Guest Post: Planning Your Outfit for Royal Ascot

I am so pleased to welcome American milliner Polly Singer to Royal Hats today. After mastering traditional millinery techniques during study in New York, she returned to her native Kentucky and established Polly Singer Couture Hats. Working by hand with fine materials, she creates each hat as an individual work of art. She also planned to lead a tour to England in June with an itinerary that included Ladies’ Day at Royal Ascot (now postponed to 2021). Polly graciously joins us today to share her process for choosing a hat to wear to the pinnacle of hatted events. Welcome, Polly!

I first fell in love with Royal Ascot while watching “My Fair Lady” as a child. The Ascot Opening Day scene with the clothing and hat designs by Cecil Beaton is a favorite. I designed hats on this theme while attending the Fashion Institute of Technology in New York. For years, black and white were my favorite combination. Classic, elegant and timeless.

Embed from Getty Images

So needless to say, my lifelong love of “My Fair Lady” and hats led me to form a travel company, Elite British Tours.  My clients and I will be attending Royal Ascot on Ladies Day in 2021, in the Queen Anne Enclosure.  It will be the trip of a lifetime for many of us. There are a few spaces open for 2021.

So which is first? The dress or the hat? As a milliner with 27 years of experience, you would think I would have the answer, but I don’t!

Getting the Hat First

Pro: If you get the hat first, you can do most anything color wise and style wise.This really gives you the most freedom of all.  It takes much of the pressure

Con: You must find a dress in your size, style and desired color to make it work. However you can always choose a neutral solid color such as white, ivory, black, navy, gray or even pale pink. It’s the prints and florals that get us into trouble!

Getting the Dress First

Pro:  You are able to get your dress choice out of the way, choosing a dress that you have fallen in love with.

Con: Now you have to find a hat to match it or get one custom made. If you wanting to do something custom, you will need to budget the time and expense accordingly.

My biggest tip:This may sound excessive, but I like to have one outfit and a back up. I find it cuts down on my stress level and gives me greater options. Yes, some call it “over packing”. I call it “insurance”.

Now to my outfits for Royal Ascot 2021! The first outfit option is based on a floral dress and coat that I purchased last year from the Carlisle Collection. You will notice that this dress/coat has a white background with multi colored flowers.

Hat #1: I could choose to do an all white hat, which would give me the greatest flexibility of all.  I can pair that with another dress if I changed my mind.

Hat #2: I could do a custom white hat pulling in a few colors that appear in the dress.

Hat #3: Gretchen could work well.  A solid saucer hat would work with a multi floral dress.

Well, dearest readers, which of Polly’s three designs here do you think work best, with this beautiful dress and coat, for Royal Ascot? Polly and I are looking forward to reading the rationale for your choice!

Stay tuned tomorrow for a look a Polly’s second outfit option, a stunning dress with six possible hats. In the meantime, here is a look at the famous Royal Ascot scene from “My Fair Lady” with what must be the best parade of hats in film. 

Photos from Getty as indicated and from Polly Singer, none of which may be copied or replicated without written permission.

45 thoughts on “Guest Post: Planning Your Outfit for Royal Ascot

  1. You all are great! I truly appreciate the feedback and lively discussion. It forces me to think outside the box. I must admit I was a bit nervous doing this project since I regard you all as experts!

    To give you a little feedback on me, I am 5’8 and usually wear heels. I tend to design big since I am tall. That being said, I can also wear things like the Gretchen red saucer hat, #3.

    Trish’s suggestion of the Carol was a good one. In my quest to design something different, I overlooked that one! That’s what happens when you have so many hats! LOL

    My custom clients tend to prefer designs similar to the second hat. I design mostly for the Kentucky Derby, where more color seems to be preferred. Personally, I prefer monochromatic tones and neutrals. Overtime, I starting adding more color to designs for my clients. The Europeans wear more neutrals and monochromatic pieces.

    The photos above show me wearing what was basically left over in the shop. I had bought the floral coat dress and was determined to wear it, no matter what! 🙂 It usually works that way in the spring since my stock is quickly depleted and that year, it was just me making all the hats.

  2. I agree that hat #1 is too much white with the white background on the dress and coat. I also think bigger is better for Ascot and #3 seems small. I went on Polly Singer’s website and there are some gorgeous hats! What about the “Tickled Pink Tallulah”? It’s big and it’s pink!

  3. I’d plump for the third hat, myself.
    The first hat is elegant, but as it’s just white, I think the coat would leave it in the background.
    The second hat is more attention-getting, but the high contrast leaves the pink flowers looking a bit random and splodgy, rather than part of a ‘pulled together’ look.
    The third hat seems just right, although like some other commenters I find it hard to judge proportions when the hat and clothes aren’t on the same figure.

    • I agree with you Deborah about hat #2 feeling a bit too random. #3 is definitely my first choice. #1 would be a good choice and would work best on someone with dark hair (like Duchess of Cambridge) or darker skin (like Duchess of Sussex or Princess Angela of Liechtenstein) to give some nice contrast in between the hat and outfit; I also think someone blonde and pale could potentially look washed out with all the white around their face.

  4. For years, my only knowledge of Ascot was MFL, so I thought black and white WAS the dress code! It was a stunning scene, but it would be hard to repeat that year after year, so it’s best that the colors are unlimited.

    My vote is for the white hat with the loop and the red flowers, but minus the feathers.

    Thanks, Polly, for the fun post.

  5. Absolutely, the solid saucer in number 3. It compliments the floral dress and coat, and “pulls out” the colors of the flowers. I’m a quilter, so I approach this the same way I would plan a quilt. In this case, a white would serve as a grounding color, but a red would make the floral POP!

