Royal Halloween: Anne Boleyn

This second part of my series on Halloween costumes inspired by royal ladies is dedicated to one of my all-time favorites: Anne Boleyn. I think she is a fascinating woman and I have read much about her so this blog post will include some ideas for how to dress like her for Halloween in addition to some books I recommend you read if you are interested in her. Some people see her as a tragic figure, a woman who spent seven years waiting to marry Henry VIII only to be executed a few years later when she failed to bear a son. While I believe wholeheartedly that Anne was innocent of all of the accusations of adultery, incest, and witchcraft that were thrown at her by people who called her the ‘great whore’ just before she was beheaded I don’t see her as a saint, either. Katherine of Aragon was so badly mistreated by Henry VIII and Anne that I tend to take her side in this royal, scandalous love triangle that still captivates people to this very day. But I also acknowledge that Anne was intelligent, educated, opinionated, and outspoken. These are traits that her daughter, Elizabeth I, would inherit. So in a way there never would have been a Golden Age of English history if Anne and Henry had not married and had Elizabeth together. Can you imagine?

Hever Castle portrait

Portrait of a Young Anne, Courtesy of Hever Castle

Fashion wise, Anne was often criticized by the public for dressing in too many French designs. Yet her contemporaries always commented that she was never seen with a hair out of place and that she would frequently change clothes multiple times a day in order to maintain her image as queen. In the many books I have read about Anne Boleyn it is clear that many people did not see her as a great beauty. Some called her homely while others described her as plain her worse. So Henry VIII lusted after Anne not because of her physical beauty, but because of her intellectual powers in conversation. Combine her intelligence with the fact that she was most likely the only woman in England who would dare deny the King her bed and Henry was besotted by her. She would not settle for being anything less than a wife. And we all know how that turned out. Helen of Troy may be the face that launched a thousand ships, but Anne Boleyn is the woman who provoked the Protestant Reformation.

Anne’s Beauty

“She was unrivalled in the gracefulness of her attire, and the fertility of her invention in devising new patterns, which were imitated by all the court belles, by whom she was regarded as the glass of fashion” Nicolas Sander- “The Rise and Growth of Anglican Schism”

By contemporary accounts, Anne Boleyn was not typically described as a great beauty. This may be due to people’s personal prejudices against her in addition to the fact that her teeth were not perfectly straight and she was rumored to have six fingers on her right hand, a supposed sign that she was a witch. However, other accounts claimed she merely had an extended or unusual finger nail on one hand with some moles on her skin. This may seem trivial to us but the Tudors believed that you could read a person’s character based on their birthmarks. By most accounts she had long black hair, which she was very proud of because it was shiny and thick, olive skin that sometimes appeared “sallow” or jaundiced especially later in life and dark brown eyes that appeared almost black. In Henry VIII’s correspondence with Anne he describes being struck by the intensity of her dark eyes the moment he first saw her. It is difficult for us to know now, 500 years after the fact, if Anne was really ‘beautiful’ or not since beauty is subjective and standards change throughout time. I believe that Anne was most likely attractive but not necessarily a great beauty and when people described her as “homely” or “plain” or even “ugly” they most likely did so because she had olive skin and dark hair and eyes which were not fashionable at the time. Tudor standards dictated that women should have very fair, porcelain skin and light hair and eyes to give them an angelic or virginal look since ladies with fair hair and light eyes were seen as more submissive. Anne stood out with her dark features which made her look more exotic. I have discovered a compelling waxwork of Anne from Hever Castle. They used various portraits and contemporary descriptions of Anne to create this wax figure. It was NOT created directly from her skull since her remains have not been exhumed because Her Majesty Queen Elizabeth II thinks it is disrespectful. Nevertheless, I think this gives us an idea of what Anne might have looked like in real life.

Anne Boleyn WaxworkAnne+Boleyn+waxwork+2

So if you are planning on dressing up as Anne for Halloween an important element of your costume would be a black wig (if you don’t have dark hair already), since her hair was very dark and was one of her trademarks (pictures are links).

But keep in mind that when in public Anne would not wear all of her hair down as is so commonly depicted in movies and TV shows. Her hair would be up, so I suggest just pinning your hair/wig into a bun.

When it comes to makeup you should wear very minimal to look very natural. I would recommend using rosebud salve as a lip balm. I love this salve and first found it in a Victorian Trading Co. magazine for much more than what I found it for here. You can use it on your lips and it gives them a natural pink but you can also put it on your cheeks and on your brow bone (not ON your eye lid but above it underneath your eyebrow). It gives you a natural flushed look.

The Rosebud Perfume Co has only been around since the Victorian era but I think using this product is appropriate when trying to achieve a Tudor look because rose oil or extract was commonly used for cosmetic purposes during Anne’s time.

Anne’s Jewelry

Anne Boleyn Portrait

If there is one singular element of Anne Boleyn’s style that is emblematic of who she was it is her iconic pearl necklace with a “B” for Boleyn pendant and three drop pearls. You simply cannot dress as Anne Boleyn for Halloween without this necklace because it is the one part of your costume that will identify you as Anne as soon as people see you. I found this great replica necklace that is really pretty and a good quality for $24. I really love it.

