Winter Hats for Your Face Shape

winter hats 2014

I never used to be much of a hat girl, but last winter I changed my mind. I now am the proud owner of about 6 or 7 winter/fall hats, and let me tell you- they’ve come in handy during my commute to and from work. In the winter cold, hats not only add warmth to your head and ears, but they also can hide messy hair (I can’t be the only one who gets aggravated at the morning winds messing up my locks, right?)

I’ve found that not all hat styles look great on everyone. Yes, there are those freaks of nature who can pull anything off effortlessly, but I’m not one of them. I have a small head, so I have to stick to styles that work well for that. On the flip side, there’s plenty of styles for those with larger heads as well. The grass is always greener, right? Here are 3 hat styles I’m lovely lately- what about you?

fedora hats

Fedora hats for winter

I know many people associate fedoras with dapper men, but I promise that women can pull them off just as well. Fedoras work best for smaller faces with delicate features. If you’re worried that it’ll look too boyish on you, try a pretty color or a ribbon to add a touch of femininity to the look.

womens fedoras

Tarnish Rib Knit Fedora  |  Eric Javits ‘Kim’ Wool Rain Fedora   |  Nordstrom Wool Felt Trilby Hat  |  Topshop ‘New Clean Edge’ Wool Fedora


beanie hats

Beanies for winter

Beanies or knit berets (whichever you prefer to call them- I’ve seen both) are my go-to in the winter. They cover my ears and head but still let some hair show through so I don’t look like a 12-year-old boy. This versatile option works well on all face shapes and sizes- just adjust it to your liking on your hairline and forehead.

womens beanies

 Echo ‘Seasonless’ Slouchy Knit Cap  |  Topshop Embellished Ribbed Beanie  |  Leith Chunky Knit Slouch Hat   |  Zella Knit Hat


wide brim hats

Wide-brim hats for winter

Ah- the wide brim hats. These look amazing on models and celebrities, yet I find them extremely hard to pull off as an average girl. The round and oversized brims of these hats work best on those with thinner faces (think angular faces and a strong jaw), since the roundness might overwhelm an already-round face.

womens wide brim hats

Nordstrom Felt Hat  |  Eric Javits ‘Alixe’ Cloche   |  Collection XIIX Floppy Wool Felt Hat   |  BCBGeneration Laser Cut Floppy Hat


  1. I never wear hats, though I often hear that it looks good on me. I just find it hard to pick the right one 😛 Especially after you sharing off all those lovely hats in your post! Doesn’t make it easier for me, haha. 🙂

  2. The only hat I wear is my Giants baseball “cap” on lazy days in the fall. Hats don’t work for me. I can do the wide brim thing in the summer, but that’s about it.

  3. Excellent guide, doll! I’ve lamented over and over that NO ONE seems to wear hats (outside of baseball caps) here in KC, and I’m desperate to change this. 🙂

    I love a wide-brim hat; super glam!

  4. I’ve been wearing a lot of beanies this fall and winter and love them! I also bought a really cheap wide-brimmed hat at H&M, and I think it’s adorable, but still haven’t gotten up the guts to wear it out anywhere. I think my face my be too round anyways.

  5. I’ve always thought that hats look terrible on me because my face is really so big, but I’ve been obsessed with finding one that looks right this season… they’re just so cute and outfit-completing!

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