Guest Post: Planning Your Outfit for Royal Ascot Part 2

 It’s my pleasure to again welcome Polly Singer, milliner behind Kentucky-based Polly Singer Couture Hats, to Royal Hats for a continuing look at her process for choosing a hat to wear to Royal Ascot. Thanks for joining us, Polly!

As I mentioned yesterday, I like to have one outfit and a back up for big events. Here are my second set of options for Royal Ascot next year.

Through Instagram, I started following Suzannah, a British luxury brand designed by Suzannah Crabb.  She dresses members of the British and European royal families (the Duchess of Cambridge, Princess Beatrice, Autumn Phillips, Zara Tindall and most frequently, the Countess of Wessex) as well as A-list celebrities. The boutique is based in London, the design style is vintage couture and the fabrics are to die for. Their dresses are an investment but I am one who keeps my clothes forever.

I chose a solid color, the Aimee Dress and Capelet in Emerald Green. As a redhead, I love this color, it works well with my complexion and I have nothing in this shade at present. The cut is breathtaking and I love the capelet, which covers the top half of the arms. I am one who likes being covered up!

Now to choose a hat!

Hats #1 & #2:  Drina or Greta – this was my first idea when I saw this dress.  The colors would work seamlessly.

Hat #3: Vivien – A larger hat but very dramatic and a nod to the “Ascot Opening Day” scene in My Fair Lady!

Hat #4: Marilyn – An easy choice.

Hat #5: Miss Peacock – The peacock feathers bring in the green and the royal blue is stunning against the emerald green dress.

Hat #6: Mitchell – Different but a good choice.

Hat #7: As you have probably noticed, a solid color dress gives you much more freedom in selecting your outfit. If I take the Carlisle Collection foral dress and coat with me in addition to Suzannah dress, I could wear the solid white hat for both options.


As a designer, working alone, It’s important to get feedback.That helps me get a good idea of what people like!

It’s time for feedback, dearest readers- Polly and I can’t wait to hear your thoughts on which hat you think works best with this fabulous green dress. Share your observations and cast a vote below on what you think Polly should wear to Royal Ascot next year- pop back to yesterday’s post for another look at the hat options for the floral coat and dress.

Thank you, Polly, for including us in preparations for your 2021 Royal Ascot adventure. We’ll have to check in next June about this experience and see what ensemble you choose!!

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

28 thoughts on “Guest Post: Planning Your Outfit for Royal Ascot Part 2

  1. The winner is….Drina! The hat named after Queen Victoria’s childhood nickname, which was “Drina”. And as you know, was Queen Elizabeth’s great-great grandmother. A truly Royal choice indeed for Royal Ascot! I had to smile at that!

    Thanks for everyone for their ideas and feedback. You all are amazing!

    Lots of love, Polly

  2. How dreamy to have a whole studio of hats to pick from, Polly! Sheer styling heaven. Thanks for sharing your outfit ideas with us, these posts are so much fun.
    Ascot’s motto is surely Go Big or Go Home, so I’m with the majority in favour of the green dress. The floral ensemble is a gorgeously appropriate Ladies Day choice, but of the 2 outfits, visually it is more delicate. The green one is going to really make you stand out from the crowd from afar (as well as up close).
    All your suggested hats are lovely and go with the green dress. However, I would use Ascot to showcase one of the most dramatic and impact-making hats in your portfolio. Below are those hats on your list which I feel are the more low-key options, relatively speaking, (so therefore not my first choice):
    #1 subtle intricate texture/pattern – looks best up close.
    #2 shiny ribbon – so best with shiny accessories. Navy colour not as impactful with green dress as black.
    #4 soft, subtle design.
    #5 small scale.
    #6 medium scale.
    #7 perfect Ascot scale (large). You are so lucky having the height to look effortless in a wide hat. But I feel this hat requires earrings and bag in a third colour/ multicolours since white can be low-key on its own next to the green.
    My choice:
    #3 black-and-white “Vivien”. I love the way it creates large simple blocks of strong colour contrast against the green, which itself is a block of colour.
    To accessorise this I would stick to matte finishes, to match the matte textures of the dress and the hat. I would add:
    > black shoes and black cropped half-gloves (to connect to the black of the hat).
    > a plain white clutch/bag (to connect to the trim).
    > burnt red or orange lipstick and nails (a 3rd contrast), and long, big non-shiny earrings.
    I also love your “Yuki” design, which I think would look just as amazing as the “Vivien”. It has the added advantage of having peach-coloured flowers, which would really highlight your auburn hair.

    • Thank you! Wonderful ideas. I did like the “Vivien” with the large simple blocks of color. I really appreciate the shoes, gloves, bag and makeup recommendations. “Yuki” would work well too! I had never thought of that but the colors complement well.

