Eleven Stylish Hipster Shirts

When you think of hipster style, you probably picture crazy hats, long scarves, and tons of accessories. However, there’s far more to the hipster look than many people realize.

Must-Have Hipster Shirts Suitable for Work and Play

Probably the most mainstream, versatile example of hipster style is hipster shirts. From ironic print T-shirts to elegant long-sleeves, hipster shirts are perfect for a variety of occasions. Combining trendiness with fun and an ironic sense of detachment, hipster shirts have lots to offer.

Today, we’re taking a closer look at hipster shirts you can add to your wardrobe to update your style:

Whether you’re 100% committed to hipster style or just want a slight upgrade to your wardrobe, here are some excellent options to choose from:


hipster shirts

Pick ten random people on the street and ask them to describe the hipster style. The chances are good you’ll hear the word “plaid” more often than not. It’s often considered the quintessential hipster look.

Plaid long-sleeve shirts can be worn in many different ways:

  • Tucked
  • Untucked
  • Open
  • Buttoned-Up

Even better, plaid fits in practically everywhere. Tucked and buttoned, you can wear them in a business-casual office. You can also wear them open over a plain tee for a night out drinking PBR in a dive bar.

Although it rose to popularity during the grunge era of Generation X, hipsters put a signature spin on plaid shirts to make them all their own. Instead of the dirty, oversized look favored by Kurt Cobain and Eddie Vedder, hipster flannel is worn with a tighter, tailored fit.

Although artisanal plaid shirts are often seen as the most authentic option, the beauty of plaid shirts is that the expensive ones and the budget-friendly ones all look fairly similar. A basic long-sleeved plaid flannel keeps you fashionable without busting your budget.

Of course, a key element to hipster style is taking existing fashions and subverting them – like this bold, multi-colored flannel from LifeHe. For the ladies, this green-and-gray flannel from Zeagoo is fun and colorful.

Amazon Essentials Men's Regular-Fit Long-Sleeve Plaid Flannel Shirt, Yellow, X-Small
  • Allover plaid and midweight flannel make this button-up shirt a go-to pick when the temperature drops
  • Patch chest pocket, rounded hem and barrel cuffs
  • Same fit, new name: We’ve changed the name of this shirt style to “Regular Fit” but the measurements remain the same

Printed Tees

hipster shirts

The ironic printed T-shirt is a hipster mainstay. As with anything related to hipsters, the more obscure, the better.

Hipster shirts feature a wide range of images and logos from old TV shows, indie bands, and even brands from decades ago, such as Polaroid and MTV. (Of course, MTV still exists, but the logo refers to the early 80s version of the channel.)

Mad Engine Men's Classic Polaroid Logo Vintage Style Rainbow T-Shirt, White, Small
  • Official classic polaroid vintage-inspired logo with rainbow, men's sized t-shirt by Mad Engine
  • Simple, classic vintage-style polaroid rainbow logo design
  • Perfect for fans of the first instant-print camera and those who appreciate the art and nostalgia of polaroid

Hipsters also love band shirts. The most popular shirts feature popular rock bands from the 60s and 70s, such as Pink Floyd, Led Zeppelin, and Lynyrd Skynyrd. Some hipsters take it up a notch with heavier bands such as Metallica and Slayer.

Tight Tees

hipster shirts

Hipsters are generally known for having a thin, even emaciated body type. They’re usually not jacked or overweight. This body type often translates to the size of clothing worn. Typically, hipsters wear shirts that are either tight or loose. A standard-fit just isn’t the hipster style.

Any plain tee gets a hipster makeover if you wear it just a size too small. For example, these plain black shirts from Gildan have a decided hipster flair if worn tight and untucked.

