During this year’s summer lull, we’re going to look at a number of royal hat topics and events we can’t get to during busier times in the royal calendar. This will include a few looks back at Ascot hats, starting today with all those worn by the late Princess Diana. Over the 11 years of her royal life, Princess Diana wore made 23 Ascot appearances in 22 different hats.
1981: Four John Boyd designs including a white veiled hat (the under the chin veil is unique, isn’t it!) and prim tomato red hat with velvet hatband and large white flower at the back, both with short brims. A wider brimmed cream straw small-scale bergere with peach carnations and lilac straw hat with ostrich plume wrap round out the hats Lady Diana wore in 1981, a month before her wedding.
Embed from Getty Images Embed from Getty Images Embed from Getty Images
Embed from Getty Images
1982: Pale pink silk-covered hat with cuffed brim trimmed with a side ruffle by John Boyd in 1982, just before Prince William’s birth
1984: On a Canadian tour during Ascot 1983, she returned in 1984 while expecting Prince Harry in a hat with rounded crown covered in the same dotted peach silk as her dress, with a wide cream transparent crin brim.
1985: A bolder black and white hat with asymetrical brim and a repeat of the peach silk and cream crin hat from 1984 with a view of it’s fantastic brim.
1986: A streamlined cream straw wide-brimmed boater with pleated hatband; a graphic white hourglass shaped hat with black domed crown and bowed hatband; and another of the trendy polka-dot ensembles she wore that year, this one in high contrast jade and black with a dotted silk covered crown and wide, black straw cartwheel brim.
1987: Even bigger brims! A cream picture hat with pale bow and floral trim on June 16; a vibrant blue design with ruched hatband and large bow on June 17; and a white picture hat with kettle brim and navy hatband by Philip Somerville on June 18 (while unconfirmed, I suspect the first two were Somerville designs as well).
1988: A striking straw hat with striped black and white brim on June 14; more polka dots, this time in black and white on a wide brimmed design with slim black hatband on June 15; and a white Philip Somerville hat with rounded crown and wide, gently upturned brim on June 16
Embed from Getty Images Embed from Getty Images Embed from Getty Images
1989: Dramatic electric blue ruched turban with oblique white brim and feather trim on June 20; a wide brimmed pink picture hat with pork pie crown and upturned brim at the back on June 22
Embed from Getty Images
Embed from Getty Images
1990: Two Philip Somerville designs- the purple “pagoda” hat with red hatband on on June 19 and a pale pink straw Breton with tall, upturned brim edged in a wide purple stripe on June 20
Embed from Getty Images Embed from Getty Images
1991: Wide brimmed black straw hat with upturned kettle brim and wide silk hatband on June 18; A textured hat in natural straw with square crown and kettle brim lavishly tucked with silk flowers in shades of pink and cream on June 19
1992: A navy straw lampshade hat with wide mint stripe around the brim, hatband and twee bow on June 16; a high-contrast fuchsia straw picture hat with graphic black hatband and stripes around the upturned brim on her June 17
I’m struck by a few things here- first, is the slow increase of brim sizes during the mid 1980s until 1987, when they really couldn’t have been any bigger! The small hats she wore during the first years of her marriage were quickly replaced by larger designs- not surprising, I suspect as she honed her style through her early 20s. From 1985 forward, there’s a breadth of shapes, styles and colours here, many of which require a fair bit of confidence to carry off. It’s a bolder group of hats than I expected.
What do you think of Princess Diana’s hats worn to Royal Ascot?
Royal Hats 
The turban hat that she wore in 1989 was by far one of my personal favorites for her. She was a stunning woman
I’m sorry, but I thought one of the rules for discussing royals on here was that we weren’t allowed to post inappropriate or personal remarks. I can’t help but notice a post from someone saying they were never a fan of the late Princess Diana’s has been allowed to remain, yet people posting critical comments about Meghan during Trooping the Colour were warned and even banned in some cases.
Feel free to review the Royal Hats Comment Policy.
I’ve reread the comments here and nothing feels inappropriate or disrespectful. That wasn’t the case at Trooping the Colour and I acted accordingly. There is some subjectivity in this- if there’s a particular comment you wish to bring to my attention, reply to that comment or send me a direct message. While I do keep my eye on the comments, I simply don’t have time to scrutinize every one.
This post is a good illustration of how her style (and those of the times) evolved. They are all lovely hats and lovely on Diana. The only one I really have a visceral dislike for is the turban hat. I think if there was some bit of her hair showing I might like it a little better, but probably not. That red & white outfit in 1981 was the bomb to 18 year old me. I cobbled together something as similar as I could and thought I was the bee’s knees going to work at Macy’s on a Saturday LOL Loooooove 1987’s blue cartwheel brim with the yellow print dress and 1988’s white hat with the grey & white coat dress. The yellow is peak Diana playing with color and The grey & white looks so elegant to my eye. Like others have said, the floral one in 1991 was great on her, a great shape and since most of her hats were trimmed very simply this one stood out. What really strikes me from that year though is how HAPPY both she and Sarah look.
