The Best Hipster Beanie Styles

Can you call yourself a hipster if you don’t have a carefully curated collection of beanies designed to convey artfully that you don’t care about your appearance?

Yeah – we didn’t think so. If your only beanies are from your childhood (wait, that might actually be kind of cool), you’ll need to fill out your collection with a few staple pieces.

Not all beanies are created equal, and they don’t all look alike. If you want the ultimate collection for your hipster looks, you’ll need a nice variety to cover each essential outfit type.

Let’s take a look at these hipster beanie staples.

5 Hipster Beanies You Must Have

Here are the top Hipster beanies you’ll see in the wild. Each one has a purpose, and each must be styled in just the right way. In some cases, you’ll have to perfect something called “The Helix,” a styling choice that sees your beanie perched directly on the top of your head as if you’ve just come in from a long day on the trawler.

You aren’t ready to take your hat off, but your ears need to breathe. Choose carefully.

The Fisherman’s Beanie – Your Effortless Cool

hipster beanies

Fisherman’s beanies used to be a dock-worthy hat designed to stay out of the way while keeping the head warm during cold fishing seasons. The sea is a cruel mistress, but you don’t ever have to set foot on a trawler to get some use out of this hat.

The Fisherman fits tightly around the head and covers just the top of the ears with a wide cuff. It’s a soft knit and typically comes in neutral colors like gray or brown.

To style it with some serious fun, get a red one just like Steve Zissou or go for a bright orange.

The key here is to allow it to sit on the top of your head without covering the ears or just tucking the tips of your ears underneath the chunky cuff. It sits squarely on the head – no tilting – and you’ll need a ton of confidence to pull it off since it really doesn’t serve much “winter weather” purpose.

When you’re adding this to your outfit, think of it like a baseball cap, but with a softer, cozier aesthetic and no association with those jocks of your high school years.

It can complete an outfit that says “yes, I’ve worked in labor” but fits well with that vintage peacoat you scored for next to nothing at your local thrift shop.

To get the look of the Fisherman, take some cues from Wes Anderson’s movie and check out the Beechfield Unisex Trawler. It comes in both neutral colors for those of you who want a hat to go with everything and a fun, bright yellow or unexpected plum for a pop of interesting color.

Beechfield B460 Trawler Beanie Hat Black
  • 100% soft touch acrylic fabric.
  • Ribbed knit
  • Retro styling

The Slouch Beanie – For a Head Full of Hair

hipster beanies

The Slouch Beanie, made famous by David Beckham, is a beanie style meant to hide everything you’ve got. It offers the same soft, cozy knit that all beanies have but with no cuff and lots of room to stuff that hair you’ve been growing out.

You may not even have to take out your man bun.

Man bun aside, this beanie offers more coverage and tends to stay in place a lot easier than some of our helix styles. If you can’t stand adjusting your beanie all day so that it sits “just so” on your head, the Slouch might be the one for you.

When you’re styling the Slouch, it goes well with actual winter gear – think scarfs and heavy overcoats.

However, we won’t knock the aesthetic appeal of a rolled-up button-down with some tattoos peeking out and a slouch beanie that hides either a full head of hair or something artfully shaved. No lie, there’s something pretty appealing about a mystery.

This is where hipster women can also get in the beanie game with a slouch that can sit on top of the hair and accentuate the face or tuck hair into it for protection against the wind and snow, keeping curls and braids in top shape.

Take some styling cues from David and check out this versatile Slouch from Vecry. It comes in a variety of colors, including both neutral and statement choices, and it offers plenty of material to style the slouch with just the right amount of elasticity.

VECRY Men's Cool Cotton Beanie Slouch Skull Cap Long Baggy Hip-hop Winter Summer Hat (Black)
  • Mens Slouch Knit Beanie Hat ( You Can Choose Fulfilled by Amazon : Prime)
  • SIZE: One size fits most. Fit M~L (22.05inch ~23.6inch) head circumference and combines plenty of stretch with a snug. Flat-size: length: 12 Inch, width:10 Inch.
  • MATERIAL: High quality material Acrylic & Polyester , Comfort,breathable and excellent elasticity will stretch to fit most head sizes.

The Bobble Beanie – Revisiting Childhood

hipster beanies

Hipsters love revisiting vintage pieces from the past, and this could be just the chance you need to get out that super vintage, Bobble topped beanie your mom saved from your childhood. With any luck, it smells like cedar from her cedar chest.

