The Ultimate Men’s Guide to Wearing a Beanie

When it comes to fashion, hats are tricky to pull off. Figuring out the balance between function and fashion is difficult for anybody, but men face the extra challenge of limited options. After all, it can sometimes seem like men’s options for accessories are all outdated, cringe-worthy, or just plain boring. Luckily, beanies are a fantastic and easily accessible option that you can complement a wide variety of styles and outfits.

Unsure about where to start? Check out different options, styles, and outfit tips with our ultimate men’s guide to wearing a beanie.

Know Your Options

The trick to pulling off a beanie is to choose the right style. You can’t just grab the first wool hat you see on store shelves. Instead, find a beanie style that complements your hair and your wardrobe. Below are a few of the most popular types of beanies that work with a variety of outfits and styles.

Cuffed Beanies

The cuffed beanie is the traditional beanie style. This classic look features ribbed material and a thick, even cuff around the base of the hat. The cuff adds a bit of visual interest, breaking up the otherwise uniform look of the beanie. It’s also an important functional feature, as the double layer offers extra warmth around your ears.

Fishermen Beanies

Fishermen beanies originate with dock workers. As a result, they boast a serious, working-man look. Fishermen beanies are shorter than a lot of other options. They sit high on the head and usually rest just above the ears. This means they don’t offer the best cold protection, but they make up for it with a clean look that works for sharp-dressed men and chic hipster icons alike.

Slouch or Baggy Beanies

Longer slouch beanies are easy to spot in craft breweries, college art buildings, and anywhere else that attracts a hipster crowd. The slouch beanie offers a more relaxed, casual look that’s perfect for hanging out on your day off. Baggy beanies don’t feature cuffs, but the excess material allows you to fold your own cuff into the hat to accommodate that style.

Because they’re longer, slouch beanies usually sit halfway over your ears and offer more warmth in the cold winter months. However, this beanie style sometimes requires precise positioning to ensure it looks cool and stylish rather than bulky and awkward.

Bobble Hats

Bobble hats—also known as pom-pom beanies—are the perfect cozy option on the coldest days of the year. This beanie style is more fun and casual, so it won’t work with your formal office look or serious streetwear. However, there’s no better option when you’re hitting the ski slopes or exploring the winter trails.

Wearing a Beanie With Long Hair

Now that you know what options are available, one of the best tips for wearing a beanie for men is to work around and highlight your natural hairstyle. Therefore, if you have long hair, use your beanie to show off those signature locks. Letting your hair flow loosely beneath your beanie is the perfect way to frame your face and keep your neck warm. Best of all, the beanie will help keep everything in place once you style your hair, so you don’t have to worry about adjusting and readjusting all day long.

Furthermore, choose a longer beanie—like a slouch beanie, a bobble hat, or a larger cuffed beanie—so you can pull it further down your head. This will also prevent your beanie from feeling too tight or looking stretched out.

Wearing a Beanie With Short Hair

If you have short hair—or if you’re rocking a bald or shaved head—a beanie is the perfect way to stay warm and stylish all winter long. Just make sure your beanie isn’t overpowering your head. Choose a shorter beanie or a style with a tighter fit to maintain a slim, fashionable look. Cuffed beanies and fishermen beanies are perfect for this, but you might want to find ones with thicker materials, so you don’t sacrifice warmth for style.

Tips for Curly Hair

Are you worried about ruining your natural curls with a heavy hat? Don’t be! Short- and medium-length curls look great framing your face beneath a beanie. So resist the urge to tuck your hair away and instead let your curls add visual interest to your forehead and around your ears.

Just make sure you choose a bigger, looser beanie, so you don’t flatten your hair. Slouch beanies are a perfect option because they give your curls more room to breathe beneath the hat. This lets you show off your beanie style without ruining your hair for the day.

Dressing Sharp With a Beanie

Beanies aren’t the most formal accessories in the world, but that doesn’t mean you can’t pair them with a smart outfit. Whether you’re braving the cold on the way to work or dressing up for a more formal occasion, you can make your look unique with the right beanie.

Stick to thinner, more fitted beanie styles such as traditional or fishermen beanies that sit higher on your head. Don’t worry about choosing between cuffed or uncuffed options—both can look great with a suit or dress shirt. Finally, choose solid colors and avoid patterns to maintain a smart and serious look. Neutrals often pair best with a formal look, but you can also add a pop of color if the occasion calls for it.

The Rugged Outdoorsman Style

Beanies are perfect for a sporty or outdoorsy style. Lean into function by choosing a hat with a thicker material that will keep your head warm while you’re out and about. When looking for the right beanie for your casual or outdoorsy style, the world is your oyster.

For colder winter days, a bobble hat is the perfect way to stay warm, cozy, and stylish. A slouch beanie is also a versatile choice for any casual outfit. Pair your beanie with other casual yet fashionable outdoor menswear to create a look that will make you look and feel good wherever your adventures take you.

When it comes to blending fashion and function, YoColorado is the place to shop. Check out our selection of Colorado menswear to find the perfect beanies and other clothing and accessories to complete your winter wardrobe.