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How To Style The Beanie

Girl in blue beanie

I happen to live in a climate that in order to survive 3 of the 4 cooler seasons adding a beanie to any style is mandatory. Oh, it was a hate / hate relationship from the beginning. I moved from sunny California and while I was a lover of hats the beanie wasn’t one on that list. My style leaned more along the lines of trying to be fancy Nancy. I mean I did I like sporty spice baseball hats, hats with flowers and brims but my all-time fav was probably the lieutenant hat. In the past 21 years of living in the PNW I have learned to be in love with the beanie. Morning, noon, and night. As much as I probably hate to admit it, the beanie is my boo. I love the beanie. When I think of it, I shouldn’t be too surprised after all the woman that inspired me to be a fancy Nancy was my Grandma Emily. She lived in hats, mostly a knitted turban style lined in something silky but she did because they kept her warm but I tell ya she looked amazing in any hat. Much like me, she was a texture person. She liked softy ones, silky ones, and of course shiny ones. I am no different and especially if they are warm.

Fatu Fashion 3PCS Women Turban Knit Winter Hats Warm Knit Cap Knit Hats for Women Warm Headband Cross Twist Knit Cap Beanies Sleep Chemo Caps for Women (Black/Navy/Khaki)

This one or that one

There are so many cute versions of this little gold mine it’s easy to have a whole drawer dedicated to them. Not me though, I don’t have a drawer. FINE, I’m a liar. Big fat liar but in my defense, they are all very different. Why? Because they all have different styles and different vibes about them. There are plaid ones, and yellow ones and some with a rose, there are bright ones and dark ones I mean some even have sayings on them. Nevertheless, they all have a time and place.

And there are a million of them.

zowya Tie Dye Cuffed Beanie with Excellent Touch for Women Men 1 Hat Skin-Friendly Skull Cap Winter Stretchable Knit Hat Colorful Warm Fashion Grey

Don’t be afraid

I hated the fact that when I got a beanie, I wouldn’t wear it until it was broken in. What a conundrum that was. You know that traditional ribbed no frills beanie. What an annoyance that was. So finally, I learned to put it on and start messing around with it. I will stretch the little erect (that is the only word that clearly describes it…helllllo) part on the top of your head and then scrunch it down into place. It’s an ordeal and I wear it around the house for a bit until it’s nice and worn in. Once I figured that out don’t think I didn’t bust out my old ones and do the same.

Dickies Men's Standard Acrylic Cuffed Beanie Hat, White, One Size

Handful of ways

Now that it’s not a straight off the assembly line shape, test it out.

You can wear it in all it’s beautiful structure. This isn’t the most exciting for me, it looks as though you’re always getting ready to ask a question but can’t quite get the words out. I’m weird, I know.

In a classic beanie style, you’ll find me at the one roll every time unless the style doesn’t permit but usually that’s where I’m at. I prefer it with a little slouch at the top with it hitting right at the back of my crown, over the tops of my ears and just sitting right at where that that damn wrinkle just lays on my forehead.

If that’s a little basic for ya and you’re just too cool for that then do the double roll. Nothing wrong with liking it a little high and tight. This look is really polished and a true statement maker.


SATINIOR Trawler Beanie Watch Hat Roll-up Edge Skullcap Fisherman Beanie for Men Women (Black)

Sometimes I’m in the mood for a little beret vibe probably since I have never been able to master that look. I will wear it a little back along my hairline and have some fringe pieces doing a little peek a boo. It’s especially fun if you have a color combo going or is that just something that makes me happy?

You could also live in the moment and just wear it as far back as you can. To me that seems a little risky and you’ll spend most of your time making sure it’s not falling off rather than enjoying your time. Long are those days of wearing high maintenance anything.


You don’t style it you wear it.

Since I clearly have opinions, I think it’s important to talk about how you style with a beanie.

Namaste in this beanie

Who doesn’t love a good yoga pant, sneakers, and a cozy hoodie? I do, but without the hoodie lol it’s too much around my little neck, but I realize that’s my issue. Anyway, we all know that works. It’s cute we all got the memo but let’s make it our own. I like to get out of the basic rut, and I love to pair it with a poncho and some mukluks and more specifically Manitoba Mukluks.

Manitobah Mukluks Women's Mid Gatherer Mukluk, Tobacco, 6 M US

I am all over the board with my fashion picks. Some days you can find me in all black in my best Emo mood or I am Iris Apfel? We all know either, I’m just me. But you know her, right? That fabulous woman who describes her style as “More is more & less is a bore”. I’m with her, well at least on the days I’m not in all black. It’s just good to switch it up for something just as suiting but with a little something something.

My friends, the beanie is not just for a chilly afternoon. It’s super cute for those dress days too. This might fit into my all-black days more often than not but a little black dress with tights and boots along with a pretty little hat adorning your head. It’s like a little soft crown to frame your beautiful face. You can still do your hair, airdried beachy waves, perfectly coifed straight hair, or big and bouncy curls believe it or not it looks good. If you want to keep it all monochromatic sure that works too but don’t be afraid of a little color pop either. Beanies are fun. My suggestion is that if you’re going to incorporate it into a dressier look here, you’ll probably want to avoid the pom pom or a really bulky knit. I mean you know what you’re going for more than anyone, but it could really make it look confusing if it’s too casual. Maybe opt in for a faux fur pom and you know me I’m always going shout out the floral. Trust me, I love the pom pom it saved my life once so I’ve got nothing against it.

Jeans and beanies oh my!

No denying jeans go with literally everything and these little gems are no different. You know what to do here.

Leather pleather

Hands down the coolest of them all is the leather and beanie combo. Pleather or leather whatever your pref is, it’s rad. Pants, jackets, little skirts it’s all rad.

There is more than one beanie

Take the time and try out different types of beanies something that you wouldn’t normally go for. Buy the one you like and wish you could pull off but afraid your man won’t like it. Newsflash he’s not wearing it and if he makes you feel bad about it, ditch him. I bet you feel a little more like you and no I’m not still taking about that dude but hey if the shoe fits… Buy the one you secretly like and wear it. Wear at home and get used to it and then watch what happens. New favorite beanie!!


NEFF womens Cupcake Beanie Hat, Vanilla, One Size US

Are you awake?

The point is find something in your outfit that’s a little element of surprise every day even if it’s as simple and changing the way you work your beanie look. For me it makes me feel like there is still something alive in there even when the days become weeks and then months and then years. So, if you find yourself caught in the automatic pilot mode start trying on beanies with all your outfits. Do it every day and I bet you find a new way to wear it that makes you smile.