This Past Sunday I attend my 3rd Hats and Horseshoe event at Woodbine Racetrack in Toronto for the prestigious 157th ‘Queens Plate‘. I wore one of my favorite 1940s Vintage hat that I had previously worn the first time I attended this event (but with limited pictures) so I thought I would give it a spin again with a different outfit. Here is the hat with my gorgeous friend Steph and her Hat.

Hats & Horseshoes 2016 1940s Vintage Hats - Vintage Fashions Inspiration for Women

Before I get into the post I wanted to share some images from that day of my well dressed Toronto Vintage Society Friends & Family (My parents are on each end of the image).

Hats & Horseshoes 2016 - Vintage Fashions Inspiration for Men & Women
Hats & Horseshoes 2016 Queens Plate - Vintage Fashions Inspiration for Men & Women

This lovely couple of friends pictured below, are very talented sewers and tend to make all their own outfits for their adventures. Andrea created this outfit (the hat she made herself) as an ode to My Fair Lady and you can read all about it at her blog ‘PhysicsGirl on the Loose‘.

Hats & Horseshoes 2016 Queens Plate. Vintage Fashions Inspiration for Men & Women

The hubby and I. My dress is 1950s Vintage from Flash Back Vintage in Toronto, my vintage Lucite basket-weave purse was purchased (after 4 years of dreaming about it) from Cabaret vintage. Hat vintage 1940s from a friend and vintage Lucite ‘L’ pin from the Toronto Vintage Clothing Show.

Hats & Horseshoes 2016 Queens Plate - Vintage Fashions Inspiration for Men & Women

3 of the guys made it into the Top 10 of the Best Dressed Men’s Comp (#82 #21 & in the blue suit with boater).

Hats & Horseshoes Queens Plate 2016 Best Dressed Mens Competition - Vintage Fashions Inspiration for Men & Women

And another friend (#62) made it into the finals for the women (there were around 160 entries that they brought down to 60).

Hats & Horseshoes 2016 Queens Plate - Vintage Fashions Inspiration for Men & Women
Photo Credit: Dean Villafuerte

Vintage Hats Inspiration-What One Could Wear to a Horse Race Event (or any event)

Now on to today’s post. I was so inspired by what I saw at the race and by the image below that I thought I would scour the internet for quirky and beautiful vintage hats that one could wear to a horse race event.

Let the Vintage Hat Inspiration begin!

Disclosure: Some of the links on my blog from Etsy , eBay, are Affiliate Links, meaning, at no additional cost to you, I will earn a commission if you click through and make a purchase. 

Note: If you click on an item and it is no longer available, don’t fret! The websites provided are updated daily with 1000’s of products, so you are bound to find something that will work.


Vintage Shopping: I have created an Etsy Collection of Vintage Hats that would be perfect for Easter or any occasion. It is updated monthly.


1930s vintage photo of the Madcap Millinery at the 1939 Ascot Races. Stunning 1930s hat inspiration!

This 1930s vintage hat SCREAMS Horse Races does it not? I love the Lucite oriental hair stick on the front.

Vintage Hats: 1930s art deco vintage straw hat

Vintage toy tilt hat from the 1930s or 1940s in black and white, made by Austelle. I love the train and the bow at the end that keeps the hat on your head. Small and cute and a bit quirky.

1930s Vintage Hat: 1930s Toy Tilt Hat, Straw Fascinator
Source: Etsy

Stylish vintage 1930s tilt hat.

1930s vintage hat - 1930's black tilt hat with flower motif.
Source: Etsy

1930s Quirky hat to the max! This will get you noticed, that is for sure.

1930s vintage tilt Hat
Source: Etsy

Because I love Cherries- 1940s Tilt hat with Cherries and a cool top knot.

1940s vintage hat: 1940s tilt hat with cherries.
Source: Etsy

Horse Race Hat WIN! This 1940s “peek-a-boo” hat will get you noticed, fall in the quirky category and keep the sun off your head and that colour…gorgeous!

1940s Vintage Hat: 1940s Red "peek-a-boo" hat
Source: Etsy

The green in this 1940s vintage hat makes it so unique.

 1940s vintage hat: 1940s 'New York Creation' tilt hat in chartreuse green
Source: Etsy

Oh my goodness…..Vintage 1940s hat, blue straw tilt. This is simply marvelous and super fun! And my absolute favorite so far.

1940s Vintage Hat: Vintage 1940s hat, blue straw tilt with polka dot ribbon
Source: Etsy

Dior’s New Look is excellent for making a statement when you head to your seat. The brim reminds me a bit of the song “Surrey with the Fridge on Top” from Oklahoma, don’t you agree?

1950s Vintage Hat: Vintage 1950s hat
Source: Etsy

I find 1950s hats could sometimes head into the most interesting direction with their styles, like this lovely AND Quirky 1950s Floral skull cap.

1950s vintage hat: Vintage 1950's orange and green floral skull cap.
Source: Etsy

As I end the hat section I’m going to post my bucket list hat which is actually not vintage at all, but is just so stunningly beautiful. Sigh..1940s vintage style tilt hat.

1940s vintage style tilt hat - Black and Off-White Striped Pillbox Fascinator Hat - 1940s Style - Velvet &Taffeta Fabric
Source: Etsy

Lastly, For a great blog post that showcased many of the hat styles seen at the Queen Plate this past Sunday, check out the blog ‘Hats by Anne‘. You just might see myself in there as well.

Question Time: Would you go with Quirky or Elegant for a hat to the races? Or maybe you would combine the styles together? Let me know.

FURTHER READING:

Liz 🙂