  6. Polly, thanks for the wonderful, (bittersweet) post. You have a very nice website as well. If you need an assistant next year for the Royal Ascot, to schlep hat boxes through the airport, give me a call.

    My preference of your three choices is an easy decision for sure.
    WIN: Hat #3 – a great color splash to all the white in the ensemble. The smaller scale is more balanced for my uneducated eyes.
    PLACE: Hat #1 – with the loops or flowers, but not both. Or perhaps smaller, denser flowers?
    SHOW: Hat #2 – this hat would compete with the ensemble. I think there’s too much going on.

    HatQueen, thanks for the movie clip – I haven’t seen MFL in years. Remember when Liza yells at the ‘orse to move ‘is bloomin’ something-or-other? Great stuff, that!

  7. Hi. I would choose the first hat, but I would wear it either with the loops or the flowers, but not both. The heavily patterned dress needs a complimentary hat, not one that competes. I think I’d pare the hat down to just the loops and let the flowers on the dress take the focus. Thanks. Can’t wait for tomorrow’s look.

    • Gigi, Thanks for your comments. Very much appreciated. The heavily patterned dress can be hard to work with. I find that people often pick heavy florals after a long, dark winter…I know I did. But they can be hard to coordinate with.

  8. I like the second hat, though maybe minus the bow, just focusing on the flowers.
    We were supposed to be at the Derby this week. I bought all my hats before dresses, and actually was still searching for a dress for one of them (I found one I loved but it was so expensive – was waiting to see if I could locate it on consignment).

  9. I would go with option #3 with the dress. I think with #1, it might look too much white for the entire outfit?

    I definitely agreed on carrying extra clothing especially since you are flying overseas to attend ascot. It was a nightmare for me when I flew overseas to attend a wedding and accidentally ripped my skirt while putting it on (it was made of very delicate material). Shops didn’t open that early so I couldn’t purchase another outfit for the morning ceremony. Had to turn up in jeans!

    • Coco, thanks for your feedback. Glad you agree with the extra clothing. So many things can happen. That’s awful about the ripped skirt for the wedding. Travelling is nerve wracking at times.

  10. to complete my previous comment, I prefer a solid color with the floral dress. A solid color allows both the hat and the dress to be appreciated on its own. I think the embellished white hat competes with dress. Of the pink and white solid hats, I prefer the white. It’s size complements the dress without competi my with the dress. To my eye, the pink hat is not quite the right color, and a little too small.

  11. Welcome Polly! your tour to Ascot sounds divine, you must be so disappointed about this year — but I hope the 2021 tour will be a great success.
    I think many of us readers of Royal Hats love that scene in My Fair Lady too.
    That is a stunning Ascot ensemble you have chosen, with a fabulous spring vibe. Queen Maxima is wearing something similar here (25 April 2017) too bad we didn’t see her wear it with a hat! Judging by her red accessories, it’s my guess she would vote for you to wear #3 the red saucer 🙂
    Embed from Getty Images
    Princess Beatrice chose to wear a red and white hat with her red and white dress to Ascot Day 3, 2012 — so I think she would vote for #2.
    Embed from Getty Images
    Your hats are just right for the spring and I think any of them would work well as long as the colours are a good match for the outfit. But as the red hat #3 would have the most visual impact (as well as linking the hat to the pattern in your outfit) that one would be my first choice. I would love to see photos of what ensemble you finally wear when Ascot 2021 comes around!

    • I love this dress on Max. Hope she repeats it with a hat someday. Not sure I love this hat on Beatrice, but the ensemble is a good argument for picking up the dress colors in the hat trim.

  12. Oh joy! The MFL Ascot scene is positively my favourite film and musical fragment ever. The costumes are beyond wonderful of course, but I also love the music and the scores. Happy memories for me too!
    Welcome to Mrs. Singer! What a pity your trip to Ascot had to be postponed. Still, the dress and coat are beautiful and will hold very well until next year.

    The three hats are all in the same style: saucer hats worn tilted to the right. So whatever the colour, the general impression will be the same. Only the red saucer is smaller, so maybe a little less “grand” than the white one. Still, as it is red, it will be visible enough.

    Not having seen Mrs. Singer wearing the frock, coat and hats, it is difficult to say. For a lady of smaller size I would recommend the red hat: the big white one might “dwarf” her a bit. But as she made these hats herself, I’m confident she can carry them off equally well!

    My choice would probably be number two, but with some extra pink flowers added. The scale of the hat is Ascot worthy, the white base goes with the white background of the coat and the coloured flower trim clearly indicates “Bespoke”. Very chic!

    P.S. I totally agree with overpacking as a form of insurance, I’ve never been in favour of “travelling light”. Unfortunately we don’t travel with trunk suits on ocean steamers anymore and airline companies charge us heavily for our elegance!

    I’m looking forward to your next outfit Mrs. Singer!

    • I’m in agreement with you Wies about having Mrs Singer wear the outfits. It would give us a better vision in terms of scale.
      At first glance, I like the solid red/pink as it brings everything together, but, for Ascot, I always think “the bigger the better,” so I would choose hat #2. Both are great designs and thank you for this fun post! Please do more!

  13. Thank you for this great post! I helped a friend get wedding outfits for her two children’s weddings. The first one, she got the hat first (neutral colour, statement shape) the second time we got the outfit first and then matched the hat. Both worked, but it was different.

    I really liked all three options. I think I like the customised one least – a multicolour outfit looks best with a solid colour hat for me, unless it was a full on floral bouquet statement that copied the pattern on the outfit! I would choose the pink hat, as it matches so well and pops with with the colours in the coat. If you couldn’t find an exact match with one of the main colours, I would choose the white.

    • This is what I meant by “adding some pink flowers”, but you said it better than me: the floral bouquet should copy, or perhaps complement the pattern on the outfit. Thank you trickymum.

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