Seven Hipster Hats for all Seasons

You’ve spent hours agonizing over the perfect flannel to go with your vintage Levi’s that were made during the Eisenhower administration. You’ve laced up your decidedly not-for-combat boots as you prepare to head over to your local artisanal pour-over coffee spot. But are you really ready to go? No, not without the perfect hat.

But what defines hipster headwear? Hipster hats are inspired by current trends in streetwear, vintage nostalgia, and classic craftsmanship. Think a slouchy baseball cap with an emoji on it, or a newsboy cap that harkens back to The Great Gatsby.


Applejack Newsboy Cap

applejack newsboy cap

Brixton Oath III Hat

brixton oath iii hat

Beechfield Unisex Trawler Beanie

beechfield unisex beanie

The Most Hipster Hat Styles

Today, we’re going to take a closer look at some of the freshest styles for any occasion. That way, you can ensure that even the most disinterested and unaffected hipsters in your neighborhood can recognize your stylistic greatness.

Whether you’re keeping your head warm or looking to accent your outfit, a hat is always a winning accessory. Let’s take a look at a few of your best bets.

Channel the '20s With a Newsboy Cap

A classic style that’s been relatively unchanged since it was first created around the turn of the 20th century. The newsboy or newsie cap is basically an eight-panel flat cap that can be made in a variety of materials. Most newsboy caps are made from tweed or wool, and some feature common suiting patterns like pinstripes, chalk stripes, or plaid.

Over the years, newsie caps have been associated with everyone from newspaper boys to dockworkers, beggars to artisans, and everyone in between. Today’s styles aren’t just for men, either, and fashion houses have been making stylish alternatives for ladies as well.

These caps do a great job of bridging the gap between casual and formal. While the shape and style of the cap are decidedly relaxed, they're often made from suiting fabrics, which adds a much dressier element to the look. So, whether you’re running errands, out on a date, or looking for a hat to complete your look at a wedding or formal affair, look no further than the newsboy cap.

This classic newsboy cap is updated in a breathable linen fabric, making it perfect for practically any scenario, including hot summer days when you’d be sweating bullets if you wore a wool or tweed version.

Applejack Newsboy Cap

applejack newsboy cap

This Applejack newsboy cap is made of 100% Linen. It is well constructed and looks stylish, beautiful, and it features a classic 8 panel design with a front button snaps to visor and has a classic style feel to it. This newsboy cap will compliment your winter or daily headgear accessories.

Snapback to the ‘90s

Made famous in the ‘90s, snapbacks solidified their place in pop culture through shows like the Fresh Prince of Bel Aire. Snapbacks have gone in and out of fashion over time, but 90's nostalgia has resurrected it back into the public eye.

Snapbacks typically are made from wool, polyester, or cotton, and feature a high crown and a flat, uncurved brim. How you style your snapback is up to you. Often, the brim is left uncurved, and most people prefer to wear it either backward or forwards.

Whatever you do, don’t wear your snapback sideways, unless you’re trying to channel the ghost of Kenny Fisher from Can’t Hardly Wait. We love this updated snapback from Brixton Supply Company as it blends a variety of premium materials to create a stylish hat that’s perfect for any casual scenario.

Brixton Oath III Hat

brixton oath iii hat

The Oath III is one of the original snapback styles. Featuring a medium profile, six-panels, and a custom-embroidered patch, the Oath III delivers the fit, feel, and look you want, every time.

The Ultimate Hipster Headwear: Knit Beanies

Anyone, and we mean anyone, looks great in a knit beanie. They have been the official hipster headwear since Richard Dreyfus’ rocked one in Jaws. They transcend trends and style, and you'll always look great wearing one.

From oversized slouch beanies to fisherman’s caps, there are tons of different beanie styles you’ll find in stores. The key to wearing a beanie is selecting the best one for your face shape and style.

One hipster staple is the fisherman cap, which features a thick ribbed design and cuffs up over your ears. In colder weather, flip the cuff down to keep your ears warm. Another popular style is the slouchy beanie. These beanies are purposely oversized and are designed to be worn off the back of your head.

Beechfield Unisex Trawler Beanie

beechfield unisex beanie

The Beechfield Trawler Beanie features a 100% soft touch acrylic fabric, ribbed knit, and retro styling.

You’ll also find other options that reside somewhere in between the short fisherman’s cap styles and the extra-long slouchy beanies. We love this fitted fisherman’s cap from Beechfield for its effortless hipster cool. Or, if you’re looking for an even more casual style, check out this slouchy beanie from Amazing J.

Multicolor Beanie

multicolor beanie

High quality material acrylic wool yarn materials - super comfortable and lush for lasting warmth and softness. Will keep you warm on frigid cold winter days. Not scratchy or itchy to your skin.

