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 Hat

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

Hats & Horseshoes 2016 Queens Plate

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

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

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

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
Photo Credit: Dean Villafuerte

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 Hat Race Begin!


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

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 exactly what I’m looking for.

1930s Toy Tilt Hat, Straw Fascinator
Source: Etsy

Stylish vintage 1930s tilt hat.

1930s vintage hat
Source: Etsy

1930s Quirky Tilt 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 (click on image for more views of this hat).

1940s tilt hat
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
Source: Etsy

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

 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.

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?

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 50s Floral skull cap.

Vintage 50'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..Want so bad….

1940s vintage style tilt hat
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.

Liz 🙂

14 comments on “Vintage Hats for Horse Race Events”

  1. OMG! I have to admit although I wear a lot of hats–mostly in winter here, alas, I have never been to a horse race. Mores the pity, I know.

    You have completely inspired me with this collection of hats. I tend to keep my hat collection fairly conservative, but I think I will need to branch out!

    From the hats you found, I could not chose, one, but the cherries one is killer diller, but the green one says horse races to me. Okay, I’ll take ’em all.

    Thanks for sharing this delightful hat fest!

  2. You looked wonderful, as did all your friends. Love the colour of your dress. These hats are amazing, I like the 1950’s fruit and the one that is an explosion of brown net.

  3. What stylish and classy people you and your friends are! Your 40s hat is perfect for the races and I love the others you’ve chosen too. Some great hats. I would have to go quirky, just because how often do you get an excuse to go really quirky?

    • Ahhh thanks so much! Well you for sure have the ability to go quirky that is for sure. I wanted something with a flamingo on it, but I did not have the talent or the time to make something (more like the talent lol)

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