Pillbox Placement Part 1: 21st Century

There was an interesting discussion in the comments last week about the ‘correct’ placement of a pillbox hat (brimless hat with a flat top and straight sides that resembles a round cake tin). This threw me into the photo archives over the weekend to do some research. While ‘correct’ is subjective, there appear to be five distinct royal positions for a pillbox hat as we have seen this design worn so far this century:
Position 1: “Over The Forehead” The least common position, unless you’re Princess Beatrix or the pillbox has a cocktail hat vibe.


Position 2: “At The Hairline” Here, the front rim of the hat follows just behind the wearer’s hairline, leaving a sliver of visible hair. Princess Kiko and other Imperial royals seem to favour this position. If the pillbox is tall, this placement works well (keeping the piece away from the back of the neck).

Position 3: “Just Back” One of the two most common placements for pillboxes these days, this position leaves an inch or two of hair in front of the hat to frame the face. The centre of the hat generally sits over the crown of the head.


Position 4: “Off The Top” Perhaps the most common pillbox placement today, the front rim of the hat sits near the middle of the top of the head, leaving several inches of visible hair in front. The back rim of the hat roughly follows the occiptal bone around the back of the head – the center of the hat falls just below the crown of the wearer’s head.

  Embed from Getty Images           

Position 5: “Off The Back” The front hat rim is placed near the crown of the head leaving the hat to sit nearly (or completely!) vertical down the back of the head. Unless the hat is very large, the hair on the top of the wearer’s head will remain mostly uncovered.

This exercise left me with a few questions. Have royal pillbox hats always been worn primarily off the face? Has royal pillbox placement changed much since the 1980s? The 1960s? Stay tuned tomorrow when we break down pillbox placement during the last century (1950s through 1990s) and look for ways past fashion might influence how this classic hat shape is worn today.

For now, I’m curious about which one of these pillbox placements you think works best. What factors influence this? Does one position work better with shorter or longer hair? Does face shape matter? What about size of the pillbox?

23 thoughts on “Pillbox Placement Part 1: 21st Century

  1. Such good observations, by HatQueen and the commenters! My two cents: position #1 tends to overwhelm the wearer, and position #5 just looks awkward. I’m interested to see that, based on these photos, some royals, like Princesses Beatrix and Kinko and the Duchess of Cambridge, have a preferred pillbox position. Others, like the Countess of Wessex and Queen Maxima, vary rhe positioning depending on the hat and hair.

  2. A pillbox was meant to be worn off the face and towards the back. The severity of the shape needs the softness of hair for a better effect. Those on the forehead make for a harsh effect of the facial features. Noses become bigger, foreheads become broader or longer. If the hair is to be worn up at the back it still needs softness of hair around the face.

  3. I wonder how the pillbox stays secure especially with #5. Is there a comb or pins? I’m always afraid that the taller ones will fall off!

  4. Thank you for posting this.
    While not royalty I’d like to see Jackie Kennedy included in this collection of pill boxes hat wearers.
    It was her hat wearing which made me love pillboxes.
    And as I wear glasses it is one of the few styles that actually looks good on my head.
    I don’t think I’ve ever seen Queen Elizabeth in a hat while wearing glasses ( I could be wrong ).

  5. Thank you for an excellent post. It helped me jell why I felt certain ways about some of these hats!

    And brought forth a question: I noticed Queen M in the first group and liked her hat but it brought to mind an issue that I haven’t seen discussed here but would appreciate some thoughts. How does one match hats and placement with eyeglasses? Please don’t just say get contacts….not an option for some. But it is often a juggling act and does present balance of appearance issues

  6. Suddenly Princess Beatrix’s hat styles make sense to me! I think 3 and 4 work the best. 5 seems like it is falling off or a cover for an updo. The small hat of Princess Charlene’s on the back of her head doesn’t even make sense. It’s almost like someone tacked it on when she wasn’t looking.

  7. 4 is what I would consider “classic” pillbox placement, it’ll be interesting to see if that’s borne out by the look at previous decades. A number of these, although they fit a basic definition, don’t say “pillbox” to me – too large (Beatrix, I’m looking at you), too short / flat, not straight-sided enough (Serena, Laurentian). However, I do agree with others that it’s the individual hat and the individual wearer that determine what angle looks good, and it’s extremely difficult to make any sweeping statement. Perhaps like many people, I’m always judging pillbox-wearing against a mental image of Jackie Kennedy, because pictures of her are the first time I was aware of this style of hat.

