The pillbox hat: history, the Jackie Kennedy moment and how to wear one
A pillbox hat is a small round brimless hat with straight upright sides and a flat top, named after the little cases that once held pills. It sits neatly on the crown or towards the front of the head and reads as one of the most refined shapes in millinery. Jacqueline Kennedy made it a global icon in the early 1960s, and it remains an elegant choice for weddings, Royal Ascot and any occasion that asks for polish.
What is a pillbox hat?
The pillbox is defined by its geometry. There is no brim and no crown in the traditional sense, only a shallow cylinder of firm sides and a flat top that echoes the pill cases of the eighteenth century. That simplicity is the whole point. With nothing to hide behind, the shape lives or dies on its proportions, the quality of the block and the finish of the fabric, which is why a properly made pillbox looks so composed.
Ours are hand blocked in London over wooden forms, one of one, in felt, velvet, silk and straw depending on the season. Because the shape is architectural, it holds colour beautifully, and we can match any shade from a photograph or a fabric swatch so the hat sits perfectly with your outfit.
A short history of the pillbox
From Roman caps to the parade ground
The pillbox began as military headgear. Roman soldiers of the late empire wore the pileus pannonicus, a stiff cylindrical cap that is the clear ancestor of the shape. Centuries later the design reappeared on the parade grounds of the nineteenth century, worn as a forage cap by regiments of the British Army and across the Commonwealth, usually held in place with a chin strap. You can still see the ceremonial version today.
The pillbox becomes couture
The women's pillbox arrived in the 1930s, when couturiers took the disciplined little cap and turned it into an emblem of modern elegance. Milliners worked it in wool, velvet, organza and fur, sometimes softened with a veil, always relying on clean lines rather than decoration. By the 1950s it was established, and then one wearer made it unforgettable.
The Jackie Kennedy moment
On 20 January 1961 Jacqueline Kennedy arrived at her husband's presidential inauguration in a fawn coat and a simple beige pillbox designed by a young American milliner named Roy Halston Frowick, known professionally as Halston. Among a crowd of women in heavy fur caps she looked clean and modern, and photographers could see her face. The image travelled around the world within days.
There is a lovely accident in the story. The hat was made a little small, and to keep it from lifting in the wind Mrs Kennedy pressed a hand to the side, leaving a soft dent in the crown. Women copied the dent, believing it was the design. That single appearance launched Halston's career and turned the pillbox into the defining hat of the decade, worn high on the back of the head with a bouffant beneath it.
How to wear a pillbox hat today
A modern pillbox is more versatile than its formal reputation suggests. It suits sleek tailoring and it lifts a soft occasion dress, and because it frames the face without shading it, it photographs wonderfully. The singer Frank Sinatra put the art of wearing a hat into five words.
Cock your hat, angles are attitudes.
Where to position it
There are two classic ways to wear a pillbox and both are correct. For a contemporary look, set the hat towards the front so the front edge sits an inch or two above your eyebrows, then tilt it slightly to one side. For the 1960s silhouette that Jackie Kennedy made famous, position it further back and centred on the crown. As a rule the hat should sit at a confident angle rather than flat and level, which is where Sinatra's advice earns its keep. If you wear a side parting, angle the hat down towards the fuller side of your hair for balance.
How to keep it secure
- A fine elastic hidden under the hair at the back holds most pillboxes comfortably for a full day.
- A small comb stitched into the lining grips a lightly backcombed section of hair.
- A traditional hat pin passed through the sides and your hair adds security in wind.
- An updo, a chignon or a low bun gives the hat a firm base and reads beautifully with the shape.
Who a pillbox suits
The pillbox is one of the most widely flattering shapes we make. Because it sits high and adds a little height, it lengthens the face and suits round and heart shaped faces especially well. Longer faces look wonderful in one too, worn tilted forward to shorten the line. It is a gift for anyone who finds a wide brim overwhelming or who wants their face and eyes fully visible, and it works with glasses because there is no brim to compete with the frames. Petite wearers love the neat scale, and taller wearers can carry a slightly deeper block with ease.
Styling a pillbox for weddings and Royal Ascot
For a wedding, a pillbox in a colour drawn from your outfit looks considered and quietly grand, and a piece from our veiled hats adds romance for a mother of the bride or a guest who wants a touch of drama. A birdcage veil over a pillbox is a timeless combination that flatters almost everyone.
For Royal Ascot the pillbox has a practical advantage. The Royal Enclosure dress code asks for a hat or a headpiece with a solid base of at least 10cm in diameter, and a pillbox comfortably meets that requirement. Fascinators are not permitted in the Royal Enclosure, though they are welcome elsewhere on the course, so a structured pillbox is a reliable choice if you want to be sure of the rules. Browse the full pillbox collection to see the shapes and colours we make.
Made to your measurements
Every hat is hand blocked in London and made as a one of one, so no two are quite alike. If you have an outfit to match, our bespoke service will match the exact colour from a photograph or swatch and shape the block to your head. Bespoke commissions take six to twelve weeks. UK delivery is complimentary and worldwide orders are sent fully insured. Founder and maker Monika Perlinska worked as a principal designer in the atelier of Philip Treacy and spent seven years as head milliner at Jane Taylor, making hats for royal families, and that discipline goes into every pillbox that leaves the studio.
Questions people ask
How do you keep a pillbox hat on your head?
Use a fine elastic hidden in the hair, a comb stitched into the lining or a hat pin, and give the hat a firm base with an updo or backcombed section. A well fitted pillbox stays put through a long day.
Where should a pillbox hat sit?
Either towards the front, an inch or two above the brows and tilted to one side, or further back and centred on the crown for the classic 1960s look. It should sit at an angle rather than flat.
Who does a pillbox hat suit?
Almost everyone. It flatters round, heart shaped and long faces, suits anyone who finds wide brims heavy, works with glasses and looks elegant on petite and tall wearers alike.
Is a pillbox hat allowed in the Royal Enclosure at Ascot?
Yes. A pillbox has a solid base wider than the 10cm minimum the Royal Enclosure requires, so it satisfies the dress code where a fascinator would not.
Can I have a pillbox hat made to match my outfit?
Yes. We match any colour from a photograph or fabric swatch and block the hat to your head. Bespoke pieces take six to twelve weeks.
To begin a pillbox in your colour, or to talk through a shape for your occasion, make an enquiry and we will help you choose.
