Outfits to Wear With A Beanie

I remember having a few beanies, or skullcaps, around when I was a kid. I was utterly embarrassed to have to wear one. I didn’t find them to be very stylish and they were solely for keeping warm while working outside on the farm.  We had a few that had our high school’s name and mascot on them in our school colors complete with an utterly embarrassing pom pom.  I’d rather have been cold than to have been caught in one.

Fast forward to my adult years. 

I’ve managed to find a few ways to incorporate them into my wardrobe for both style and function. It’s taken some trial and error, but I’ve learned a few tricks about wearing a beanie, and I’ve got a few outfits to wear with beanies to share with you.

Before we get to the outfits, let’s talk about beanies.

Not all beanies are alike.

A beanie is a flat, close-fitting soft knit hat without a brim. Like many fashion items we have today, it started out in history as a functional item worn to keep warm. It was favored by workers who didn’t want a brim in the way.

Looking your best in outfits with a beanie involves choosing the best one for your face shape, the same as looking good in any other hat.

If you have a round face, choose a beanie with some height. If you have a long face, choose a shorter beanie.

It’s all about balance. If you don’t want to make your face look fuller or chubby, add some height with your beanie or don’t wear it pulled all the way down. If you don’t want to exaggerate a long, thin face, wear a smaller, shorter beanie.

While the design and premise are the same, there are a few variations in types of beanies.

Some fit closer to the head than others.

Short/ fishermen beanie

This type has a vert short crown and may not cover your ears. It’s been noted that they were developed because fishermen had a habit of rolling up their beanie caps over their ears so they could hear better.


Ribbed knit fabric is soft and stretchy, with a ribbed texture.

Cable knit

Knitted in a cable pattern


A longer style beanie with extra material that slouches to the back

Pom Pom

A knit, or cable knit beanie with a yarn or faux fur pom pom (a decorative ball) on top


Knit or smooth, with a cuff around the edge. Sometimes it’s tack in place and sometimes it can be unrolled


Less shape and more fitted to the head.

Not only do you need to consider the outfits you wear with beanies, but you need to consider how you wear it on your head.

Four basic ways to wear a beanie

High– If the fabric is sturdy enough, let it sit straight up on your head.

high beanie
Portrait of beautiful smiling model. Woman dressed in warm hipster white sweater and beanie. She posing in the street at sunset in sunglasses

Pulled Down– Pull the beanie all the way down to your eyebrows and frame the face with it.

beanie worn pulled all the way down with chunky cardigan

Slightly slouchy– Fold a little excess to the back

slightly slouchy beanie

Super slouchy– This is a cool way to wear a beanie and is more for style than warmth. You may need a hair pin to hold it in place if you wear it pushed back on your head.

super slouchy beanie

Some people hesitate to wear beanies because they don’t know how to account for other needs and variables and have too many questions about wearing a beanie.

Can you wear a beanie with glasses?

Absolutely! You may have to put your glasses on first and pull the beanie down over the legs or slide the beanie back a little to accommodate glasses, but they can be worn with glasses.

Can you wear a beanie with short hair?

Certainly. I do. I’ve worn beanies with various lengths of hair, but I find wearing a beanie with a pixie cut just as easy, if not easier, to wear than with long hair. Pull some bangs out and let them show.

Can you wear a beanie with curly hair?

Yes. You may have to braid your hair or pull it to a low ponytail to the front to make the beanie fit, or even utilize hair pins to help it stay. A beanie with a silk or satin lining is recommended to keep the beanie from damaging your curls. If you have loose curls, just let then flow out from under the beanie.

Can women over 40 wear a beanie?

A beanie can give you a youthful appearance, but they are not strictly for the young. A woman of any age can wear a beanie if it suits her face shape.

Outfits to Wear with A Beanie

These outfits with a beanie are mostly casual outfits with beanies, but you can certainly wear a beanie on your work commute with polished work wear outfits.

Soft, ribbed knit cuffed or cable knit beanies would be a better choice with your dress coat. Leave the casual slouchy beanies or beanies with logos and designs for the weekend.

The Outfits

Match up a cable knit beanie with a cable knit sweater.

It doesn’t have to be an exact match, but sticking to the same color family will create a striking look.

cable knit sweater

Beanie- similar; sweater- Gap; jeans- Loft; boots- Amazon

If you have a beanie, you probably have a plaid flannel shirt in your wardrobe.

The two make a classic outfits with beanies. Add a mockneck top or turtleneck top under your sweater. Pair it with light wash jeans and finish off with Chelsea boots.

plaid shirt winter outfit

Shirt- Old Navy; option turtleneck- option; jeans- Gap; option boots- Amazon; beanie- Amazon (this one comes with a satin lining)

Beanies pair nicely with plaid, vests, sweaters and boots.

Here I mixed patterns with the top and vest. The faux fur on the pom pom compliments the fur trimmed boots.

winter outfit

Shirt- Amazon; similar; vest- similar; jeans- similar; boots- similar; beanie- similar

A fair isle sweater always says “winter outfit” and a beanie is the perfect compliment. Add a vest for more warmth and interest.

outfits to wear with a beanie fair isle sweater

Sweater- Target/ old option- Old Navy;

You can certainly wear a beanie with a dress. It is especially appropriate with a sweater dress. Try a soft beanie with embellishments and wear it with a slight slouch. It makes a great accessory this way.

embellished beanie with a dress; outfits to wear with a beanie

Dress- Old Navy; boots- Target; scarf- JCrew Factory; option beanie- similar

A shacket makes another great winter beanie outfit. Go neutral with creams and greys.

shacket outfits with a beanie

Shacket- Amazon; body suit- Gap; jeans- Old Navy; Chelsea boots- Mia; beanie- Amazon

Layer up in leggings, tee shirt, chambray and a utility jacket. Finish off the outfit with a slouchy beanie.

(This is my least favorite look for myself because the beanie is the least flattering for my face. Like I said earlier, it took some trial and error to find the best look, but I like the slouchy vibes of the outfit on someone who can pull it off.)

slouchy beanie outfit with utility jacket

Leggings- option; chambray- option; utility jacket- option; beanie- Target

A beanie makes an excellent choice for a winter hat. They help keep you warm and you don’t have to worry about the wind blowing them off like other hats. Use them as a cute accessory to level up your winter outfits.