While everyone looks great in a beanie, that doesn’t mean you should be wearing one at all times. While they’re more than appropriate for hanging out, running errands, or a Friday night at the bar, you’ll probably want to leave your beanie behind when it’s time to go to the office, or anywhere with some semblance of a dress code.

Bring on the Dad Vibes

When it comes to trendy headwear, the iconic “dad hat” has been popular amongst hipsters for a while now. This style of baseball cap was once reserved for nerdy dads mowing the lawn on Saturdays. However, they’ve since been adopted by everyone. From hip-hop’s elite to the cute girl who works at the vintage record shop up the block, the dad hat has quickly become their preferred headwear.

As the dad hat continues to grow in popularity, there’s virtually no end to the colors, patterns, and graphics available. From sports teams, to emojis, to everything in between, the dad hat has become a standard method of expressing your personality. This emoji-fied version from KBethos makes a great choice, no matter your style, and it’s available with tons of different graphics.

Pineapple Baseball Cap

pineapple baseball cap

Premium soft cotton material. Long lasting durability. Lightweight and breathable.

Dad hats are usually available in cotton or polyester, although you’ll occasionally find wool and other materials as well. As a rule of thumb, the less structure to the hat, the better it will look on your head. Due to this, try to avoid hats that have overly-structured panels.

Dad hats are an easy way to inject some much-needed style into any outfit. With dad hats, the same rules that apply to snapbacks and baseball caps apply as well. The most important is: don’t wear it sideways, and don't wear it to formal occasions.

Get Campy With A Five-Panel Hat

Five-panel hats are similar to baseball hats but utilize a completely different construction style to cast a more interesting silhouette.

Unlike a baseball cap that has six equally sized panels, five-panel caps are slightly different. They feature a front panel, side panels, and a top and back panel. Whether you’re looking to channel Sidney Deane in White Men Can’t Jump, or you’re looking to capture some of that “bike messenger from Williamsburg” swag, a five-panel cap is a great way to do it.

hatphile camp cap

This high quality cap is trendy and stylish, and is perfect for any outdoor activities such as camping.

These caps are adjustable and usually feature a buckle closure. Supreme helped put the five-panel caps on the map with their tonal versions, but five panels also look fantastic in bold, vacation-ready prints and patterns. Like this southwest inspired version from Hatphile, which is available in tons of different colors.

While five panels offer slightly more structure than a dad hat, that doesn’t mean you should be wearing one to a black-tie affair. But, if you’re out running errands or meeting friends for drinks, a five-panel cap is an easy way to inject some style into any outfit.

The Quintessentially American Baseball Cap

For well over a hundred years, the baseball cap has defined casual American style. Whether you’re on the field, off the field, or even if you’ve never even seen a field, a baseball cap is always a great look.

San Diego Hat Company

san diego hat company

This hat is imported, 50% polyester, 50% rayon, trendy and fashionable.

We recommend leaving the team hats to the pros in favor of a more refined hat made from wool, felt, or cotton to strike a look that’s less reminiscent of The Sandlot. This sophisticated wool version from the San Diego Hat Company perfectly blends classic American style with a touch of class, care of its wool construction.

Refine Your Style with a Porkpie Hat - Yes, It’s Really Called That

Its an odd name for a hat, but its been the go-to headwear for dapper people since the 1800s. The Porkpie came back into favor thanks to Popeye Doyle from The French Connection. Thankfully, it’s been a favorite of discerning hipsters ever since.

Turn on an episode of Mad Men, Boardwalk Empire, or any other period piece, and you’re sure to see a porkpie hat or two gracing the heads of the most stylish gentlemen on the set. Of course, you don’t have to be wearing a suit to channel some refined sartorial vibes with a porkpie hat.

Today’s takes on the classic style fit in at the coffee shop or on a dinner date as they would with a suit and an overcoat. However,  the coolest way to wear one may just be with jeans and a white t-shirt.

Porkpie Hat

porkpie hat

Lined with satin and a 16-ligne grosgrain, this hat stands out from any run-of-the mill derby and ensures you can be the life of the party wherever it may be.

This well-designed porkpie from Scala is a fine example. Crafted in period-correct felt, this cap looks great whether you’re wearing a suit, sportcoat, or just a t-shirt. Styling one may seem difficult at first. However, pulling off a porkpie hat is just as easy as wearing any other hat.

Final Word

Whether you’re looking for a dad hat, a beanie, a snapback or porkpie, finding the perfect hipster hat isn't hard. Start with our style guidelines above, and as you feel more comfortable, step outside the box and wear your new hat however, you feel most comfortable. Whichever style you choose, it’s sure to look great.

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