But as you can see from the portrait of Anne she would also wear many long strands of pearls in addition to her pendant necklace. Jewelry was very important to the Tudors as it was a sign of their wealth and status. So in addition to the pendant necklace I would buy something like this 60 inch strand of simulated pearls and wrap them around your neck once. They used to be $48 but are on sale right now for $8. The great thing about these is that they can be used for different outfits or costumes as well. Like a flapper costume from the 1920s or maybe a Downton Abbey inspired costume.


Tudor jewelry can look pretty heavy by today’s standards. For example, these large ruby earrings that actress Natalie Dormer wore in the TV series the Tudors when she played Anne. So if you would like to buy some other accessories to go with your Anne Boleyn costume you may want to try something like these earrings below which are reminiscent of something that was worn during the Tudor era but they are still modern enough that you can wear them all Fall/Winter long. They are not specifically meant for a costume so if you are like me and like to buy something that can be worn multiple times, not just for Halloween night, these earrings would work well. They have the ornate gold filigree that was popular during the Tudor era along with the pretty dark red stones that look like rubies, which is appropriate since rubies were very popular at Hampton Court. Yet they are still delicate enough to work with daily wear, not just as a costume. These earrings are made by 1928 Jewelry, a company that specializes in making jewelry inspired by vintage pieces.


Or, if you wanted to continue the pearl theme to match with the “B” necklace, these earrings also by 1928 jewelry could work as well.

Natalie Dormer red earrings

Here is another picture of Dormer from the Tudors. Even though this TV series was definitely not the most historically accurate production I think it can serve as good inspiration when trying to put your costume together.

I like these red earrings for $27. They could probably work for a Victorian costume, too.


The Tudors, also loved their brooches and Anne is no exception. Normally they would place it on their bodice in addition to large strands of pearls like what you see in the picture from “Anne of a Thousand Days” above. I actually like the costume design for Anne from this film more than the Tudors TV series. When putting together your Anne costume the more pearls and gems the better, really, because the more jewelry a person wore during the Tudor era the more important they were or the higher their social status. This goes for both women AND men which is why Henry VIII was adorned with large brooches and his clothes were embroidered with real pearls. This pin from 1928 Jewelry is $22 and reminds me of the brooches that the Tudors would wear but I would personally wear it to pin a scarf or to pin onto my coat or jacket during the winter. Again, this is something that can be worn after Halloween since brooches are very regal looking up to this very day. Most royal women continue to wear brooches including the Duchess of Cambridge, Queen Elizabeth, and royals from many other European royal families.

Anne’s Wardrobe

A completely historically accurate Anne Boleyn costume is hard to come by and can be VERY expensive. But I have found a few pieces that I really like. (Although I may not be completely accurate in all of the pieces I choose in this post, I choose them because I think that they are more affordable and/or so that they can be worn more than just for Halloween).

Just like Anne’s iconic “B” necklace, another vital component of an Anne Boleyn costume is a French hood. This hood in addition to the “B” pearl necklace is what makes Anne’s look stand out, and it is what will make you recognizable as Anne Boleyn and not just as a Tudor woman in general or someone from that period of time. Without the “B” necklace and the French hood you could be anyone from Hampton court. The reason why the French hood has become so synonymous with Anne’s style is because of the time that Anne spent living in France. The years she spent there acted as a finishing school of sorts so that when she came back to England she could not only speak French fluently, but she could also flirt and banter in conversation with men and women alike on a variety of topics including politics and religion which were considered taboo for a woman to speak about in a time when women were expected to be largely submissive to men. While many of Anne’s contemporaries called her ‘homely’ or even ‘the great whore’ no one really ever called her dim or stupid. And I think that is largely why Henry because so obsessed with her.

Anne Boleyn hood

By the time that she became queen one of the most common complaints about Anne is that she did not dress like an English queen. People said that she dressed too French, including her beloved French hood. This was seen as greatly disrespectful to English people because of the long historic turmoil between England and France. So wearing a French hood is an absolute must if you are going to dress as Anne. This French Tudor hood head piece is $49. It comes in a few colors but I think black is probably the one most closely associated with Anne.

When it comes to the dress itself, Tudor costumes can be really expensive. This one was the most reasonable one that I found with a neckline that was most like what Anne is depicted wearing in her portraits. And if you did get this costume the red earrings would look really nice with it.

You could also get the French hood in Gold which would match the costume nicely.

Book Recommendations

I am an avid reader and have my degrees in history and English literature so I have read many great books on the Tudors. Alison Weir is one of the very best and most respected Tudor historians and her work “The Six Wives of Henry VIII” is fantastic. It is not a quick read, but I find it to be easy to follow and insightful.

If you would like to learn about Anne’s sister who was a mistress to Henry VIII before he set his sights on Anne I recommend Weir’s work “Mary Boleyn: The Mistress of Kings.”

And another work by Weir called “The Lady in the Tower: The Fall of Anne Boleyn” is also a must have for anyone interested in Tudor history. This work specifically focuses on Anne’s last days before her execution. I am amazed at how articulate and eloquent she was when she gave her final speech before being beheaded. I can’t imagine how she was able to speak so clearly when she knew she was about to be killed.

If you would like a comprehensive biography of Anne’s entire life I would recommend Eric Ives’ “The Life and Death of Anne Boleyn”.

I hope that you are enjoying reading these posts and getting inspired to plan your own Halloween costume! Stay tuned for the next installment!


The Frugal Lady

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