What to Wear on Valentine’s Day – Heart Fashion

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 us kids back in the mid-1980s, 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 never encouraged my clients to wear hearts before this moment, 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.

Rails ‘Taylor’ Flocked Heart Stripe Shirt

what to wear on valentine's day

Rails $158

This Rails ‘Taylor’ Flocked Heart Stripe Shirt is my favorite item 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. The shirt is available at Bloomingdale’s, Neiman Marcus, and Nordstrom.

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

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.

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

Alice + Olivia ‘Emmerson’ Burnout Heart Blouse

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. This shirt is available at Nordstrom, Saks Fifth Avenue, and Neiman Marcus.

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 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. This shirt is available at Nordstrom, Dillard’s, and Macy’s.

Sizing Tip: Runs large. Order a size down.

MICHAEL Michael Kors Pearl Heart Small Leather Clutch

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.

Comme des Garçons PLAY Polka Dot Tee

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.

Saint Laurent SL196 Lou Lou Mirrored Heart Sunglasses

Do you have the luxury of spending that Wednesday afternoon in the park with your lover? Try these Saint Laurent SL196 Lou Lou Mirrored Heart Sunglasses.

Sizing Tip: At 55mm, these are best for wider faces.

Kate Spade New York Yours Truly – Hallie Canvas Tote

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.

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 Ingrid Heart Print Chambray Shirt

what to wear on valentine's day

Rails $158

This Rails Ingrid Heart Print Chambray Shirt can be paired with jeans, and skirts from denim and tweed to leather and ponte. Find the pairing that works best for your occasion.

Sizing Tip: Rails runs true to size, but is generally more narrow. If you have wider shoulders, skip this one.

Argento Vivo Heart Cuff Bracelet

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.

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. This sweatshirt is available at Bloomingdale’s and Saks Fifth Avenue.

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? This sweatshirt is available at Nordstrom, Bloomingdale’s, and Saks Fifth Avenue.

Sizing Tip: Runs true to size.

Equipment Velvet Heart Sheer Shirt

Equipment’s Velvet Heart Sheer Shirt is another sheer heart option. Again, if you don’t want to wear only black bra under it, sport a black tank. Do not wear a nude tank as the image suggests; that look is not chic. This shirt is available at Bloomingdale’s, Neiman Marcus, and Saks Fifth Avenue.

Sizing Tip: Runs true to size.

Rails Kate Heart Print Silk Shirt

what to wear on valentine's day

Rails $188

This Rails Kate Heart Print Silk Shirt is the most versatile answer to the what to wear on Valentine’s Day question because it is great for work or play. The pairing options are endless—from a conservative pencil skirt to a frilly chiffon poufy skirt—you can wear this with just about anything, including leggings.

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

Meri Meri Heart Love Notes

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″.

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