The Best Hat for Your Face Shape

As you guys might remember from this post here, I’m totally loving hats this season. Any chance I have, it seems like I’m reaching for a hat to complete my look!  But, the real question remains… what type of hat should you wear for your face shape? Though I strongly believe that if you love something and it makes you feel good you should wear it, I took a little step back to my styling days to break down the best hat for your face shape!

Round Faces, try a structured hat: Janessa Leone (Similar Here)

This structured beret from Janessa Leone (check out a similar hat here!) is perfect if you have a rounder face. Since it’s more structured, it really helps to visually add angles and stronger lines! If you’re not the biggest fan of the beret shape, a hat like this one or this one would also do the trick!

Angular Faces, try a beret: Janessa Leone

If you guys have noticed from this blog post here and all over my InstagramI just can’t get enough of berets this season! My face is very angular, so wearing a more relaxed kind of hat helps to soften up my face. This one from Janessa Leone is super soft, and I love the neutral camel color. Who would have guessed berets would be so in?

Oval Faces try a Baker Boy: Isabel Marant

I think I’ve lost count of how many times I’ve worn this hat! Not only is it super chic, but it’s also really affordable (shop it here!) as far as designer hats go! The baker boy hat is pretty universal, but I think it looks really great on longer and oval shaped faces. It’s got a good balance slouchy and structured!

Bigger Foreheads, try a baseball cap: Vintage (Similar Here)

I’ve talked about this before, but I was super insecure about my big forehead when I was younger. Though I’ve learned to embrace it, I noticed that I love the way baseball caps look on me because of it! I actually got this hat from a vintage store in Tokyo, but check out a similar one here and some more that I love in the widget above!

So which hat is best for you? And remember, if you love something and you feel good in it: own it and wear it! Leave a comment down below and let me know if there’s any content you want to see on the blog this season!



  • Dawn G says:

    Valid pointers here! My face is rounder now and no wonder that I find structured, fedora hats to be more flattering. When my face was slimmer, I wore wool berets with my cocoon winter coat. XOXO

  • Jade says:

    I love your styling! All these hats are so cute!!

  • tanja says:

    i love this hats! great shape
    xo tanja

  • the berets are so cute!

    xoxo Christine Jessica

  • chichi says:

    this is such a helpful post!

  • Great ideas! A Baker Boy is m favourite and works better with my face shape!
    New post: 7 Things You Never Knew You Needed in Your Beauty Bag

  • Shloka says:

    This is a really clever way of showing us which hat might suit! Thank you so much for sharing – I love all the styles!


  • Simply Sory says:

    No a todo el mundo le sientan también bien tantos tipos de gorros diferentes. Me encantan la boina.

    Te dejo mi nuevo post, es tiempo de medias

  • Elizabeth says:

    Loving all of these great hat options! 🙂 The right fit for your face shape really makes all of the difference, so thank you so much for sharing this great guide, Chriselle!

    XO, Elizabeth

  • Vivian says:

    I needed this post! Thanks so much for the tips Chriselle, off to browse structured hats now!

    Vivian | LIVE IN LOVE
    IG | @viviyunn_


  • I look terrible in hats, but would love to wear a beret! Theyre just so cute!

    XOXO //
    SINCERELY OPHELIA | NYC Petite Fashion Blogger

  • Jennifer says:

    This post was so helpful! I love wearing hats, especially during the colder days.

  • Meghan Burns says:

    Great tips. Love this. So fun. A lot of times I wear hats and then take them off in the car before I get anywhere. I don’t know why but I chicken out with hats. This post made me want to wear hats more.
    xo, Meghan |

  • Magda says:

    Great post, I love baker boy hats and berets but I don’t look gratvin baseball caps! xo

  • Annabelle says:

    You really suit hats! I’ve got a round face so I’ll definitely try some more structured hats, although I really wanna get some baseball hats too but I’m not sure they suit me…

    Belle in Black and White

  • Jandrew says:

    Darling you look great in hats in general! ButbI really love The baker boy
    Dress The Part

  • Tshering Peldon says:

    You look fabulous in all the hats. I can’t pull of the newsboy hat. But still I wear it like it’s no one business.. hehe

    Have a great day ❤️

  • Keren says:

    Love how the beret looks on you! Gorgeous!
    xx Keren

  • Oroma says:

    Love this, I need more hats in my wardrobe for sure!


  • Marianne says:

    Loved this! Inspired to start wearing my winter accessories again 🙂

  • Marta says:

    I’ve always been a bit scared to try out new things when it comes to accessories, especially hats. Only recently I’ve ventured out and gotten a floppy hat but this year I really want to try and get something more. Thank you for the tips!

  • Ray says:

    Oh I’m such a hats girls. Extra life.

  • ANGELEBABY says:

    such good tips as always! def need to try out more structured hats for my moon face haha

  • […] Though I strongly believe that if you love something and it makes you feel good you should wear it, I took a little step back to my styling days to break down the best hat for your face shape! from The Chriselle Factor […]

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