If not, you still have plenty of chances to find a Bobble. These look best for the weekend when you’re likely to be wearing your favorite flannel or your hiking gear.

Bobble beanies usually have a nice cuff and enough fabric on the top that the Bobble feature is able to sit nice and high.

Bobble beanies look great in neutral colors, but they really shine with some bright colors and patterns. If you’ve got a vintage sports one with 1980s colors, you’ve won the game. If you can get your hands on one that screams ugly holiday sweater, you’ve also won.

Don’t discount the appeal of a classic gray or black, however.

Bobble beanies are fun and can both hide some hair or helix well if you roll the cuff pretty high. Sit the beanie just above your ears for the ultimate helix or pull it down to protect from cold temps when the wind is brutal. This one from Beechfield is a winner.

Beechfield Fair Isle Snowstar Beanie French Navy/white O/s
  • Timeless Fair Isle pattern.
  • Classic Styling.
  • Cuffed design for optimal decoration.

4. The Cuff Beanie – No Fuss, No Muss

hipster beanies

Yes, most of the beanies we’ve shared have cuffs, but a classic cuff beanie has no gimmick. It’s just cuff and the right amount of fabric — no Bobble.

No slouch. No fisherman knit. It exists as the Plato ideal if you will.

The basic cuff uses a moderate cuff roll to fit the beanie directly over the ears for a warm aesthetic and to hide any terrible hair days you might be having.

From there, you can roll it down for a baby slouch or roll it up for the helix of your dreams. It’s the one beanie to rule them all.

With the right amount of swagger, you could almost get away with wearing a cuff beanie and your formal wear (almost). You can definitely pair it with jeans, sweats, and office wear if your office is in a startup housed in a former warehouse downtown.

It’s versatile, and every person, man, woman, child, alien, needs one.

Whether you’ve got colors on your mind or neutrals all the way, the classic cuff beanie is there for you. We love the classic story behind the Carhartt beanie.

It comes from a company that’s made work gear since the late 1800s and is a staple for working-class fortitude. You really can’t go wrong with that kind of history.

The Visor Beanie – Embrace the Yuppie

Original One Winter Wool Knitted Chunky Visor Beanie Hat with Brim Fur Lined Peaked Ski Cap (Black)

The Visor beanie is a structured style with a thin visor that goes directly across the eyes. There’s no cuff, no helix, and no slouch. It’s all business and all downhill skiing.

In other words, it’s the perfect beanie for ironic wear and so rocking it out fully with your thrift store finds on the way to your small roast coffee place is an excellent option. It does scream bad guy in a snow movie, but pair it with your favorite hipster mustache or your slouchy boots, and you have yourself a winner.

Visor beanies are best in neutral colors, and our particular color of choice is a gorgeous navy. Women can also get into this type because the structure makes it easier to style hair underneath.

It also looks great for times when you’ll be out with your coworkers building company morale in some kind of escape room exercise. Business in the front – irony in the back.

Get the look with this Original One Chunky Knit Visor Beanie. It offers just the right amount of stretch with a visor that’s not too big. The knit provides two different textures for interest and allows you some adjustments for different sizes of heads and hairstyles.

Original One Winter Wool Knitted Chunky Visor Beanie Hat with Brim Fur Lined Peaked Ski Cap (Black)
  • Material--70% Acrylic,30% Wool(Keep you warm on frigid cold winter days. No Scratchy or Itchy to Your Skin)
  • Size--This winter visor beanie fits 21-23.5 inch head circumference and stretch freely and comfy wearing.Stylish and classic.
  • Fit style--This billed beanie is great for winter and fall.Suitable for daily wear for men and women.Suitable for indoor or outdoor wear.Such as...

The Value of the Beanie

You cannot style an outfit without considering a beanie as a hipster. They’re versatile, ironic, and offer plenty of “just walked out of the house like this” appeal that can either hide or accentuate your features.

Beanies are some of the most comfortable accessories on this planet, and can really help you get through the cold in some of the most significant hipster places in the world.

Is Seattle too rainy? Beanie. Portland cold getting to you? Beanie.

On the lake or out hiking to reconnect with nature? That’s right, beanie.

Making a statement on your bike? The only choice – a beanie. Once you’ve chosen a few, you may never go back to regular hats again.

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