Isn’t It Ironic: The Best Hipster Hats

You might think that hipsters are a phenomenon of modern pop culture spurred by millennials living in Brooklyn, but the term "hipster" has been around since the early 1900s. Derived from the word "hip," it was used as a way to describe someone who was "in the know" and highly apprised of culture that existed outside the mainstream.

But as with many words, the term "hipster" and its connotations have evolved over the years. In the 1940s, it was primarily reserved to describe jazz aficionados, also called "hepsters" and "hepcats." In the 1950s, it was the beatniks who pored over the pages of poets like Jack Kerouac while donning black turtlenecks and berets. In the 1960s, it was the hippies of the counterculture youth movement who espoused free love, diversity, and pacifism.

Today, hipsters are often considered a self-obsessed lot, inordinately fussy about fashion, music, food, artisanal anything, and indie everything. We’ll admit that such a generalization isn’t entirely untrue, but we say, live and let live.


Isn’t It Ironic: The Best Hipster Hats

We're not going to judge you for earnestly drinking nitro cold brew with oat milk, ironically chugging PBR while listening to Mumford & Sons (on vinyl, of course), getting your tenth triangle tattoo, donning horn-rimmed glasses even though you have 20/20 vision, or paying $100 for vintage concert T-shirts.

We just want you to enjoy wearing a hat that offers the style and substance to make you look and feel your best. To that end, here are the top hipster hats for men and women along with the important do's and don'ts of wearing them.

Fedora Hat

Isn’t It Ironic: The Best Hipster Hats - Fedora

If there's one hat style that has become synonymous with today's hipster, it's the fedora. Relentlessly ridiculed as some sort of colossal offense to humanity, never mind fashion, the fedora has gotten an undeserved bad rap. After all, it's just a hat. And a really cool hat, at that.

Often mistaken for the tiny-brimmed trilby, a fedora features a pliable mid-sized brim and a center crease pinched on both sides. While wool is the most popular fabric for cold weather, you can opt for a straw hat version during the warmer months. Try the St. Pierre wool-felt fedora by Brooklyn, a bestseller for men and women that offers a soft-hued option to basic black or brown. To pull it off perfectly, check out our guide on how to wear a fedora.


Isn’t It Ironic: The Best Hipster Hats - Fedora style

Do:

Wear your hat the way it's intended to be worn. That means with the sweatband at the center of your forehead or slightly higher or lower, as pictured above, with the impossibly cool straw Panama hat by Scala.

The main thing is that it's comfortable, sits above the eyebrows, and feels snug enough that you don't have to adjust it every five minutes.

Isn’t It Ironic: The Best Hipster Hats - Styling tips

Don't:

Wear your fedora halo-style. This means wearing it toward the back of your head where it can easily fall off. While men are not immune to trying this trend, it's primarily a fashion crime committed by women. Wearing a hat halo-style not only looks silly, but it's simply not practical and exemplifies the height of trying-too-hard hipsterdom.


Knit Beanie

Isn’t It Ironic: The Best Hipster Hats - Knit Beanie

Hipster or not, beanies are a favorite hat year round thanks to their utility, ease, and universally flattering appeal for any face shape. While a slouchy beanie epitomizes hipster style with its insouciant design, there are other options when it comes to these knit caps.

Fisherman beanies have thick ribbing and a wide cuff while other close-fitting beanie hats might feature other embellishments such as the sequins on Scala's Alpine acrylic knit cap. For more options, browse our guide to the best slouchy beanies.


Isn’t It Ironic: The Best Hipster Hats - Beanie tips

Do:

Consider the occasion. If you're hanging out with friends, glamping, running errands, or walking your pet ferret, throwing on a slouch beanie or any other type of beanie is perfectly acceptable, as long as it's not a heavy-knit beanie in the middle of summer.


Isn’t It Ironic: The Best Hipster Hats - Beanie style tips

Don't:

Wear a non-slouchy beanie above your ears and high on top of your head so that it has extra material peaking at the top. It's not a good look. Also, don't wear a beanie hat to the office, dinner parties, or your best friend's wedding even if it's at a barn and the bride and groom are both wearing Chucks.


Flat Cap

Isn’t It Ironic: The Best Hipster Hats - Flat cap


Also referred to as an ivy cap, a flat cap is slightly rounded with a low profile and a small, stiff brim. More formal than a baseball hat and more casual than a fedora, flat caps don't endure the same hipster scorn as the latter. Perhaps it's because this hat style is more understated and takes up less space.

Although they remain more popular in the U.K. where they originated, flat caps are steadily becoming a wardrobe staple for men in the United States and worldwide. They're also growing in popularity as a women's hat. Because they are usually constructed from tweed or cotton, they're a smart winter hat.


Isn’t It Ironic: The Best Hipster Hats - Flat cap style tips

Do:

Keep it simple and classic. Opt for a tweed ivy cap in the fall or a lightweight cotton version in the spring and pair it with a monochromatic ensemble that forgoes too many hipster trends. Translation: When wearing a flat cap, ditch the bow tie and suspenders, and for goodness' sake, shave that beard! (Just kidding. Not really.)


Isn’t It Ironic: The Best Hipster Hats - Flat cap tips

Don't:

Be afraid to have fun with color, texture, and pattern. As long as you choose coordinating color-blocking or prints for the rest of your wardrobe, an ivy cap can add a fashionable finishing touch. Don't miss out out even more must-have tips with our guide on how to wear an ivy cap.


Baseball Hat

Isn’t It Ironic: The Best Hipster Hats - Baseball hat


For a casual day out, it's hard to go wrong with a tried-and-true baseball cap. While there are some slight differences among the snapback cap, strapback hat, and fitted ball cap, the one that is typically associated with hipsters these days is the snapback cap with its broad bill and wide, structured profile that comes in an array of colors and designs.

Also gaining ground is the dad cap — slightly oversized baseball hats with a low profile, slightly curved bill, and distressed finish. But the one hat hipsters should not revisit is the trucker hat. The trucker cap shot to fame back in the early 2000s when Ashton Kutcher never left home without one. Read more of our do's and don'ts of baseball hats.


Isn’t It Ironic: The Best Hipster Hats - Baseball cap tips

Do:

Find a baseball cap with a good fit that fits comfortably and securely without risk of falling off. Have fun mixing things up with unexpected fabrics such as satin or understated accents like metal grommets. Baseball caps don't have to be boring.


Isn’t It Ironic: The Best Hipster Hats - Trucker hat

Don't:

Wear a baseball cap sideways. And no matter how ironic you think you're being, don't wear a trucker hat. These mesh monstrosities already had their heyday, so let them rest in peace.


Hip, Hip, Hooray

Isn’t It Ironic: Best Hipster Hats

Whether or not you embrace or abhor the hipster moniker, the bottom line is that there's nothing wrong with wanting to resist elements of mainstream culture. It's how we learn and grow.

When it comes to fashion, just remember to find balance and avoid going overboard with trends. Peruse our selection of new arrivals for both men and women and find what makes you feel your best. After all, confidence is the key to pulling off any look.


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