Another Valentine’s Day is upon us. This romantic holiday has a complex and fascinating history, replete with beautiful artistry. Valentines went through many transformations to become the ones we know today.

Read on to learn why this year’s Valentine’s Day – which lands on a leap year – has special signficance!

The Origins of Valentine’s Day

Most historians trace the Valentine’s Day as we know it back to Lupercalia, a Roman festival of fertility held in mid-February. In the 5th century, the pagan holiday was replaced with St. Valentine’s Day under the instruction of Pope Gelasius I.

Two saints with the name Valentine share this feast day, so it’s unclear which one Gelasius intended to celebrate with the holiday. More than anything, the renaming of the day was one of many efforts to overwhelm the Roman calendar with alternative Christian holidays. Between the 5th century and the 14th, Valentine’s Day was all but ignored by non-Catholics.

Valentine’s Day in Early Literature

In 1382, Geoffrey Chaucer makes what is believed to be the first connection between this holiday and romantic love in his poem Parlement of Foules. The verse reads: For this was on seynt Volantynys day/ Whan euery foul comyth there to chese his make. Like all holiday history, there is some disagreement about if Chaucer was actually referring to February 14. Either way, by the time the 15th century rolls around, the holiday has become decidedly a celebration of romantic love with grands feasts and parties.

But during these early days, people were encouraged to honor a patron saint as their Valentine instead of a person. From the late 1400s to the mid-1800s, small paper cuts known as devotionals were created as a precursor to valentines. Convents and monasteries produced these beautiful cards, using parchment, vellum or paper, and proceeds from their sale benefitted charity.

The 18th century sees the first true valentines appear, along with the famous valentine poem: The rose is red, the violet’s blue/The honey’s sweet, and so are you. This classic rhyme first appeared in a 1784 book of nursery rhymes. While handmade cards appeared in the late 1700s, very few are still in existence. York Castle Museum has one on display from 1797, which may be the oldest valentine on record.

The First Vintage Valentines

It is in the early 1800s when valentines as we know them – romantic greeting cards – truly gain popularity and we start to see some examples of remarkably artistic cards. Christine Bunish started gathering vintage valentines about 25 years ago and opened her Etsy shop, GatherAntiques, in 2012.

“Valentines are among the prettiest and most fun paper items available, and it’s always wonderful to make a connection with how people celebrated the holiday in the past,” she says.  “When you think about it, it’s a wonder that any paper items have survived past the sender’s and recipient’s lifetime. After all, paper is easy to tear, crease and lose. And items that have been mailed have endured the postal process. So the Valentines we see from 100 or almost 200 years ago are true survivors, sometimes lovingly preserved in a scrapbook.”

Bunish found most of her valentine collection at antiques shows, online and at vintage flea markets. “If you have patience and determination and are not afraid to rummage you can come up with some great finds,” she says.

Esther Howland: The Mother of Vintage Valentines

Valentines that are marked by early makers are highly valuable. One of the best-known early valentine makers is Esther Howland. “She is credited with starting a cottage industry that turned into America’s first commercial Valentine makers,” says Bunish.

In the early 1800s, the Howland family owned the largest stationary and book store in Massachusetts. When Esther received a fancy English valentine from one of her father’s colleagues, she decided to try making her own. They were so beautiful that her brother took several on his next sales trip. Their immense popularity inspired more advanced sales than Esther could create on her own, so she hired help and thus her line of valentines was born.

After a long and illustrious career, Esther sold the business to George Whitney in 1881. Oddly enough, this queen of romance and valentines died in 1904 never having married.

Cobweb Valentines

Bunish adds that, because of their delicacy, some categories of much older valentines are highly valuable. One example is cobweb valentines, produced around 1820. These complex paper projects appeared flat with a printed illustration. But when one lifts a string at the center of the card, the illustration pulls up a cut-paper ‘cobweb’ and reveals a hidden design.

Cobweb valentines are also referred to as flower cages, bird cages or beehives. When you consider the effort these delicate paper artworks required, one must surely have felt the love when receiving a cobweb valentine, particularly a hand-made one. Luckily, because of the nature of the cobweb covering the illustration beneath, many of these valentines are remarkably preserved.

Vintage Victorian Valentines

The Victorian era is known for its prudishness. During a time when courtship was complex and tangled with etiquette, it’s no surprise that love notes became prevalent. Bunish explains that the Victorian age saw the rise of cupids and period costumes on many valentines.

As a collector, Bunish has a particular affinity for the early, hand-colored Victorian valentines. “They look more like sheets of prints than cards,” she says. “I also love the late 19th century valentines with beautiful printing and illustrations, and the hand-made paper lace valentines layered with tissue and die-cut scrap.”

“The artwork on vintage Valentines is often exceptional, and the high-quality printing processes of the 1880s to 1920s produced both subtle and vivid colors,” says Bunish.

Furthermore, antique Valentines were not printed in huge commercial quantities. These were expensive, often hand-made items sold in high-end stationery stores.

Vintage Valentines in the early 1900s

As one might imagine, valentines sent during war-time were some of the most meaningful and sweet. These greetings provide an intimate look into what was often a couple’s only means of communication during a dark time.

This era also saw an increase in the affordability of valentines, which made them more popular. “The early 20th century’s penny postcards increased availability, so pretty and fun Valentine postcards circa 1910 are easier to find,” says Bunish.

Germans made a variety of die-cut valentines in the WWI era, many of them mechanical with moving parts.

Vintage Vinegar Valentines

It’s a mouthful, but one of the most interesting vintage valentine trends was the vinegar valentine. Rather than the sweet and romantic language of typical valentines, these cards sent messages of dislike and disgust. Often cheaply-made, vinegar valentines were relatively common between 1840 and 1940.

Celebrate Leap Year with a Vintage Valentine

Historically, leap years have held a special significance for Valentine’s Day. On these years in which February has an extra day, women were permitted to bunk tradition and propose marriage to men. This year happens to be a leap year, so a leap year valentine would make for a sweet vintage gift.

Whatever your valentine tastes – sweet and sappy or vinegar vicious – estate sales are a good place to hunt for this year’s perfect valentine!

A big thank you to Nancy Rosin, President of the National Valentine Collectors Association, and Christine Bunish of GatherAntiques for providing information and images for this article.