Hat Guide: Buying The Best Hat For You

I have wearing my new hat by Janessa Leone in a lot of post lately and have been getting TONS of questions and comments about it. I am also super into hats, so I figured we all needed a post about it. I did go through a major search before I found the one I bought and through that process learned a lot about sizing and styles that I liked.

Hat 1Couple things to address:

1. If you are sitting there reading this right now thinking, I love hats, but I just can’t pull them off. Stop. Yes, you can. Everyone can. It’s just about finding the right one that suits you. I went through 4 orders of purchasing and returning before I found this hat. Do not be discouraged, just keep trying. You will find the perfect hat for you.

2. Hats are your best accessory. The last few weeks have been rough for me (in a totally superficial way), because my grey hairs were EXTREMELY overgrown. I do have an amazing grey coverage product that I use, find that here, BUT they were so overgrown that I got tired of even using that. The reason so many of my post featured my new hat was because I do love it, but also because I’m lazy and needed help covering my grey roots until my hair appointment. A cute hat can make an outfit and also cover overgrown roots. Just saying.

hat 23. Sizing. Make sure to read about the brands sizing suggestions. Get out your tape measure and actually measure where they tell you to. In the brand I bought, I wear a large. I do not have a big head, so this was shocking to me and actually, I am more a medium and a half. So, I ordered the large and then I ordered this hat sizing tape to fill in the gaps and give me the perfect fit.  Find that here.

4. Prices. I have been in the market for more of an investment hat. I knew I would wear it a ton and I wanted it to last. There are all different ranges of hat pricing as you will see below. Decide what kind of hat-wearing-girl you are and choose your price point accordingly. If you think you will wear it a ton, you probably won’t feel so bad paying a little more for your hat. If it’s a once or twice a season kind of thing, aim for the lower price point to still feel like it was a good purchase.

Now with all of that out of the way, here are my favorite hats out there right now. So many cute shapes and sizes. Email me or comment below if you have any questions!

Shop my outfit and hat here:

hat 3


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  1. Sizing really is a big thing to consider when choosing hats and it is great that the article agrees. As is pointed out, you definitely want to measure in advance before choosing a hat. After all, you never want a hat that’s too tight unless it is a cap designed to specifically hug the skull.

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