Hey y’all! Several commenters on my last post asked if I had any tips for how to make hats flattering. Well, I did a post on this very topic nearly exactly 5 years ago here on Fresh Modesty, so I’ve decided to re-post it below in all of it’s 17-year-old-me glory. 🙂 I have more tips I can share in the future about specific styles, but these are the basic ones. Enjoy! 
I love hats. Totally, totally love them. But I’ve heard and seen that some people have a hard time getting a hat to look good on them. 😀 I’ve only met one person in my life who truly does not look good in any of my hats. And that’s my mom. 😛 I’m here to share some hat-wearing tips with y’all today. I think 99.9% of people look good in hats… if they know how to wear em. 🙂
These pictures were taken back in early November [2009] between my brother being born and our family moving, hence the cluttered background. Thank goodness for SLR’s! 😀
This is Rachel. You’ve met her before. She took all these pictures. 🙂
[yes, THE Rachel Clarke. Here is her website.]
How NOT to wear a beret. Mushroom looks are bad. Instead, lean it off to one side or the other and flop it a bit.
Like this.
Another tip is not to have your hair pouffy or wider at the bottom than your hat is on top. Or, if it is pouffyish, add interest to it by curling bits here and there or all out curls or straighten it. Or just use hairspray to make it peicer. Whichever you choose, don’t let your hair look like a solid mass of brown or blonde. 🙂
This hat isn’t terribly flattering on me. See how my hair looks wider than the hat? That’s part of the problem. The other problem is that the crown of the hat is slouched backwards. When I wear this hat, I push the crown forwards over the brim a bit so it doesn’t look too small.
Pretty, plain angora hat. With the furryness of it, I have to make sure that my hair is slimming, or else it looks frumpy. 🙂
Adding a sleek black ribbon on the side or front works as well.
Here’s another unflattering one. These hats look good on my sisters, but not on me. 🙂 Again, it’s the hair wider than the crown.
This is slightly better, but isn’t terribly cute. The bright green ribbon brings attention to itself, giving more “weight” to the small black hat.
If your hair just won’t cooperate, try wrangling it into braids.
And its slimming sometimes. 🙂 Leaving random short curls out of your braids can be really cute.

I got these pieces of hair to be shorter by pulling the front of my hair into a pouf and then curling it. It also kept the annoying hair in front out of my face. 😀
Wasn’t my clothing-storage system elaborate? 😛
This style is really cute for ice skating for winter or with a felt beret for fall.
 Remember this hat wasn’t so flattering? Well, with braids, it is!
 So is this one! Amazing, isn’t it? 😉
 Now this hat is just like the pink angora one, except the fuzzies are a little shorter. We pinned up one side of it to give it more interest. Facing forward it reminds me of Paddington… (would be cute with rainboots and bright yellow rain coat ;))
 But on the side it’s much classier. Unless you make that face. 😛
We usually wear it on the side.
 Lest you think these hats only work on me, here is my sister Emma. Her hair is on the pouffy side.
But its still cute. 🙂 braids may help. She actually usually braids her hair when she wears hats.
 Again, no mushrooms, please.

We curled parts of her hair to give more definition and it helped. 🙂
Don’t you love hats? Was this helpful?
Hehe, funny how much can change in half a decade. 

19 thoughts on “Archives // How To Wear Hats”

  1. your sister looks just like you except with brown hair! do they all look like you? i don't wear hats very much, but maybe i will put a little more effort towards styling one next time!

  2. I have always loved hats, but I have had a lot of trouble actually feeling comfortable and put together in them. Your tips were really helpful to me. And also, I love the braids and hat look! I'll definitely be giving that a go!

  3. I like that you shared a post from "way back when"! 🙂 There's some great advice in here. I wish I owned more hats than I did, and if I do get more soon, I may look this post up again just to make sure I've got everything right!

    dance a real

  4. Cute post, Olivia! Thanks for sharing (or rather, re-sharing). I especially love the beret and the ribbon added to the "plain angora" hat. So classy!

    My problem with hats is that they're usually made for people without bangs. My forehead is shaped in such a way that I HAVE to have bangs in order to look nice, otherwise I'd grow them out and save myself a lot of frustration. Any tips for fringe-friendly hat-wearing?

    God bless,
    ~"Tom Wild Rose"~

    1. I have bangs too. I would say to wear beanies, cowboy hats, fedoras, and maybe try a baseball cap. If you want to wear a beret, then instead of just tipping it to the side, slide it back a little more on your head, and you could pin it down if necessary. Or you could just try on as many hats as you like and see which ones flatter you most. (that's what I did)=)

  5. I have such a problem with hats (due to my Big Head Kid syndrome :P) It's kinda scary to think I'll be the same age you were in this post, this fall!

    I like the way you do your hats, though, and it's giving me some ideas!


  6. I wish I could figure out how to wear my slouch beanie with my super long hair. My hair is knee length and even braided it pushes the hat up off my head.

  7. I have actually been thinking about wearing dress hats, especially in the winter. I went to a graveside funeral last weekend and it was miserable without a hat. All I had were my 'around the house' hats that I wear when doing farm work. I'll have to keep this in mind when I start looking for a hat.

  8. Ahhhh! I feel so old! I remember when you first posted this, lol! But I starting LOVING hats in the last 2 years, so this is great to reread. I love how you put a black ribbon on that pink hat! I think I'll try something like that with my plain black one.

  9. I love hats so I was very excited to see this post. I've never had a problem with finding hats that look nice on me but my sisters each have to be careful about which hats they wear. We did a hat day and they tried on lots and lots of various hats till they found their styles. It was really fun.

  10. I just happened to slip on your blog, and I absolutely love it. Keep blogging because there is no blog like yours. 🙂 I especially love your blog because I too want to make one that's about modest fashion and I have been wanting to be a fashion designer and I'm making a book and your giving me great ideas I never could think of! 🙂

  11. Do you have any "derby" hats? How can I incorporate those into my fashion without making it too loud and out there?

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