How to Make Silly Winter Hats Look Stylish

There are a few things my husband is critical about when it comes to my wardrobe. But he strongly dislikes my taste in socks and hats. Yes, I still wear toe socks and funny little winter hats. I am warm and I could care less about how much he scrunches his nose at me.

He’s not alone though. A lot of people aren’t fond of hats but I, for one, have always loved them. It is cold in Chicago where we live and my mother always taught me that looking cold just means that you’re looking foolish. I got to meet up with a new friend, Soraya, who blogs at Chic Flavours, this morning for coffee and we were both hat ready for the freezing temperatures that are about to hit this city.

I thought that I’d share how we’ve managed to make silly winter hats look stylish and include a few options for you to try at home! Don’t be scared! Embrace the hat!

  • Silly Style 1 of 14
    PicMonkey Collage

    Find out how to make silly hats look stylish this winter. 

  • The Fur Trapper 2 of 14
    fur hat 1

    The fur trapper hat is an option that a lot of people find to be a bit silly, but I love it! Soraya has an all-black one that can be worn with just about anything. 

  • Fur Vest 3 of 14
    fur hat2

    She wore her trapper hat with a very classic ensemble a white button up, black pants, and black booties. She added to the fun by putting on a fur vest in another tone, making the look perfect for winter. 

  • The Perfect Fur 4 of 14
    fur hat

    If you loved Soraya's look, you have to try it yourself with this warm little number. 

    Available at Express, $49

  • Purple Pom Pom 5 of 14
    purple hat

    Soraya also tried a purple pom pom with the same fur vest and both looks worked so perfectly. 

  • The Perfect Knit 6 of 14
    purplepom hat

    This one would be great to add a bit of color to any winter wardrobe.

    Available at Old Navy, $8

  • The Fur Pom Pom 7 of 14
    pompom hat

    This one isn't purple, but it is the perfect combination of fur and pom pom. A great option if you're still a little concerned about rocking a hat made entirely of fur!

    Available at Old Navy, $10

  • Graphic Pom Pom 8 of 14
    snow hat

    This graphic hat is ready for the inclement weather. I know... there's currently no snow to be seen, but I like it anyway. I paired it with a bold lip and leather bracelet from my girlfriend's vintage collection for a great combination of goofy and fierce. 

  • Fun Graphics 9 of 14
    graphic hat

    Because silly hats can be stylish and they should always make you smile. 

    Available at Old Navy, $12

  • Beige Beanie 10 of 14
    beige hat

    This is another option in addition to the snow hat. Like Soraya, I also was rocking the fur vest and no. it was not planned. Great minds think alike! I've been wanting to try plaid and fur together for some time now, but with this bump all my plaid shirts weren't working. Let me introduce you to my husband's closet. His shirts are starting to fit me now. 

  • Beige Pom Pom 11 of 14
    beige hat1

    I love my beige beanie, but a pom pom adds a little something extra special.

    Available at H&M, $12.95

  • Grey Beanie 12 of 14
    OOTD3

    This is actually my beige beanie, inside out. I wore it a few days ago for a stroll in the forest preserve. I paired it with a vintage jacket, a bold pink scarf, and matching lip. You'd be surprised how far accessories will go!

  • Beanies At NYFW 13 of 14
    beanie hat

    Here I am this past February during New York Fashion Week. I wore a hot fuchsia dress and a beanie the entire time to stay warm (and yes, my favorite fur vest). It was the perfect combination of street meets chic. 

  • Jeweled Beanie 14 of 14
    beaded hat

    This is a stunning winter hat to wear when you're doing your holiday shopping, or maybe I'll wear this one for the next Fashion Week! (Even though I'll be enjoying it from the delivery room this year!) 

    Available at H&M, $34.95

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