Pillbox Placement Part 2: Last Century

After Monday’s post on how royal pillbox hats have been worn over the past 17 years, I thought it would be interesting to look back further at this famous hat shape to see how it was treated in the past. Here is a look at five decades of royal pillbox wearing in the last century.

1950s: The decade before pillboxes surged in popularity, the few that reached royal heads were low versions, mostly worn high on the head. You can see references (the cutouts on Princess Marina’s hat in the middle, for example) to the calots and other close fitting cocktail hats which were popular at the time.


1960s: The era of the pillbox arrives! The height and scale of these pillboxes noticeably grows, the edges grow rounder and placement moves back on the head. While some royals place their pillboxes close to their hairline, most wear them further back, firmly centred over the crown of the head. The only pillbox tilted at an angle that I’ve been able to find during this era is the one worn by Queen Sirikit during a 1961 visit to London (hat #7 below).
As there have been multiple comments how the pillboxes worn by Jacqueline Kennedy during the early 1960s heavily influence how we remember hats from this era, it feels important to bend our usual ‘royal hats only’ rule for the sake of this discussion. At far left below is the hat worn January 21, 1961 for the inauguration and in the center, is the pale yellow one worn for the infamous 1961 presidential visit to Paris. All of Mrs. Kennedy’s pillboxes are placed well behind her hairline in a very similar way to how royal pillboxes were worn during the same time period above.

1970s: Pillboxes are further inflated, textured and lavishly embellished with ruched scarves, net tulle, woven ribbons, feathers, and a myriad of gigantic bows, trailing ribbons and floral explosions out the back.  Placement is ever so slightly forward from the previous decade- either at the hairline or just behind.


1980s: Pillboxes decrease considerably in size although textured materials and large embellishments remain, often on the side of the hat. Placement moves noticeably forward and the hats are worn snug up to the hairline or up onto the forehead. You’ll notice that many pillboxes during this time are also worn tilted to the side.

1990s: There’s a little bit of everything- bold colour, pattern, texture, veils, bows, feathers. The forward placement and diagonal tilt of the 1980s continues through the early nineties but as the decade progresses, there is a return to the classic placement of the 1960s- straight on the head and off the face with the front rim of the hat a few inches behind the hairline. There is also a return to classic styling- the large bows, blooms and baubles of the previous two decades disappear and hats become more streamlined as the century draws to a close.


 There you have it- more than 70 years of royal pillbox hats!
I’m struck by a few things- first, how similar pillbox placement today is to that in the 1960s (off the face with the front rim placed between the hairline and the top of the head). It’s also interesting that while Jackie Kennedy is widely credited for the popularity of the pillbox, her royal contemporaries were wearing similar hats in a very similar fashion at the very same time (making me wonder who was following who… or if they were all following current fashion of the time?). Finally, Queen Elizabeth’s pillbox placement does not change much over the decades- they all sit fairly far forward on her hairline or forehead (I suspect, a position that works well with her unchanging hairstyle) although she does take part in the 1980s tilt to the side!
I’m curious- what do you notice here? How do you think past trends influence how royals wear pillbox hats today? Do the 1960s designs and how they were worn match the image of the “classic” pillbox you have in your mind? Do you think the 1980s trend of tilting these hats to the side might become popular again sometime in the future?

26 thoughts on “Pillbox Placement Part 2: Last Century

  1. Paola for the absolute outright winner. Masako in the yellow. Farah in green. Michiko in polka dots. None with embellishment on the side or sprouting from the crown – I’m looking particularly at the British abominations.

  2. HatQueen, you are amazing! This is second in scope only to your Queen Elizabeth 90th birthday retrospective. Like many others, I associate the style with Jackie Kennedy and her unadorned hats, so I never expected so much variation in texture, material, and trim.

    I’m never going to like pillboxes as much as brimmed hats, but I have a new appreciation for them. It occurred to me that, positioned correctly, they frame the face in a sort of halo. Generally, the 1960s placement works best. I think the tilted placement is great. We see a lot of that with the current cocktail hats.

  3. Nice to see all of this variety! There are some embellished pillboxes I really like, but too many of them I think are products of their time and should remain there (including their often corresponding outfits).

    Personally I get kinda irked with how often Jackie Kennedy is the one person people refer to when they think of the pillbox hat; as we can see, there were so many royals donning them at the same time, and Audrey Hepburn knew how to wear some fabulous ones as well. If I recall correctly, Jackie Kennedy wore the pillbox because it was the one hat she could stand wearing in a formal setting as she didn’t like wearing hats.

    • Interesting. President Kennedy did not like hats, but I never heard that about Jackie. And, yes, Audrey Hepburn wore them (and really everything else!) beautifully.

  4. So wonderful to have so very many examples grouped and in one place for comparison! I love these compilations. Pts 1 and 2 are both terrific. Thank you HatQueen!

  5. Thank you for this retrospective! I prefer a medium size pillbox that is fairly unadorned except for some small aspect to provide interest. For example, some of my favorites include: 1. From the 60s– Princess Alexandra’s ruched blue pillbox with bow, the one above her with the small side rose, Princess Grace’s blue net covered with small front bow; 2. From the 90s– the Duchess of Kent’s blue ruched with brown edging, Princess Diana’s silver with back bow, and the Japanese princesses’ yellow and blue with small flowers or bows. From this I realize that the style of the hat matters more to me than its placement.