  3. I have no problem in voting with the majority for the green Susannah dress and the wonderful buntal Drina hat. I love the sleek lines of the dress, and the colour, perfect for a redhead. And it really makes the hat stand out. Would look gorgeous on you Polly! If you take two dresses, you should take two hats (if you can manage!)
    You could save the Carlisle floral ensemble for if it were too cold to go sleeveless (English summers, you never know). And may I suggest you curl your hair, at the bottom? 1940 ‘s film star like, would look drop dead gorgeous.

    • Wies, thank you for your feedback. I do like the idea of two hats. The Carlisle outfit would work well if it were too cold for sleeveless. I love the suggestion of curling my hair at the bottom. Thanks!

  4. I think my favorite statement look would be the emerald green dress with the first hat hat (Drina) paired with royal blue and nude accessories. But I still love the first dress and coat with either the large white hat or the fuchsia one. I did notice that some of the hats are perched on the right side of the head and a couple are on the left side – does that make a difference? Is there a written guide to how the hats should be worn?

  5. Personally, if it was my first time at Ascot, I would go all out since I don’t know when I would get the chance to attend again. The emerald Suzannah dress with the Drina hat is clearly my top choice (many readers here know green is my favorite color). This also feels like an outfit we would see on an actual royal (Countess of Wessex or Princess Haya spring to my mind immediately), so that definitely makes it even more appealing. Most of the others would be great choices, but I think the Drina truly brings it all together and makes for a showstopping ensemble.

    I know I said yesterday I would choose the Gretchen in coral red to pair with the Carlisle Collection outfit (a most beautiful outfit for sure), but if we are choosing for Polly, I think the all white would be best since her auburn hair would make a great contrast to the white. This combo would be my runner-up ensemble choice.

    Looking forward to seeing what you actually decide to go with Polly! No matter what, I’m certain you will look great and will have a fantastic time. Who knows, maybe we’ll be able to feature you with photos from Getty Images? 😀 (I mean that in the best way!)

    • Jake, thanks for your comments. I feel the same way regarding Ascot! That is why I want to go all out! A dream come true. I love green too. I thought the Suzannah with the Drina was a very Royal choice. Featured in Getty Images would be a dream come true! I wouldn’t know what to do! LOL

  6. Polly, your hats are ALL great. This is a super post today, thanks. We may need to pay you a social call, next time the Bourbon Trail is on our calendar!

    Hat #1: My first choice, hands down, followed by Hat #7. (yesterday’s large white)
    Hat #2: I don’t care for the center ribbon – something placed on a present found under the tree.
    Hat #3: Fantastic hat in a different color, (cream?) with a matching green flower? This would be the perfect hat to wear if you forget your umbrella. (only kidding)
    Hat #4: Nice enough.
    Hat #5: My 3rd choice. Very elegant and lovely.
    Hat #6: My last choice. Camilla could wear this to the next Royal wedding.

    Question for all the ladies: From the initial photo of the green dress (Jake will be a huge fan!) I can’t judge how long it is. Does it go far below the knees? Does that play into the choice of head wear, for overall balance issues? Are longer styles dictated by the age of the wearer? Princess Alexandra comes to mind.

    • Haha thanks Jimbo for always calling me out when it comes to green. I hope my love of the color hasn’t become too nauseating. 😉

    • Jimbo, Thanks for your comments. Yes, please pay me a social call next time you hit the Bourbon trail. In fact, my house and studio are just mere blocks from the Royal Spring, which is reputed to be the Birthplace of Bourbon. Not sure on the length of the green dress. I am thinking it is just below the knees.

