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How to Wear a Hat.

People often ask me how to wear a hat. Or they say something like… “I LOVE hats, but heck if I can wear one”.

It’s a complex issue, and I figured it was time I attack it HEAD on, right here. Right now.

Before you click away, convinced that YOU are not a hat-girl, let me ask you this… What would you have done if it were the 1920’s and Carson and Mrs. Hughes had invited YOU to their wedding?

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You would have found a hat that suited you because there is NO WAY in hell you would have missed THAT wedding!! I mean seriously…

All the women in the cast of Downton Abby have different face shapes, hair styles and body types… and they ALL look lovely in hats. If it’s possible for them, it’s possible for you too.

What’s the old proverb… “Saying you don’t look good in a hat is like saying you don’t look good in shoes.” 😉

So, now that I’ve proven YOU CAN WEAR A HAT AND LOOK GOOD DOING IT (you just need to find the right one), it’s time we talk about WHAT IT TAKES to wear a hat.

To be honest, I’m not sure about all of the how-to-find-the-perfect-hat-for-your-face-shape charts you can find online. I swear my face doesn’t fit into any charts, and I’m convinced one must consider more than face shape when buying a hat. But for those of you that are curious, the best resource I found online for finding the right hat for you face shape was HERE on the Goorin Bros website.

Here’s MY advice. Go shopping. Try on every single hat you can get your hands on. If you live near a hat shop like Goorin Bros, go there and ask the experts. If you live in the sticks like me and shopping online is your best bet, then ASK A MILLINER (aka – hat maker)!

That’s what I did!

A few weeks back I found fellow Vermonter, Kristen Silverman, a milliner at Silverhill Creative Millinery on Instagram, and messaged her right away and said LET’S COLLABORATE!

All of her hats are HANDMADE, and they are just WOW!

I wasn’t sure which hat would work on me, so I asked Kristen, and she suggested a fedora and a cloche.

I could see the cloche, but a fedora?? Am I cool enough to wear a fedora?

I was leery.

The cloche was LOVE at first site. The color was perfect for my skin, the whimsical twirls suited my character and personality, and the style was indeed flattering.



And now, the fedora.

As soon as I put it on, I decided NOPE and took it right off. Then I tried it on again. Still nope. I took it off. I tried it again. Left it on. Walked around the house for a little while. Put on some BOLD lipstick. Added earrings. Then sequins. Checked myself in the mirror about one bajillion times. And then it hit me… I LOVE THIS HAT!



The fedora connected me to that part of myself that is LIVING AT THE EDGE OF HER THINKING.

The risk taker. The rule bender. The fierce lover.

The cloche connected me to my fun and whimsy, which is easy and comfortable for me. Like tinted chapstick.

The fedora, on the other hand, was like that first time I wore red lipstick. At first I panicked and said NO WAY, and then after a few tries, I fell IN LOVE!

I AM one of those gals that can wear a fedora!!

What kind of hat-gal are YOU?? Tell me in the comments about YOUR favorite hat style!

Let’s hop on this hat-wagon together!

With Love & Gratitude,
xo Stasia

PS. BOTH of these one-of-a-kind hats are FOR SALE on Kristen’s Etsy site HERE. And doo-do-dooo, she’s offered to give YOU 15% off any HANDMADE hat of your choosing using the code HATSTYLE.

15 Comments on How to Wear a Hat.

  1. Kristin
    January 24, 2016 at 7:17 pm (1 year ago)

    This post made me smile from ear to ear. Thank you for featuring my hats so beautifully!

    And I love the bit about not wanting to miss Carson and Mrs. Hughes’ wedding. Haha! So true!

    • Stasia
      January 24, 2016 at 7:26 pm (1 year ago)

      So glad you liked the post, Kristin! It was a pleasure wearing your hats!! xo Stasia

  2. Tracy
    January 25, 2016 at 8:20 am (1 year ago)

    Beautiful hats. Love the cloche. And it’s funny that you kept putting on and taking off the fedora. It’s awesome. I can see how you would need to be brave to wear it’s a different, funky look that you don’t see every day.

    • Stasia
      January 25, 2016 at 12:23 pm (1 year ago)

      Totally! You don’t see lots of fedora’s here in rural Vermont. :) I was just “borrowing” these hats, but girl… I’m on the lookout for a fedora of my own, that’s for sure! xo Stasia

  3. Gigi
    January 25, 2016 at 8:48 am (1 year ago)

    You look amazing! I love the fedora on you – absolutely you can wear that one! I like it better than the cloche. I always love hats but cannot wear them because I feel like I can’t pull it off with my dumb old glasses on. I HATE MY GLASSES! It always seems like I just have way too much stuff on my head and it makes me crazy. Any tips for us glasses wearers? Or should I just keep away from hats like I usually do?