  6. Jackie Kennedy was considered the closest thing to “American royalty” so I am happy to see she was included. Thanks for the fun and interesting retrospective!

  7. I have always disliked the pictures of QEII in a pillbox hat that sat right on her forehead. I felt like she needed to have some hair showing at the front edge of her hat but wondered if it was due to her hairstyle. Having seen some of the pictures above of other royals and the similar placement on them, I have decided it is the placement and I just don’t like it that far forward. I have also found I prefer the simpler, less frou-frou styles. I guess I am more of a tailored kind of girl.

  8. It’s probably inevitable that pillboxes move forward again but I much prefer them worn back like they are today and were in the 1960s.

    I must admit I’m also surprised how many of the royals have that classic pillbox look in the 1960s. I thought that was all Jackie Kennedy but it obviously wasn’t. Queen Paola’s pillboxes are perfect, almost like this style of hat was created just for her.

  9. Is that Empress Michiko in the polka dot 1960s pillbox? If it is, she is ADORABLE. That hat is the cutest pillbox EVER.

  10. What a fabulous retrospective! So cool to see the evolution of placement over time. It’s also interesting to me to see the amount of variability in what I previously thought of as a fairly calm and narrow category of hats.

    Most of these are lovely, but I think my favorites from this group are:

    1. QEII in the 1980s polka dots. JUST WOW, I love this, and it seemed so timely and yet so cute. I feel like in a slightly smaller scale of hat and a more contemporary colorway, the York princesses could pull of these vibrant polka dots today.

    2. Princess Diana in the 1990s pink straw. Lovely scale, shape, and placement.

    3. Queen Beatrix in the 1980s black with the bow- so fun, and again a nice size and shape. Cute with her pink coat!

    4. Princess Grace on the bottom/last in the 1960s panel, navy blue with a tiny bow and what looks like very snug netting. Love the slightly more tipped back and slightly larger scale of this one. In some ways the look (if not the hat itself) reminds me of the beautiful retro look worn by Viscountess Linley to the service of thanksgiving for QEII’s 90th birthday.

    The most surprising thing to me, is that in spite of my love for the classic look, by far my favorite group of these is the ones from the 1980s! I’m usually not much of a fan of the dresses of that era, but overall, it’s definitely my favorite group of these hats.

  11. What a lot of fun! You’ve done some serious research here! A lot of these I wouldn’t have thought of as pillboxes actually, but I get the basic shape makes them so. For me, the real mistresses of the style are Paolo (so beautiful as a young woman), Grace and Alexandra.

    I guess what this tells us is how timeless this style is, because every age has reworked it.

    I went to a wedding with a friend about 10 years ago, and we went to Selfridges and bought her a fuchsia pink Phillip Treacy pillbox. Now I’m quite tall but she’s quite short…. Before the wedding I positioned it forward tilted over one eye. From my angle it was perfect – the photos told another story. She was swallowed by the bloody thing. Fortunately before the day was out she realised and pushed it to Jackie O style!!

    • I pushed the definition of pillbox here to try and show how different eras have experimented with the shape (along with positioning). As you said very well, every age seems to have reworked it.

      Your story about placing your friend’s pillbox is charming! I admired a similar Philip Treacy bright pink pillbox at Selfridges 12 years ago. My travelling partner told the sales clerk I had crossed a continent and an ocean to see a Treacy hat in person (a slight stretch of the truth) and the sales clerk insisted I try one on before we left. Eyeing up my cargo pants, Tshirt, ponytail and walking shoes, she said that the pillbox wasn’t the right hat for my ensemble and brought me a butterfly printed trilby embellished with silk monarch butterflies in every colour under the rainbow. Looking back, I’m thrilled to have had that iconic hat on my head (a collection made for McQueen I think) for a few minutes but at the time, I was really disappointed not to try the pillbox.

  12. Who is the beauty in the lime green hat and jacket/coat, daisy earrings and sunglasses, 4th row down in the 1960’s collection? So many beautiful hats in every decade. I don’t have a favorite for placement. I think it depends on the face, the hairdo, the overall shape of the hat.

  13. It’s so interesting to see how the pillboxes crept forward during the 70s and 80s and now have moved back again. The 1980s ones tilted to the side are so cute and I’ cant believe even Queen Elizabeth tilted hers!

  14. Gorgeous! I wouldn’t mind at least two dozen of those hats. I prefer the ones from the 60’s the most. I always associate them with that era. Jackie Kennedy, Queen Anne Marie, and Queen Paola looked amazing I thought, but most of the royal ladies looked good in that style. I tihought they didn’t look as good on Diana. They were too small and didn’t sit right on her hair. I much preferred her in bigger, dramatic hats or smaller hats that weren’t pillboxes. She could really rock a hat.

    • Ditto here – the 60’s were my fav for the pillbox hat – even Bob Dylan wrote a song referencing pillbox hats with his ’66 Leopard-Skin Pill-Box Hat

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