The Art of Wearing a Hat, Style File Friday

In honour of the Royal Wedding happening tomorrow (or has already happened, depending on when you are reading this), I’m sharing my thoughts on the art of wearing a hat. Millinery is an elegant and timeless way to elevate an outfit, and add a certain level of chic that can otherwise be difficult to achieve for a daytime event- it can be a big step to get started but once you do, it is a wonderful accessory. It’s also just a lovely throwback to a mostly-gone era where you dressed to the occasion, and embraced the formal!

The Art of Wearing a Hat (1)

Unfortunately, my invitations to the last few royal weddings have not been forthcoming (I’m not too sure why….), so I don’t get to wear my millinery pieces as often as I would like. I usually take any opportunity I can to wear them, usually teas or wedding showers. Typically elsewhere in the world, hats are worn to weddings, baptisms/christenings, the races, and several other events (pretty much everywhere but Canada and about 2/3 of the United States), and I love the statements that they make.

To quote infamous milliner Philip Treacy, “hats always look much bigger off than on”, so don’t be afraid to try something and give it a chance, even if it seems a little large and “out there”! Unless it is actually a diorama type hat, that you see at the Kentucky Derby and Royal Ascot, you probably aren’t as noticeable as you think, and it will provide a nice finishing touch to your ensemble! (If you are looking for a fantastic guide to choose a hat, this article is chock-full of history, quotes, and advice!)


People will often comment that I am a “hat person”. While I am thankful to receive that compliment, I think that anyone can be a hat person given the right hat! A lot of it, I think, is confidence. I wouldn’t say that I am necessarily a confident person, but I am typically not overly doubtful of myself, either, but any piece of clothing or accessory will look odd if you aren’t comfortable and confident in wearing it. With hats, I tend to just remember that people covered their heads for centuries and it’s only very recently in this dressed down society that we live in that hats are eschewed in favour of “easy”.

A few tips for buying and wearing hats:
1) Look on Etsy- you can often find vintage and/or pieces made by up and coming milliners that aren’t as expensive,
2) When you are purchasing a piece of millinery, ensure that you do in fact own something to wear with it,
3) If you are new to millinery, I would recommend either your millinery or your clothing in a neutral colour,
4) Balance your hat with the shape of your clothing, much like you would the rest of your clothing;
5) Try on as many pieces of millinery as you can to get a feeling for what you like and don’t like on yourself,
6) Remember that wearing a hat should be fun and enjoy it!


Do you ever wear hats? If you do, what style is your favourite?

Until tomorrow,
The Historian
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20 thoughts on “The Art of Wearing a Hat, Style File Friday

  1. HistorianRuby May 18, 2018 / 2:50 am

    I’m really not a hat person but then I don’t go to many events that require them. My grandmother (died 1963) never felt dressed without her hat and would say on leaving the house ‘I need to put my lid on’.


    • anhistorianabouttown May 19, 2018 / 5:11 am

      I’m starting to get the way with hats- it really does finish an outfit! I wish more events required hats, I think it really makes an event special ☺


  2. tahenryauthoress May 18, 2018 / 8:49 am

    I LOVE hats. I used to wear them more when I lived in Cali. They all had to be the big and floppy variety to prevent sun burning there. Sadly, it’s not as functional here. No sun. LOL
    I love the old 40s hats though.


  3. You Can Always Start Now May 19, 2018 / 4:39 am

    I like hats and it is too bad we don’t wear them more often. For me it has always been too much (thick) hair when I try hats on for fun they never seem to fit over the mess. Wedding hasn’t happened yet for me. Will be fun seeing the hats.


    • anhistorianabouttown May 19, 2018 / 4:44 am

      I’m loving watching all of the arrivals- there haven’t really been any standout hats for me yet, but there is still time! Amal’s canary yellow ensemble is beautiful, but I don’t think her headwear is one for the ages for me


  4. Kelsey @ There's Something About KM May 19, 2018 / 5:16 am

    I never considered Etsy for buying hats! I’m not big on hats for myself, but then again, I’ve never really found “the one” so I’ll keep trying. 🙂


  5. arv! May 19, 2018 / 5:48 am

    Hats were never used by females in India since ancient times. We had a very different system for women to cover their head. It involved using a cloth to cover both head and upper body. In a way, it is completely different from the western system. By the way, You are looking great with that hat!


    • anhistorianabouttown May 20, 2018 / 7:24 am

      Thank you!! I do find the history of headwear quite fascinating, as it tends to change and evolve across both geography and time- interestingly, it can look very different but all stems back to covering women’s hair 🤔


  6. Snuffy May 19, 2018 / 7:18 am

    I am a ball cap kind of person and have been told I look good in them. I have a few other nicer hats (including a fun red one) but never think to wear them as an accessory before heading out the door. Maybe a bit too worried about “hat hair” I suppose!


    • anhistorianabouttown May 20, 2018 / 7:23 am

      I actually avoid baseball caps, because they are the only hat that gives me hat hair haha! I think that some people can just pull them off for a lovely casual look, and I wish I could!

      Liked by 1 person

  7. Lisa Orchard May 19, 2018 / 9:35 am

    What an interesting post. I’d love to learn more about the history of the hat and it’s evolution. I’m kind of a closet history buff. LOL! Great pics and I love your hat!


    • anhistorianabouttown May 20, 2018 / 7:22 am

      I am actually starting up history posts in June, and the history of hats is pretty high on the list haha (go figure)! Thank you so much 😊

      Liked by 1 person

  8. josypheen May 19, 2018 / 12:47 pm

    I blooming love that hat! You look sooo lovely! 😀


  9. Channon Gray May 19, 2018 / 5:23 pm

    This seems like the best day to be talking about wearing hats considering it is the Royal Wedding! I hope you had it on in celebration! ❤


    • anhistorianabouttown May 20, 2018 / 7:20 am

      Haha, it really was the best day! And I wore it for hours haha, as I don’t have many opportunities now 🤣


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