My favorite Ascot hat worn by Diana is from 1991 with the flowers in the rolled brim. I loved it the first time I saw it back then and I love it today. It’s simple, classic and feminine. It’s the perfect size. The suit she wore that day is a lovely pale yellow and ivory ensemble that is still very fashionable!
I love the electric blue turban-hat too! A dramatic yet flattering look, with well-selected colours.
I feel it was possibly not to Pss Diana’s advantage that her life in the royal spotlight was largely during the 80s. But who knows? Perhaps in another few decades the 80s look will once more seem ultra-chic…
Love this post!!
Sadly it seems all to evident she wasn’t happy in the last year she attended.
What a great retrospective! Those early hats when Diana was finding her style were sweet in a way. She really didn’t do the Ascot thing as well as she could have, given her much better hats and outfits that I can think of off the top of my head. I always hated that pink and purple hat and think it looks like an inverted umbrella. I know at the time a lot of people hated the turban because it covered her hair, but I thought it was one of her most chic looks. I love the whimsical nature of the straw hat with the flowers tucked in the brim–that seems like an Ascot hat to me. The 1987 yellow flower print dress was very odd for her and if I remember right she never wore it or the hat again did she? Other than those standouts, the rest were pretty basic and were nice enough, although I’ve always felt Diana tried to not wear something new or too outlandish for this event–maybe because she got a lot of criticism for spending on clothes?
I loved these hats at the time – I remember how much I enjoyed noticing Diana’s hats, and they really brought about a bit of a hat revival at the time (following on from the 1970s, hats had become less common at weddings etc, and I think that trend was reversed partly due to Diana).
A comment was made about these hats being dated. I don’t think I agree with that. I think they are not the height of today’s fashion, to be sure, but many if not most could be worn as classic looks even today, particularly because they are on the whole very simple with not much trim, as has been pointed out. I think the 1980s were different in this respect from preceding decades – so many 1960s and 70s hats are “dated” in that one looks and know when they were worn. The difference is encapsulated for me in the Queen’s hats for Charles’ and Andrew’s weddings. The hat for Charles was a left-over 1970s hat, whereas the hat for Andrew, only five years later, was a real timeless classic.
I still think these are very handsome hats, taken as a whole. I do have some favourites: the peach one with the crin brim, the one with the polka dot brim, and the pagoda hat – that whole outfit was striking.
So many hats! that’s quite a bit of work — thanks HQ for putting them all together, it’s really convenient to view them this way.
I found two more; they aren’t on Getty Images. I am not sure if the dates attributed are correct (I think the archivists who label these pics are often inaccurate).
Black hat, Ascot 18?June 1991:
https://www.shutterstock.com/editorial/image-editorial/royal-family-racing-at-royal-ascot-1991-princess-diana-dead-81997-at-ascot-the-princess-of-wales-in-a-white-suit-with-black-widebrimmed-hat-and-matching-twotoned-bag-1119992a
Black and white hat, Ascot 1992:
https://www.tatler.com/gallery/princess-diana-royal-ascot
Whatever one may think of Diana’s outfits, she knew how to wear a hat. And once she had left behind the intricate, draping, flowing garments of the early ‘eighties, and adopted clean structural lines and uncluttered necklines as fashion moved on, in her millinery she also shifted from small dainty embellished hats, to plain, often large, hats which made a simple, bold structural statement .
It was a style formula which happened to suit her to a T. What stands out for me is how little added trim is used in those large hats — occasionally a single bow — when compared to today’s millinery fashion. While simple classic hats with little embellishment never go out of style and can be found in any era, for the last decade or so it seems to me that there is a greater emphasis on trim as the main styling feature of millinery,(e.g. fascinators) than in Diana’s time.
For example, compare Diana’s hat style 1985-1997 with that of today’s Duchess Catherine; I was thinking just recently, will we ever see Kate wear a wide-brimmed hat in summer (aside from her black “memorial service” straw one)? she seems very at home with her medium/small styles.
PS I like the blue and white turban hat too! very chic, reminds me a little of Sheikha Moza.
mcncln, I’ve changed the links in your comment because hotlinking photos is not considered copyright compliant. When we share photo links, it’s really important that we link to the photo’s original source (with photographer credit) or a news article that names the photo source. I’ve replaced your links with links to the same photos that follow these guidelines.
Thanks for these additions- I did some digging on the second photo because something didn’t add up (Diana’s hair was shorter and curled differently in 1992) and it turns out this was actually worn in 1986. I’ve updated the post with both hats.
So… that’s 24 hats worn to 25 Ascot appearances!
Hotlinks, oops! I do know better, I guess I lost focus somewhere along the line…. probably experiencing Stendhal Syndrome due to viewing so many lovely Diana hats in one go. Thanks for fixing the links, HQ. And well done on tracking down the correct date for the black-and-white hat.
I LOOOOOOVE the turban!
This turban is getting a surprising amount of love!
