what to wear on valentines day heart fashion
blazer: Cinq à Sept, earrings: Lele Sadoughi, bracelet: Argento Vivo, sunglasses: Saint Laurent, necklace: Meira T, lounge set: Honeydew Intimates, sweater: 1901

I am a big fan of Valentine’s Day. Ever since my Mom laid out pretty little love notes and candies at the breakfast table for me and my brothers in the early nineties, I was hooked. Single or committed, I celebrate every year, even if it’s just sending my Mom a cheesy card in the shape of a heart.

Speaking of hearts, I am going to recommend you wear them this year. I have rarely encouraged my clients to wear hearts, but this year’s hearty selection of chic and fun choices are irresistible. Deciding what to wear on Valentine’s Day should be fun, and you are sure to have it in one of these lovely goodies. Plus, they work year-round. After browsing these goodies, check out this post to see one of my personal Valentine’s Day Outfit Ideas.

Honeydew Intimates Sun Lover Lounge Set

heart pajamas to wear on valentines day
Honeydew $54

Because of the pandemic, we’re all spending a lot more time at home and this cozy soft Honeydew Intimates Sun Lover Lounge Set is perfect for lounging around the house. Plus, the black and white heart pattern is fresh for more than just Valentine’s Day.  This heart lounge set is available at Nordstrom, Amazon, Shopbop, and Bloomingdale’s.

Lele Sadoughi Dried Floral Heart Earrings

heart fashion
Lele Sadoughi $150 $90

These Lele Sadoughi Dried Floral Heart Earrings are simply gorgeous. These heart earrings are available at Shopbop, Neiman Marcus, and Saks 5th Avenue.

1901 Intarsia Stripe Crewneck Sweater

heart fashion
1901 $59 $35.40

What to wear on Valentine’s Day depends on what you have planned! But this soft 1901 Intarsia Stripe Crewneck Sweater is a great casual choice for a cozy game night or dinner in.

Baublebar Valentina Resin Heart Stud Earrings

heart earrings
Baublebar $34 $20

You know I love tortoise for its versatility and these Valentina Resin Heart Stud Earrings are a perfect heart-shaped detail for your Valentine’s Day outfit — and beyond.

Cinq a Sept Love Cheyenne Bejeweled Blazer

what to wear on valentines day
Cinq à Sept $695

This Cinq a Sept Love Cheyenne Bejeweled Blazer is so chic and sophisticated. It lets you wear your heart on your sleeve — as well as your shoulder, your back, and your lapel! It’s available at Nordstrom, Neiman Marcus, Bloomingdale’s, Saks 5th Avenue, and Shopbop.

Baublebar Maka Pendant Necklace

what to wear on valentines day heart necklace
Baublebar $48

For another more subtle heart detail to wear on Valentine’s try the Baublebar Maka Pendant Necklace. This heart necklace is available at Baublebar, Nordstrom, Bloomingdale’s, and Neiman Marcus.

Spiritual Gangster Hearts Active Crop Tank

heart fashion to wear on valentines day
Spiritual Gangster $62

You know I’ve fully embraced chic loungewear this year as the pandemic continues. This Spiritual Gangster Hearts Active Crop Tank is cute for working out or for pairing with joggers. This heart top is available at Nordstrom and Amazon.

Maison Irem Earring Heart True Blue

heart fashion
Maison Irem $130

These Maison Irem Earring Heart True Blue are simple, yet sweet.

Hope for Flowers by Tracy Reese Olivia Maxi Dress

what to wear on valentines day
Hope for Flowers $338

Ok, so this Hope for Flowers by Tracy Reese Olivia Maxi Dress doesn’t have hearts. But roses are a gorgeous Valentine’s Day symbol that can also be worn beyond the holiday. Plus, this dress looks fabulous and somewhat warm for those of you planning an outdoor picnic or dinner.

Emerson Road Jaguar Hearts Waffle PJ Set

what to wear on valentine's day
Emerson Road $78

Here’s another option for what to wear on Valentine’s Day for those of you who plan to take advantage of the fact that the holiday falls on a Sunday this year by staying extra long in bed. Plus, these Emerson Road Jaguar Hearts Waffle PJ Set will be great for getting you through the rest of winter.

Baublebar Iris Drop Earrings

heart earrings
Baublebar $44

Make a statement with these Baublebar Iris Drop Earrings. These heart earrings are available at Baublebar, Nordstrom, Bloomingdale’s, and Neiman Marcus.

Meira T 14k Heart Necklace

heart fashion
Meira T $495

The Meira T 14k Heart Necklace is simple and sophisticated. I love the blue sapphire detail on the yellow gold chain.

PQ Swim Wild Heart Sarong

what to wear on Valentine's day
PQ Swim $102

The abstract hearts on the PQ Swim Wild Heart Sarong are subtle. This is perfect for those planning to spend Valentine’s Day somewhere warm.

Comme des Garçons PLAY Polka Dot Tee

what to wear on valentine's day
Comme des Garçons $158

You probably knew Comme des Garçons was going to make the list. I love their PLAY Polka Dot Tee with its cockeyed heart. Pair with a white skirt, white jeans, or a red leather skirt for a rambunctious look this season. This top is available at Nordstrom and Farfetch.

Saint Laurent Lou Lou Heart Sunglasses

what to wear on valentine's day
Saint Laurent $490

Do you have the luxury of spending that Wednesday afternoon in the park with your lover? Try these Saint Laurent Lou Lou Heart Sunglasses. These heart sunglasses are available at Bloomingdale’s, Neiman Marcus, and Net-A-Porter. (For a cheaper, more whimsical option try these red heart sunglasses from Amazon, as featured in my Alt-Summit post.)