    Thanks, HatQueen for this splendid review – it must have taken a lot of work!

    • You’re welcome! Last week’s discussion got me curious.

      And you’re right- some of these pillboxes are more rounded than others and I couldn’t resist throwing in the Duchess of Cambridge’s recent square one. There are always variations within each hat type and this probably impacts placement on the head as well.

  8. What a wonderful post! Thank you! I notice that with the exception of the Countess of Wessex and Princess Beatrix (whom it appears to suit the best), all the wearers of the position 1 are Scandinavian. Curious. As with most of the other commenters, I prefer positions 3 and 4. Wearing a pillbox in position 5 almost makes it a different sort of hat, in my opinion.

  9. I am going to show my husband this article. For years he has been urging me to wear hats very far forward, sometimes to the point of obstructing my vision! Hopefully now he can see that anything goes. I will cite Hat Queen as The Authority in the future and save some heated arguments, I hope.

  10. Generally speaking, I prefer 3 and 4, but this roundup illustrates for me that a lot depends on the specific hat and wearer. Hat size, shape, embellishments all play a part. The wearer’s face shape, hairstyle (shorter or restrained, please!), and the rest of the ensemble are also factors. Interesting to me that the same wearers are in multiple placement categories, each time looking fabulous (Esp. Sophie, Max, CP Mary and Kate Cambridge. Paola, Anne Marie, and Birgitte Gloucester also wear pillboxes especially well – guess I particularly like them with short hair.)

  11. My favorite position for a pillbox is at the hairline, because the hat looks completely secure, without being jammed down over the forehead. Just back and off the top can be good as well, depending on the hat and the hairstyle. I think smooth, pulled back hair looks best with a pillbox. What an interesting post to study!

  12. I’ve never stared at pillbox hats so closely! What a fun and informative post.

    First of all, I’m surprised how good so many different people (hairstyles, face shape, age) look great in a pillbox. I wouldn’t have thought they would be flattering on round faces but they are. Surprise! I think oval faces look better with the hat further forward. I’m looking at Sophie Wessex here- the navy hat worn off the back of her head makes her face look even longer but the leopard print one frames her face much better.

    I’m usually on Team Hair UP but looking at Maxima, Mary and Kate here and I really like how their hair half up half down works with the hat. It doesn’t look like a marshmallow stuck on their head like some pillboxes do. The hair down really works.

  13. I’m definitely in favor of 3/4– they feel the most balanced. I’m uniformly against 5, every time I see a pillbox back that far it feels like it’s going to fall off. I don’t care for 2 either- it’s kind of wishy-washy. 1 works, but only IMO with larger hats, and only with down hair, not long down hair either, but shorter down hair that has some fullness around the face. E.g. QSonja, QBeatrix, and PAstrid look fabulous with forward placement, but IMO it doesn’t work on the others in this montage.

    So excited to see the next posts about pillboxes through history.

    And, although all these ladies look well turned out, I really prefer pillboxes that have a little bit of height. The really flat ones, (e.g. Martha Louise, the C of Wessex and Charlene) look to me like they aren’t sure whether they’re percher hats or pillboxes.

    • Also, though there are a bunch of really outstanding hats here, if I had to only pick one it would be PLaurentien in brown with the feather and the purple collar. I have no recollection of the rest of that outfit, but the part we see here (hat plus collar) is fabulous!

  14. Just back is my favorite placement, and I think any hairstyle that is neat and elegant works well. I am not a fan of long hair worn down with this kind of hat, bcauue it can so easily look messy.

  15. I’ve died and gone to pillbox heaven!

    I like positions #3 and #4 best off the face with a bit of fringe. Not keen on Princess Mabel’s slicked back look but love the half hair down on Kate, Mary and Maxima. That’s brilliant. Wish Victoria would try that.

    Thanks for this. Some hats here I had forgotton and it was so lovely to see them again. The best remedy to an absolutely crap day.

    • Forgot to say that I don’t usually like pillboxes over the forehead but Sophie and Princess Astrid’s at those saucy angles are fab!

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