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 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.
How to Choose a Beanie That Flatters You
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.
Types of Beanies
While the design and premise are the same, there are a few variations in the types of beanies.
Some fit closer to the head than others.
Short/ fishermen beanie
This type has a very 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
Ribbed knit fabric is soft and stretchy, with a ribbed texture.
Cable knit
Knitted in a cable pattern
Slouchy
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
Cuffed
Knit or smooth, with a cuff around the edge. Sometimes it’s tack in place and sometimes it can be unrolled
Soft
Less shape and more fitted to the head.
Four basic ways to wear a beanie
Not only do you need to consider the outfits you wear with beanies, but you need to consider how you wear them on your head.
High–
If the fabric is sturdy enough, let it sit straight up on your head.
Pulled Down–
Pull the beanie all the way down to your eyebrows and frame the face with it.
Slightly slouchy–
Fold a little excess to the back
Super slouchy–
This is a cool way to wear a beanie and is more for style than warmth. You may need a hairpin to hold it in place if you wear it pushed back on your head.
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.
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.
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.
Yes. You may have to braid your hair or pull it into 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 them flow out from under the 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.
If you have a beanie, you probably have a plaid flannel shirt in your wardrobe.
The two make a classic outfit with beanies. Add a mock neck top or turtleneck top under your sweater. Pair it with light-wash jeans and finish off with Chelsea boots.
Beanies pair nicely with plaid, vests, sweaters, and boots.
Here I mixed patterns with the top and vest. The faux fur on the pom compliments the fur-trimmed boots.
A fair isle sweater always says “winter outfit” and a beanie is the perfect compliment.
Add a vest for more warmth and interest.
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.
A shacket makes another great winter beanie outfit.
Go neutral with creams and greys.
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.)
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.
