The Tootsie Rollers at Royal Ascot Ladies Day 2015

Following the success of the commissioned hats I made for the Tootsie Rollers to wear to last years Royal Ascot (see here), I was thrilled to work with them again this year. The Tootsie Rollers are a fun all female vocal group with a strong vintage and retro style. Their style is synonymous with the style of the 1940’s and 1950s and Ascot racecourse employs them each year to entertain the racegoers over the five days of Royal Ascot. During Royal Ascot the girls require a total of thirty hats (my kind of girls!) and this year I worked with them to create their hats for the most ultimate day of hat wearing; Royal Ascot Ladies Day.




Earlier in the year they told me about their plans to base the look for each day at Ascot on an iconic vintage film star. For Ladies Day they chose Marilyn Monroe and intended to wear white dresses reminiscent of Marilyn’s famous look. I then set to work designing a set of six hats for the prestigious day, specifically based around hats that Marylyn had worn in the 1950’s. Marilyn is a fabulous style and beauty icon but she is not especially known for donning a hat. After a little research I found some beautiful images of her wearing neat little pill boxes, elegant berets and chic little perchers. All styles that not only met the Tootsie Rollers size requirements but would also contribute to that immaculate feel of 1950’s ladies fashion.       



The Tootsie Rollers usually all wear identical hats, but after a discussion we decided break tradition and opt six different hats. The six hats still needed to work together as a collection so I suggested each hat was made with the same duchess satin, had black accents, was of a similar size, incorporated merry widow veiling and was of course typical of that era.  

I made the suggestion that each hat could include black accents to give the pieces definition as the girls were planning to wear all white. Coincidentally Black and White are of course the traditional colours to wear to the races.

The Tootsie Rollers stylist Joanna Femi-Ola paired the outfits with Lulu Guinness bags, ASOS dresses, Tom Davies Sunglasses, Carat London Jewellery and Cleo B Footwear. 

Above: A Pill Box Hat in production


Above: Lisa wears the finished pill box hat from the above photo with merry widow veiling and black diamantes. 


Above: Flo wears a Duchess satin feathered beret with veiling and rhinestone details. 


Above: Katy wears a very vintage style band fascinator with veiling and diamante detail


Above: Khiley wears a satin pleated beret with diamane jewellery, veiling and Swarovski beads 

Above: Meg wears a black and white polka dot saucer hat with veiling


Above: Anna wears a black and white polka dot pill box hat with merry widow veiling bow featured at the back of the hat


I received fabulous feedback from the girls saying that they were thrilled to receive them, had a wonderful time wearing them and received a lot of compliments throughout the day. 



All of the pieces are now going to be added to The Libertarian’s hire collection. I’ll be making a few tweaks here and there on two of them, but they will be available for you to wear with your own vintage styling! I would love to see what you would wear them with- perhaps little white gloves and tailored pencil skirt suit? I feel a vintage style-off coming on...