    • Jimbo as a sometime stylist, I couldn’t resist answering the question you threw out about dress hem lengths. I really did try to make this short (bad pun I know) but failed….
      ~How long is that green dress? based on too many hours browsing online fashion, I would say that the green dress is “well below the knee”. Note: the long hem would be viewed as a flexible feature by many customers, who would expect to get their hems customised/ shortened after purchase.
      ~Age. While rules about fashion, especially “age-appropriate” fashion, have gone out the window, I know from my styling work with young women that the majority of them would be put off by the length of this dress. Midi-length hems are High Fashion at the moment (see Countess Sophie), but the majority of youth want to conform to a distinctly mainstream youth fashion, not High Fashion. So the majority of under-25’s prefer above-the-knee lengths, as can be seen on any youth-oriented retail fashion website. Women older than this tend to be less wedded to youth fashion, and are therefore more likely to consider this hem length; note the hem-length evolution of Princesses Beatrice and Eugenie towards longer lengths.
      ~Practicality. There’s a reason behind a longer hem length for this style of dress (the sheath dress) which is of top consideration for royal ladies, (or any woman who is aware of her presentation). It’s a fact that the narrower the skirt, the longer the hem needs to be. With narrow (pencil) skirts, when the wearer sits down, the skirt will ride up, sometimes well over 12 inches. This can create a serious modesty issue. Crossing the legs is not always a solution — let alone appropriate for a royal. Princess Diana, with her short pencil skirts of the ‘eighties, was adept at the “sideways sit” — but situations like sitting on a makeshift podium, where photographers can take potentially embarrassing pics from below, are a real challenge. The longer-length pencil skirt is an all-round winner.
      ~Hat choice and balance. There are so many factors to this question The wearer’s height, hairstyle and figure, the dress’s colour(s) and its cut, detailing and fabric come into it too. Wide brimmed hats are commonly seen as a great choice with this type of dress, but we only have to look at fashion photos from the 1950s to see that small hats were the more usual choice with this dress style. However 1950s sheath dresses were not made the same way or with the same fabrics as modern sheath dresses (no stretch fabrics for starters), so I think each case needs to be looked at individually.
      ~ A note on shoes: for most women, the modern sheath dress at this length looks most balanced with a dress shoe where the heel is at least 2.5 inches, or higher. If the wearer wants to wear a lower heel, the usual solution is to bring the hem up to just below the knee. The informed wearer will run the “sit test” before deciding just where the hem should end. HM has settled on a classically-balanced hem length of just below-the-knee, paired with a moderate/low heel, for all her day wear. (Her “pencil” skirts are in fact cut slightly A-line, so that they are less inclined to ride up when sitting).
      ~ Princess Alexandra. Her skirt style, like Queen Margrethe’s, mirrors 1950s fashions, where tailored midcalf pencil skirts were worn with low heels. (see Audrey Hepburn, Grace Kelly) The Princess is 10 years younger than HM, but as you can see below, she is wearing her low heels with a hem much longer than HM’s, so longer hems do not equate with age. (To be fair, Alexandra’s skirt is narrower than HM’s, so from a modesty viewpoint only, it does need to be further below the knee than HM’s, but not as much as that). Most senior royal ladies, such as Queens Silvia, Sofia, Anne-Marie and Sonja, Princess Benedikte, wear low heels with their pencil skirts just below the knee, same as HM.
      Embed from Getty Images
      Alexandra has worn shorter hems (in the 1960s) — but perhaps she has a fondness for 1950’s hem-lengths? I would love to ask her (indeed all royals) why they choose one style over another.

      • Mcncln:
        Thanks so much for the great reading! You are clearly very knowledgeable in fashion circles, and I appreciate your wonderful insight.
        I just know what I like, sometimes not even knowing why I like/dislike it. Mrs. Jimbo, while not in her 20s anymore, tends to wear the length just below her knees, which I like. (She has very good looking legs, which certainly helps when deciding a length of dress.) Thanks again.

  7. for me, the beautiful green dress wins hands down. my choice for the hat is todays hat #1drina in green/peacock mix, which goes with the dress and has the ascot drama that will deliver the perfect impact. my suggestion for an up to date look is to accessorise with non-matchy-matchy items across your purse, shoes and any gloves/scarf – yes, go for an item or 2 in electric blue (picked up from the hat), and mix with other accessories in a neutral – i think gold/snake or nude would work best.
    i also really like the large white hat from day 1’s selection, which would work with the same accessories. plus this hat would look great with the other outfit as a reserve…
    whatever you choose, i’m sure you will look amazing. enjoy your day and we look forward to hearing all about it!

    • Sir Lancelot, Thanks for your comments. I like the idea of the electric blue item and the other accessories in a neutral. I really appreciate the help! I can help others pick out things for themselves, but tend to be a bit blind for my own choices.

  8. green susannah frock with hat option #1 for a win. love love love the color and shape of that frock! i could wear that! this is a great post!

  9. the green dress would look amazing maybe opt hat no..3 in green and white and the purse, tiny belt and shoes in red.

  10. I chose the option: Green Suzannah dress with hat #5: Miss Peacock navy saucer with peacock feathers.

    I am not sure about your logistics but hat #5 & navy accessories (handbag and shoes) would match with the green dress. The Carlisle Collection floral coat and dress would match with hat #3: fuchsia sidesweep saucer with feathers & the same navy accessories with the green dress. Less to pack?

    Looking through your website, I would go with Lovely Linda – Limited Edition hat. I think this was worn in the instagram post that another reader posted in yesterday’s post? It looked really good with the Carlisle floral dress. I think it just might work with the green Suzanne dress as well? Navy goes with the green and the hot pink flowers would give alot of contrast. With this pairing, I would also go with navy accessories.

    • Coco, Good choice. Lovely Linda does work well with the Carlisle floral dress. I could try it with the Suzannah dress. The hot pink would provide a nice, unexpected contrast.

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