How To Wear A Beanie: The Ultimate Style Guide

While the beanie may be a wardrobe staple for the cool kids, it can also be a bit of a style challenge. But before you throw in the towel, or in this case, a beanie, know that there are plenty of ways to wear this winter essential. Beanies are perfect for cold weather or a bad hair day!

The beanie is undeniably an important part of the modern fashion landscape, especially in winter. From music festivals to ski slopes, beanies have been spotted on everyone from One Direction and Miley Cyrus to Keanu Reeves and Johnny Depp. 

In this article, I’ll share different tips about how to wear a beanie — so you can look like more than just a hipster.

How To Wear a Beanie Like a True Fashionista

a woman wearing beanie

Before we get to tips for wearing a beanie, let’s first discuss the basics. A beanie is a hat made of a knitted material like wool, acrylic, or felt. It has a round shape and typically covers the top of your head. It may also have a small cuff around the bottom edge, which can be folded up or down depending on how you wear it. 

The best part about a beanie is that it goes with almost anything. You can pair it with your favorite jeans and t-shirt or dress it up by adding some layers underneath — the possibilities are endless!

Experiment With Different Types of Beanies

Since there are many different types of beanies, find the one that best fits your style. Here are some options to consider:

Cuffed Beanie

A cuffed beanie is one where there is extra material around the bottom of the hat that can be folded over or tucked into itself. This type of beanie is perfect for those who have long hair or just want their ears to be covered up during the cold winter months. These beanies come in many different colors and patterns, so you can choose one that best fits your style. 

Cuffless Beanie

With this type of beanie, there is no edge around the bottom. Instead, it’s completely flat at the bottom and goes straight across without any folds or cuffs. These beanies are also incredibly comfortable because they don’t constrict your head when you put them on.

Earflap Beanie

The earflap beanie is similar to the cuffless beanie, except it has an ear flap that covers your ears when you put it on (hence the name). Often featuring a fleece lining, this beanie is ideal for winter because it provides warmth while keeping those annoying flyaways at bay.

Pom-pom Beanie

Also known as bobble hats, the pom-pom beanie is the epitome of free-spiritedness. This type of beanie has a soft, fluffy ball at the top, making it look even more stylish. You can wear this hat with your hair down or up in a ponytail to show off your new accessory.

Slouchy Beanie

If you’re looking for something more classic, a slouchy beanie will do the trick. These slightly loose beanies are great for casual days out as they are very comfortable to wear. The best part? They also help make a fashion statement. Good for whether you’re out running errands around town or on the slopes.

Consider Your Face Shape

Your face shape will heavily influence the way you wear a beanie. For example, if you have a round face shape, consider wearing a beanie with a wider brim to balance out your features and give off a more angular impression. If you have a square face shape, go for a beanie with a narrow brim that won’t accentuate your jawline but will draw attention to your eyes and lips. 

If you have an angular face shape, consider wearing a beanie with a more pointed or tapered shape rather than one that is straight across the top of your head. This will give you more of an accentuated look and allow you to show off your cheekbones. 

If you have an oval face shape — well, that’s cool for all kinds of beanies.

Rock It with Different Hairdos

men wearing beanies

If you’re one of those people who think beanies are only for people with short hair, you might want to rethink your stance.

Beanies have come a long way since their old-school days as under-the-bonnet headwear. Nowadays, you can rock your beanie with various hairstyles and hairdos — whatever the occasion may be.

If you’re going to an event where you need to look polished and neat but still want to have fun, pairing a beanie with an updo could be a great choice. 

Wrap your hair in a bun or top knot before putting on your beanie, and voila! You’ll look like a total babe without even trying. Just make sure not to overdo it with too much volume or height. 

On the other hand, if you’re heading out for casual fun with friends and want to keep things simple and relaxed, try wearing a beanie with your hair down. It’s fun and funky! 

You can also add some loose curls to your hair before you put on the beanie to make it look more playful.


man wearing beanie

Your beanie is the perfect accessory for your outfit, so why not add a few more accessories to make it even more exciting? You can wear it with your favorite pair of earrings and some dangly necklaces for an added touch of elegance. If you’re feeling more casual, opt for a simple necklace and wear sunglasses instead.

When it comes to the color of your accessories, try and match them with the colors in your beanie. For example, if you’re wearing an eye-catching red beanie, then go for gold earrings. If you’re wearing a black beanie, then keep the rest of your accessories neutral, like brown or beige. 

Try not to go overboard with the accessories. You don’t want to look like you’re trying too hard, and the beanie is just an afterthought. Instead, choose one or two pieces that will complement your outfit.

Pro Tips for Amping Up Your Style

Want to stand out from the crowd and look cool this winter? Try out these styling options:

  • Pair your beanie with a leather jacket and Chelsea boots for a Western cowboy look.
  • Wear your beanie with a pair of leggings and a long-sleeved shirt for a casual, urban style. 
  • If you’re wearing a suit or blazer, try pairing it with a beanie in neutral colors like black, gray, or navy. This will keep your look professional but still fun.
  • Take your outfit from casual to sporty by wearing a beanie with ripped jeans, a bomber jacket, and vans. 
  • If you’re looking for something more comfortable for running errands or doing chores around the house, try pairing your beanie with your sports bra and joggers. This outfit will keep you warm while also giving you movement freedom! 
  • Thinking about attending Coachella with your friend? Wear your beanie with a cute skirt or a floral dress for a stylish, easygoing look!
  • If you’re going out on the town, try pairing your beanie with your favorite pair of leggings and a tank top. It will help keep your hair out of your face while you dance the night away at that trendy new club downtown.
  • For a super chic look, wear your beanie with a turtleneck sweater, a long coat, and jeans or chinos.

Wrap Up!

Whether you’re looking to express yourself in a new fun way or just want to stay warm this winter while still looking stylish, beanies are the way to go. 

When it comes to choosing a beanie, your best bet is probably to find one that’s unique and flattering to your face shape. Once you have that down, you can focus on choosing a style that fits your personality and lifestyle. 

From there, it’s just a matter of finding one that you love and wearing it proudly. And with my advice on how to wear a beanie with different outfits, you’ll be able to walk out in the cold with your head held high!

For more styling tips and inspiration, check out my blog and follow me on Instagram for daily updates!

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