Hats Every Fashion It Girl Should Own

the must have hats every fashion it girl should own, stack of hats - My Style Vita @mystylevita

Over the years I’ve grown to love my hats. I was always a little nervous to start wearing them. Not sure why, I tend to be pretty confident in my fashion choices. Not that they’re super out there and different, but I just consider myself to be fairly confident. But something about the hat I was a little hesitant to rock at first. Maybe because it was new and not something I ever wore before. But now? Now my hats are my absolute favorite accessory. And there’s a few hats that every fashion it girl should own.

PS last week I also shared how I display my hats in my home. They were taking up a ton of space in my closet and I found a simple solution to a decor problem. Now this is my favorite part of my home.


1. Floppy Brim Fedora

I grabbed this Rag & Bone hat a few years ago at an event (a gift card helped with the steep price tag thankfully) and it’s been such a good buy. I’m a sucker for navy too and it’s just a luxurious looking hat. These are great for fall and winter to keep your head a little warm while also being stylish. I also love the extra wide brim on mine.

$195 Rag & Bone Fedora

2. Braided Sunhat or Straw Panama Hat

These are very similar and in my opinion, pretty interchangeable so they’re being grouped together for today’s list. This hat is slightly different than my favorite (number 5 on today’s list) but just different enough that it needs to be included. A big sun hat is a must for beach days and summer brunches on a patio. I also love a good straw panama hat too. They’re very similar, and it’s just a preference on how wide you want the brim to be. You can go SUPER wide in a big floppy sun hat, or more refined in a panama hat. Either way, one will do in your collection.

Brixton Joanna Straw Hat

3. Baseball Hat

You’ve only seen me wear a baseball hat just once on the blog. This is the one hat trend I have a hard time feeling cute in. I think I’m doing something wrong, but I do love it on other people. If you have any tips on having this look cute on me, let me know! I really want to embrace it for those lazy days I don’t want to do my hair. Also, I need this pink velvet one.

Madewell Corduroy Baseball Hat

4. Knit Beanie

I was never into the knit beanie until I found myself in NYC during Juno a few years ago. The weather shit storm came out of nowhere and I was FREEZING. Luckily, Cathy brought several beanies and I finally learned how great it was to have your head and ears warm while surviving a blizzard. I love a more slouchy fit, but they look terrible on me. 

Slouchy Fleece Beanie

5. Boat Hat

Hands down, my most favorite and most worn hat in my closet (or should I say hat wall) is my boat hat. I’ve worn it non stop to the point where it’s actually starting to fall apart a bit. I’ll be honest, it held up pretty darn well. It’s been to various countries, packed in suitcases and worn for days on end sometimes. 

Eugenia Kim Brigitte Hat

Featured image by JNelly

Leave a Comment


  1. Kate wrote:

    All so good! That corduroy baseball hat is calling my name!

    Posted 8.17.17 Reply
  2. Nataly wrote:

    I love all these hats!

    Posted 8.17.17 Reply
  3. I love baseball hats and the knit beanie! I have a beanie that’s hand made and LOVE it. I don’t have a fedora but I think I might pick one up!

    Posted 8.17.17 Reply
  4. Lauren wrote:

    I’ve always had a love-hate relationship with hats… love them on other people, and hate them on me haha! I think it’s got to be my head shape or something, but if I had to pick, I would definitely go with that cute braided sunhat!


    Posted 8.17.17 Reply
  5. Ashley wrote:

    I wear baseball caps to try to cover up day or two old hair… especially when running errands! Nothing fancy lol!

    Love these hats… I need to get more!

    Posted 8.17.17 Reply
  6. Lily wrote:

    I love, love, love hats! I don’t have any boat hats — but they don’t look very good on me.
    xo, Lily
    Beauty With Lily

    Posted 8.17.17 Reply
  7. Laura Leigh wrote:

    I have them all except for a boater! Which I’ve been dying for. I really need to get on that and find the perfect one. Great post Jess!

    xo Laura Leigh

    Posted 8.17.17 Reply
  8. Ruthie Ridley wrote:

    These has are amazing!! I love every single one!!

    Posted 8.17.17 Reply
  9. Anna English wrote:

    Ah! Love a good boater hat too, there was a ton of cute options this spring/ summer!

    Posted 8.18.17 Reply
  10. Steph wrote:

    Oh my goodness yes! I love hats. I haven’t worn them as much lately as I normally do, but with fall and winter coming up, I am sure that will change.

    @trendyinindy || trendyinindy.com

    Posted 8.18.17 Reply
  11. Morgan wrote:

    I am lacking a boat hat but have been contemplating one of a while now!

    How 2 Wear It [] https://how2wearit.com

    Posted 8.18.17 Reply
  12. Hillary wrote:

    I love this post! I’ve always been a bit hesitant to wear hats, too! I can’t wait to go check out how you organized yours! Thanks, Jess!


    Posted 8.22.17 Reply


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