November 8, 2011

Warm and Stylish Winter Hats For Moms…a Roundup!

PC301494Hats are, hand's down, one of the easiest ways to add style to any outfit.  This pic is of my adorable sister-in-law (mom of three boys, therefore a super-star) rocking a totally adorable hat that I'm STILL coveting, almost a full year later.

So when we received the following question from reader Michelle, I was only too thrilled to hunt for hats: 

Love, love love your blog! Discovered it last week and have been reading all of the articles for this month. Funny, fashionable and relevant! My favorite ones so far are the "How Sleep Trained Us" and "Your Pre-baby Body Called, It's Not Coming Back". Hilarious!

My question is about what kind of winter hat to wear. I feel like I have a big head! Living in Kentucky, it's not tundra cold, but it does get chilly during the winter. I would like to find a cute, warm hat to throw on for days when I don't have a chance to do my hair (which is always with two boys under age 3)! Thanks!


Yeah, I feel Michelle's pain.  I, too, have a big head.  However, hats are having a moment right now, so choices abound, which helps when fit is an issue. And don't be shy about checking the men's department – I'm wearing my husband's hat here.

Warm Hats

For an update on the standard wool beanie, look for fun details like a cool breton stripe, a bit of slouch, faux-fur, an over-sized pom, or a hand-knit look. 

With the exception of the cashmere navy & green striped hat below, all others are under $35. 

Warm and Stylish Winter Hats


Cafe View Knit Beanie
$13 -


Oasis knit beret
$25 -


Earflap hat
$30 -


ASOS slouchy beanie
$14 -


GAP cable knit hat
$30 -


Madewell slouch hat
$32 -


Lands End wool hat


Cooperative hat
$24 -


Knit hat
$35 -




Hats With Serious Style

If you are planning to rely on hats for more than just playing in the snow, consider choosing one with a little more style.  For some general examples of incorporating hats into your basic mom-uniform, see our article, Summer Hat Picks You Can Wear Now Into Fall.

I love the brimmed Engineer hats below (and those of you with a girly style should check out the polka-dotted one from Modcloth, below)….but the wool fedora (bottom left corner) has to be my new favorite.  SO flippin' cool. 

Really, just about any hat style works – cloche hats are great, floppy hats, wide-brim fedoras, boaters, etc.  

The bottom line?  Yay, hats.  

Stylish Hats - Winter


$24 -


$38 -



Tarnish fedora hat
$38 -



Jessica Simpson cap hat
$28 -


Deena Ozzy felt hat
$34 -


K2 hat
$25 -


Madewell tartan hat
$59 -




Wow….Just Wow.

I couldn't NOT include these for some reason.  And I don't have much to say here, except that if you CAN pull off one of these babies, you are my hero.  If I saw a mom cruising around with her kiddo wearing, say, the faux-fur bunny-ear hat?  I'd have to befriend her immediately.  Cause I'm pretty sure she'd rock.

(I'm only including faux-fur pieces.  I'm too much of an animal lover to endorse real fur.)

If You Can Pull These Off You'll Be My Hero


Fake fur hat
$54 -


ASOS fake fur hat
$45 -


Gap hat
$35 -


Brim hat
$34 -



Asos Faux Fur Earmuffs
$17 -




Wait!  Didn't I predict the rise of statement hat last year?  Snort.  Ah, yes.  You didn't realize that you are reading the words of a fashion visionary, did'cha?  Watch out, Mammas.  We'll all be in faux-fur bunny-eared hoods before you know it.



  • Erica
    November 9, 2011

    I like the idea of adding style via hat…but don’t think they’ll work well with my super-short mom hairstyle. 🙁

  • Tysie
    November 9, 2011

    Not gonna lie – I want EARS!!!

  • Jess Jones
    November 9, 2011

    I have far too many hats… A fashion vice for me for sure. One of my fav brands I highly reccommend: Coal.

  • EmmaKate
    November 9, 2011

    I love the cute Oasis Knit Beret! but i have A LOT of curly hair, and often the result is a bit like a cocker spaniel (which i also have 🙂 so aside from taking the hour and a half to make straight hair, i will just have to admire all the lovely hats!

  • Jen
    November 9, 2011

    Check out Piper & Paisley on etsy. Super-cute hats. I bought one two years ago, and it’s held up great and is a playground staple.

  • S
    November 9, 2011

    Erica — Hmmm….it seems like short hair could work…I’m going to try and find some examples….
    Tysie – SO glad I’m not alone in this!! LOL But it is a bit crazy. 🙂
    Jess – Thanks for the link – awesome!
    EmmaKate – OMG I love curls. You lucky duck.
    Jen – Oooooo….soooo cute…. Thanks!!!!

  • Megan B
    November 10, 2011

    Erica, when I had super short hair I found that I needed to wear a really feminine hat or one with a brim. If you wear a beanie style you can easily be called “Sir” (trust me, it happened to my sister!). The ones in the middle section above should work!

  • skippysays
    November 10, 2011

    Love your striped hat picks for the warm cosy ones! And of course all of the “wow… just wow” ones too 🙂

  • Crunchy Con Mom
    November 12, 2011

    I have a hat almost exactly Luke the white fur ASOS one in your wow section that I totally love. I try to pay extra attention to the rest of my outfit so it’s obvious I’m being intentionally quirky and I’m not just fashion inept.
    EmmaKate-back in college when I had time to curl my hair, I found that the curlier I could get my hair, the cuter the engineer/pageboy hats looked! I think the brims help balance big hair more than other types of hats.

Leave a Reply