This is why as early as now, I’m planning on a girly Valentine’s Day outfit.

I think I’ll be going for a classic feminine style with my Valentine’s Day outfit this year for a subtle flirty vibe. This coordinating chiffon pleats midi skirt and chic ruffles blousemake for a casual yet date-worthy look!

Keep your accessories simple and neutral. Put on a light makeup but go for red lips and doe-eyed makeup to have your date swooning.

2. Comfy and Bright


Valentine’s day on a weekday is going to be a long and busy day ahead, so dress for comfort! A bright long sleeves shirtand comfy circle midi skirt is a casual yet polished look you can wear from morning till evening.

To get into the occasion, go for shades of red and pink.Since February is still essentially winter, check out the temps in your area.

Make sure the fabric of your outfit will keep you both comfy and warm. You don’t want to take the meaning of “dressed to kill,” literally.

3. Hot Pink Sheath Dress


I love this perfect day-to-night dress, and I’d wear it as my Valentine’s day outfit for work and beyond. A sheath dress is a workwear staple but for Valentine’s Day, go for a loud color and added details.

This hot pink piece with a self-tie waist and a ribbon has a romantic and dressy touch. Pair it with strappy high heels in neutral, and render your guy workmates in awe and the girls, green-eyed.

Turn heads from the time you enter your office to the moment you step into the restaurant for your dinner reservation. Let’s not forget your S.O., with hands to your waist, never wanting to let you go.

4. Pops of Red


One of the easiest ways to go from day to night with your Valentine’s Day outfit is with red accessories! Wear your usual work clothes (or something just a bit dressier), then add pops of red with your choice of bag, shoes, or jewelry.

5. Suit Dresses with a Twist


Got a big meeting on Valentine’s Day? This A-line midi dress with a flare and fit design borders on fun and formal perfect from the boardroom to the ballroom.

You can also put together a trendy three-piece pantsuit. Go for a blue shade pantsuit (which is the color of the year) and a classic white inner shirt.

Take your suit dress from the board meeting to the bar with a statement necklace, bedazzled pumps, and other accessories. Oh, and lose the blazer!

You can amp up your Valentine’s Day outfit with these gorgeous bangles!

6. Peplum


My biggest challenge? Valentine’s Day is on a weekday this year.

That means I’ll be going from work straight to date night, and I need to be ready for whatever surprises my man has in store!

I’m sure a lot of you are thinking the same, too—how do you transition from workwear to evening wear without a complete outfit change? Is it even possible?

Yes, it is with a peplum piece in your ensemble. A peplum top is another girly and romantic silhouette to wear for your Valentine’s Day outfit.

Pick a darker or a more formal color, pair it with semi-formal cigarette pants or dark denim skinny jeans, and you’ve got a day-to-night look. Pointy pump heels should go well with the look.

7. Cozy Layers


Layer up! Or if you’re in the chillier north, bundle up.

A turtleneck is an office staple during these cold months, but give it a romantic touch with a fit and flare dress or a circle skirt combo for a dinner date.

Going for the more casual or IDGAF look with the single ladies on Valentine’s Day? A graphic tee + a denim jacket with matching strappy heels is still a style we’d love to go for even on a holiday, especially with friends.

Simple skinny jeans topped with cozy sweaters and a pair of chunky combat boots will also send a powerful message that you’re not one to mess with… or you’re game for the one who will take a chance!

RELATED:10 Korean Fashion Trends To Steal Right Now

8. Wrap Dress or Belted Blazer Dress


Every working girl needs a DVF wrap dress, and for good reason. You can put on the dress quickly and without fuss—stylish and convenient sums it up.

If the wrap dress is too fun and flirty for your taste, go for a belted blazer dress. It gives you a business-like air in the morning and room to move for the evening Valentine’s Day party.

Wear either dress to the office, to a formal dinner, and even hit the clubs wearing any of these outfits. If you have no idea what’s in store for you on Valentine’s Day, I say go for these!