    • Stasia
      January 25, 2016 at 12:21 pm (1 year ago)

      Hi Gigi! First of all, I’m a firm believer that glasses are one of the coolest accessories out there! Oh, I’ve pined for glasses for YEARS, but heck if my vision isn’t PERFECT. So, my first question to you is this… do you LOVE your glasses? Are you wearing them as a favorite accessory, or simply as a visionary-tool? Because I TOTALLY believe that you can wear glasses AND a hat and look absolutely FAB! Just google “how to wear hats and glasses” and see what comes up! Or try Pinterest. You’ll need to find the RIGHT hat to go with your glasses… kind of like I need to find the RIGHT hat to go with my short hair. There are lots of hat styles that I love… but they just don’t work with short. I should do a post of me in some NO WAY hats :) So that’s my advice, mama. Make sure you LOVE your glasses and then start trying on every single hat you see!! And when you find THAT hat, please let me know! xo

    • Kristin
      February 2, 2016 at 10:32 pm (1 year ago)

      Hi Gigi,
      I’m the milliner in the blog post — and I wear glasses! (I wear both glasses and hats every day.) When I had glasses with barely-there frames, it was definitely “easier” to wear hats. Now I have thick, purple plastic frames, and I find they go better with fedoras than with cloches.

      The trick is to balance where the focus is, so they’re not competing for attention. If you have colorful frames, go for a neutral colored hat. If you have neutral colored frames, go for a colorful hat. And above all, just start wearing a hat. Once you get used to it, it doesn’t feel as weird or conspicuous.

      Here’s a picture I posted to Instagram the other day, where I’m wearing glasses and a hat.

  4. Melinda
    January 25, 2016 at 12:46 pm (1 year ago)

    I LOVE hats and have bunches of them. Newsboy style for the weekend (no shampoo hair), baseball style for workouts in the sunshine, big brimmed sunhat for the beach, and many different winter hats for function and sassiness. I agree that we can all wear hats if we want and dang when they work we look AMAZING and unique b/c so many people are too afraid.

    • Stasia
      February 2, 2016 at 9:45 am (1 year ago)

      Amen to that, Melinda!! NOT many folks where hats, except for functionality, so when you do wear one – it gets noticed! I love that you are such a hat wearer – of so many styles and varieties! I love the newsboy style too… I have one from Goorin Bros that I wear on not-doing-my-hair-days!! Keep wearing, girl! xoxo Stasia

  5. Crystal
    January 25, 2016 at 4:25 pm (1 year ago)

    I own exactly three hats. One is a vintage wool fedora/ish hat. One is a a custom, one is a kind hand made knit hat, thats not squite a snood, not quite a beret and my third is my Imperial Officer hat ( Star Wars.) The one I wear most often is actually that Officer’s hat, because I wear it with a costume, for he 501st Legion, while we rase money for charity.

    • Stasia
      February 2, 2016 at 9:47 am (1 year ago)

      Yay for hats, Crystal!! And way to have the courage to WEAR THEM! :) STASIA

  6. Kristin Bigouette
    January 27, 2016 at 9:02 am (1 year ago)

    Is there anything you can’t do?! You’re adorable in everything! With my short hair I’m not a huge fan of hats. But you pull it off great! Ill have to take your advise and start trying them all on! I’m more of a bandana wearin girl! Pin up style.

    • Stasia
      February 2, 2016 at 9:42 am (1 year ago)

      Ha!! Oh girl, there are LOTS of hats I can’t wear… I just don’t post pictures of them because they don’t ever make it into my house! :) So yes, just start trying on every hat you see until you find that gem – and then BUY it!! xo Stasia

  7. Megan
    August 18, 2016 at 2:59 am (8 months ago)

    I’m happy on two counts: first, I found Thrift Me Pretty, & then I saw this post & checked out Kristin’s hats & bought a great navy fedora! Thanks much, Stasia & Kristin!

    • Stasia
      August 24, 2016 at 4:41 pm (8 months ago)

      Oh my gosh that’s so fantastic!! Any gal that can rock a fedora is my kinda gal!! So glad you’ve found me over here in this neck of cyperspace, Megan! Make sure you get on the email list (if you haven’t already) so you don’t miss a thing! xo Stasia


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