I also love this post! There are many more wide brimmed hats here than I thought there would be. I love the straw hat with flowers in 1991 and the first white one in 1987 (that jacket is so 1980s!) with the curved brim. I don’t remember seeing the pink hat in 1989 ever before and its beautiful!
Here’s a view from the back.
Embed from Getty Images
What a wonderful post on a wonderful Princess! Thank you Hat Queen!
I have always been partial to the John Boyd white hat and veil she wore in 1981. It was so “Lady Diana” and she looked so sweet. The lilac straw hat is so lovely and summery.
The 1987 cream picture hat is so lovely and could be worn today. Really a timeless piece.
1988 was really streamlined. I adore all three hats and looks. I particularly like the hat with striped black and white brim. The entire look is very breezy/summery. Very chic! The polka dot hat is very much in tune with her style, and the Phillip Sommerville hat is a classic that pairs well with her dove grey coat (I think she wore this outfit to the current Earl Spencer’s first wedding a year later).
The straw hat with flowers tucked in in 1991 is perhaps my favorite of her Ascot hats. It’s so perfect for the races and she looks so beautiful in it. I also love seeing her and Sarah, Duchess of York at Ascot laughing and having the time of their lives.
I love seeing Princess Diana’s transformation from soft colors, and hat shapes to bold over the years. She really built up her confidence and it shows in her lovely fashion choices.
I agree!
Boring, never a fan of hers and her clothes and style is/was boring.
Bit harsh! You might not like her style, but boring it was not!
Okay, so this might be my favourite post ever. I have many notes…
I kinda her love her 81 looks. That red and white is such a funny look and yet I loved it at the time. And with better styling (sleeker hair for sure), that lilac cartwheel hat could be stunning.
After that the looks are very sleek; brims go large and then shrink, design features get honed (the turban and the pagoda are beautiful), and yet by her final ascots, I find the outfits all a bit meh. She would be acing Ascot now.
Lovely to look back in very fond memories
I did not know she’d repeated the peach with the see through brim at Ascot. It had a Trooping outing too. She got her money’s worth there.
1987 was peak Di and Fergie mania, and I devoured Ascot that year. I was 12, God knows what my parents were thinking! I absolutely loved the yellow dress with the blue hat, but I remember it wasn’t a popular choice at the time
Really weird; this post got all jumbled. The last two Paragraphs were meant to go after para 2!
She always looked so beautiful! It’s funny how her clothes became more sleek and less “fussy,” but her hats kept getting bigger!
This is a great gallery of Diana’s Ascot hats. She was always stunning!
This is a wonderful post – many of you know what a Diana fan(atic) I am! Thank you, HatQueen! I am about to leave on an overnight train, but I will be back to comment on individual hats on the other side.
Three quick comments now –
1984/1985 – I knew she had remodeled that peach maternity dress for regular wear, but never realized that she wore it to Ascot both times, and two years right in a row!
1986 – the jade/black dotted hat and dress were later loaned or given to one of her sisters – I’ll see if I can find a photo so we can do a “who wore it best”.
1991 – amazing that this is one I have never seen before!
Her first year at Ascot was a real winner. For someone so new to the scene she had a definite look that suited her beautifully. The grey overcoat dress in 88 was one of my all time favorites as is the color blocking in the “pagoda” outfit. As for the hats, I always loved the first one pictured, the blue turban, and the flower filled brim.
What fun to view these all in one collection! I am glad she removed the bow from the dotted peach after Harry’s birth.
Looking at the swirl on the overlapping brim, I think the placement of the bow would be in the back on the second photo- not sure if it’s there or not but I think it’s a better place for it to be!
All things considered I enjoyed how she progressed with style and was willing to do so. Wonder what she would wear today.
I find that by and large I don’t care for Princess Diana’s hats (mostly because I didn’t care for the general hat proportions in the 80s), however there are several here I really like. In reverse order– the mushroom brim from ’92 is fabulous (And I feel like it would look great today- it kind of reminds me of something the Countess of Snowdon would wear). The turquoise from ’87 is really great- that whole look is just super sharp. That kind of echos the boater resurgence we’ve seen in the past couple of years and reminds me of the Countess of Wessex’s large pink ascot hat from last year. Finally, I really like that first one with the under the chin netting. That felt like a brave and interesting choice and one that I think was successful. A very modern take on the Edwardian tie-under-the-chin but large brimmed hats.
This should be a fun series!
The turban one is really dramatic! I wonder if she got any flack of how unusual and daring it was. Most of them seem horribly dated, but I do also like the B&W polka dot from 1988 and the lampshade from 1992.
What an excellent collection to see altogether in one post. Thank you, Hat Queen. With the exception of the 1981hats, I am surprised at how non dated they are. There are a number of these that I can see worn by today’s royals, perhaps at a different angle and with slightly different emphases in the designs. My clear favourite, is the purple “pagoda” closely followed by the peach 84/85 wide brimmed hat. Least favourite probably the white net effort from 1981 or the jade/black polka dots from 1986