Rails Heart Print Shirts

what to wear on valentine's day
Rails $188

Year after year, Rails makes chic and versatile heart tops for both work and play, Valentine’s Day and beyond — they’ve become one of my go-to’s! You can see what heart options they have this year at Nordstrom and Rails.

Sizing Tip: Runs true to size, but narrow in the shoulders.

Argento Vivo Heart Cuff Bracelet

what to wear on valentine's day
Argento Vivo $48

Try this Argento Vivo Heart Cuff Bracelet for a subtle shout-out to all the whimsy of the holiday. Pair with gold hoops or a gold bar necklace. Do not pair with other heart jewelry pieces.

Sizing Tip: It will work on most wrist sizes since you can squeeze it shut and stretch it open.

J.Crew Castlebar Snuggle Heart Skirt

what to wear on valentine's day
J.Crew $110

As you can see in my most recent Vanessa’s Style post, I love this J.Crew Castlebar Snuggle Heart Skirt. It is comfortable, chic, and fun. My only qualm is the bow has a snap that ensures it stays horizontal, but the snap doesn’t stay shut on my skirt. It still looks great without it snapped, but if it really bugs you, have your tailor switch out for a stronger snap, or move the snap over a bit. See my full Vanessa’s Style post for ideas on what to wear with this skirt as well as other yummy heart skirt ideas.

Sizing Tip: Runs true to size. J.Crew no longer runs big.

MICHAEL Michael Kors Pearl Heart Small Leather Clutch

what to wear on valentine's day
MICHAEL Michael Kors $148

Feeling really girly? This MICHAEL Michael Kors Pearl Heart Small Leather Clutch will go great with your rose gold jewelry look. Pair with a super sexy black frock, or embrace the femininity and wear it with something insanely prissy and colorful. Think femme fatal or A Fashion Nerd.

Sizing Tip: It is 6″ wide by a little under 5″ tall with a 2″ depth that widens when you open it. This means you can grab things out of it comfortably and your smartphone will fit in it.

Kate Spade New York Yours Truly – Hallie Canvas Tote

what to wear on valentine's day
Kate Spade New York $198 $99

If you are heading to the park or beach for a picnic, don’t forget this Kate Spade New York Yours Truly – Hallie Canvas Tote. It is large, but narrow, and it has a zipper so you can use it for work or travel. It’s available at Kate Spade and eBay.

Sizing Tip: This bag is 14″ wide, almost 12″ tall, and has a 5 1/2″ depth. For a large tote, this works on most body types.

Rails ‘Taylor’ Flocked Shirt

what to wear on valentine's day
Rails $158

This Rails ‘Taylor’ Flocked Heart Stripe Shirt is one of my favorite items on the What to Wear on Valentine’s Day list. I put this on a client right before her Christmas travels. I love the soft lightweight feel and subtle heart decor. You can sport this year-round, or give that tiny nod to the cupid if you choose to wear this on the 14th.

Sizing Tip: Runs true to size, but narrow in the shoulders.

Alice + Olivia ‘Emmerson’ Burnout Heart Blouse

what to wear on valentine's day
Alice + Olivia $295

Sexy and cheeky, this Alice + Olivia ‘Emmerson’ Burnout Heart Blouse is great for any black skirt or pant looks. It can also pair well with jeans. If wearing just a black bra under a blouse scares you, throw a black tank top under it.

Sizing Tip: Runs small. Order a size up from your usual.

Lucky Brand Heart Matchbox Ruched Back Top

what to wear on valentine's day
Lucky Brand $39.50

What to wear on Valentine’s Day obviously depends on your itinerary. Does your Valentine’s Day involve cooking dinner at home or doing a movie night with girlfriends? This Lucky Brand Heart Matchbox Ruched Back Top is flattering and cozy.

Sizing Tip: Runs large. Order a size down.

Sundry Metallic Heart Side-Zip Sweatshirt

what to wear on valentine's day
Sundry $118

Most of my clients celebrate Valentine’s Day casually, making this Sundry Metallic Heart Side-Zip Sweatshirt the perfect answer to the what to wear on Valentine’s day question. Pair with black jogger pants, blue jeans, white denim, or gold hot pants.

Rails ‘Kelli’ Paris Sweatshirt

what to wear on valentine's day
Rails $148

For the Paris lovers out there, this Rails ‘Kelli’ Paris Sweatshirt might be perfect for your casual Valentine’s Day. Note the “Me and You” written on the heart. Perhaps this is how you tell your friend or partner you got him or her tickets to France?

Sizing Tip: Runs true to size.

Equipment Velvet Heart Sheer Shirt

what to wear on valentine's day
Equipment $298

Equipment’s Velvet Heart Sheer Shirt is another sheer heart option. Again, if you don’t want to wear only a black bra under it, sport a black tank. Do not wear a nude tank as the image suggests; that look is not chic.

Sizing Tip: Runs true to size.

Meri Meri Heart Love Notes

what to wear on valentine's day
Meri Meri $12

I know these have nothing to do with what to wear on Valentine’s Day, but remember those love notes I was talking about? Try these Meri Meri Heart Love Notes for your friends or children. Or start a tradition with your partner, and give them one each year.

Sizing Tip: These look small, but they are quite large; they are 8″ by 8″.