9. Upgraded Little Black Dress


Of course, any list of occasional outfits isn’t complete without the classic and reliable little black dress. Time and again, the little black dress comes to the rescue.

Besides, it’s Valentine’s Day, you’ve got an excuse to dress up! Upgrade your basic LBD with ruffles, new silhouettes, and of course, bold red lips.

10. Feminine Details


You don’t have to wear skirts or dresses on date night! Pair your regular pants with dressy tops like this black and white blouse with ribbon details.

Give the outfit a formal air with a blazer on top. A pointy slide or black strappy high heels and a pair of hoop earrings will work great with the whole look.

11. Mermaid Skirts


The mermaid skirt is like the upgraded version of your basic pencil skirt, which makes it appropriate for the office and evening events. Pick an interesting top and slip on your most luxurious pair of pumps for a chic Valentine’s Day outfit!

Or, go for a pair of convenient pointy slides, then accessorize with tassel earrings and make a statement with a dressy crossbody purse. It’s the perfect outfit for a stroll with your S.O. after a romantic dinner on the ultimate date night.

12. Midi Dresses


A midi sweater dress with turtle neck is another perfect outfit from day to night on a chilly Valentine’s day. If you’re hanging out with your girls, switch from your office high heels to cozy white sneakers you can dance and get crazy in, all night long.

Like mermaid skirts, midi skirts and dresses also work the same way—they’re long enough to be formal and dressy, but not too long that you’ll look overdressed at work. Keep your accessories nude or basic so it’s even easier to take from day to night!

13. Fun Florals


Why wait until you’re given a bouquet of flowers? We’re strong, independent women—wear it on your dress instead! A floral dress is definitely Valentine’s Day-worthy, and it’s one of the few fun prints you can wear to work, whatever your job is!

Take floral palazzo pants and pair it with a cute light pink long sleeve top, and you’re all set from morning till night. Take a hint from one of our ideas here and accessorize with pops of red.

14. Red Power Dressing


I’d have to say, this and the first outfit ideas are my favorites. This all-red look is so eye-catching, and Valentine’s Day is one of the few times we can actually pull this off in real life!

It’s sexy, fashionable, stylish, and appropriate for the day’s events—all rolled into one. What more can you ask for?

A bright red bodycon dress gives the impression that you’re on top of things from your man to your job. Pick a comfy yet heavy fabric for this cut if you want your baby fats tucked.

Watch this video from Kiki Morabito to get more Valentine’s Day outfit inspiration:

I think you know by now I’m super excited for Valentine’s Day! It’s a tight race between all these great Valentine’s Day outfits I’ve just shown you, but I know I’ll make my mind up before the big day.

Whether you’re with your family, your friends, or with your special someone, you want to look your best from morning till night for your FB and IG posts. You have lots of time as well, so soak up all this inspiration and I’m sure you will look your best!

Do you have any Valentine’s Day outfit inspiration of your own? Share them with me in the comments section below!

Up Next:

  • 14 Fab All Black Outfits You’ll Love
  • Winter Coat Guide | 9 Ideas To Finding The Right One For You
  • Celebrity Outfits For Less | Cute Outfits Guide

Not decided yet on your Valentine’s Day outfit? Get inspiration from these top fashion bloggers!

Follow us on Facebook, Twitter, and Instagram for more Cute Outfit updates!

Valentine's Day Outfit Ideas For 2020 | Cute Outfits (2024)
Top Articles
Latest Posts
Article information

Author: Van Hayes

Last Updated:

Views: 6222

Rating: 4.6 / 5 (66 voted)

Reviews: 89% of readers found this page helpful

Author information

Name: Van Hayes

Birthday: 1994-06-07

Address: 2004 Kling Rapid, New Destiny, MT 64658-2367

Phone: +512425013758

Job: National Farming Director

Hobby: Reading, Polo, Genealogy, amateur radio, Scouting, Stand-up comedy, Cryptography

Introduction: My name is Van Hayes, I am a thankful, friendly, smiling, calm, powerful, fine, enthusiastic person who loves writing and wants to share my knowledge and understanding with you.