Gildan Men's G2000 Ultra Cotton Adult T-shirt, Black, Medium
  • Seamless double needle collar
  • Taped neck and shoulders for durability
  • Double needle sleeve and bottom hem


hipster shirts

At the heart of hipster style is an ironic appreciation for styles from other eras and purposes. Styles from different eras are co-opted with a wink. In many ways, the person wearing the clothes defines the “hipsterness” of the style. For example, what looks appropriate for a man in his eighties takes on a distinctly hipster-vibe when worn by a 20-something city dweller.

Male hipsters gravitate towards suits with old-fashioned cuts, suspenders instead of belts, and various hats (but no ballcaps). Women hipsters tend to favor 1950s-era fashions such as this polka-dot top from Belle Poque.

Women Vintage Office Shirt and Blouse Polka Dots Short Sleeve Buttons Shirt Tops, Navy Blue, Small
  • Belle Poque Women Vintage Polka Dot Shirt Top
  • Turn down collar, short sleeve, polka dot, comfortable material, casual fit, button down blouse.
  • Perfect for daily wear, party, birthday, cocktail, office, formal & informal events and more. Can wear all year round


hipster shirts

Hipsters will spend a fortune on clothing that looks like it was found in a thrift store. Shirts might have worn elbows, holes, or tears. Any logos might appear faded and cracked. The overall style is meant to look effortless and indifferent.

If this is the look you’re going for, check out this black-and-gray ripped T-shirt from Kliegou or this ripped crewneck T-shirt from Urbancrews.

You’re probably saying to yourself, “Why do I want to buy pre-ripped clothing?” Can’t you just cut your clothing yourself, or wait for shirts to wear down on their own?

While that could save you some bucks, the main advantage of pre-worn clothing is that it’s designed to not fray further. Once you get a natural tear in a shirt, it’s only a matter of time before you’re wearing rags. But a distressed shirt retains its look consistently.

Add to the look with pre-worn jeans, available with frayed hems, open knees, and other light tears. However, stay relatively conservative. Avoid wearing torn shirts, pants, and a jacket all at once; it dilutes the effect and ends up looking too sloppy.

URBANCREWS Mens Hipster Hip Hop Ripped Zipper Crewneck T-Shirt SANDWHITE Small
  • Machine Wash Cold with Like Colors
  • Classic Crewneck T-shirt
  • Zipper Embellishment Adorns the Front


hipster shirts

Hipsters love their turtleneck sweaters. Formerly a style associated with stuffy professors, hipsters made turtlenecks cool and popular again. Today, turtlenecks are far too mainstream to be considered alternative, but they are certainly sophisticated and stylish.

Check out this pullover knitted turtleneck from H2H. You’ll stay warm while looking cool on your way to work or when out on the town.

H2H Men's Hipster Hip Hop Hoodie Irregular Zipper T-Shirt Knitted Pullover OliveGreen US 3XL/Asia 4XL (KMTTL046)
  • Style no : #KMTTL046 #KMTTL047 #KMTTL040 #KMTTL041 #KMTTL045 - Turtle Neck
  • Soft decent slim fit, Breathable & Good quality fabric, Turtleneck, Long sleeve and Irregular hem design gives it a fashionable feeling. Suitable for a variety of occasions:...
  • Paired with your casual jeans or trousers, perfect for casual daily, wear to work, holiday, club, pub, street etc.

Hip-Hop Shirts

hipster shirts

Also called – get ready for it – hipster hop, hipster hip hop is both a style and a genre of music. Macklemore and Lil Dicky are two popular examples. Most hipster hop style is identical to traditional hipster style with vintage clothing, printed shirts, and other examples listed above.

However, you’ll also find plenty of hipster hip hop shirts, too. They’re the opposite of the tight shirts described earlier. Hip hop shirts are typically worn large, with long tails and sleeves. It’s similar to the style pioneered by Eminem (although we’re hesitant to label him as a hipster).

These long-sleeved hip hop T-shirts from LIEKIE are a good example of hipster hop style, as are these crewneck short-sleeved shirts from JC Distro.

LIWEIKE Mens Solid Extended Hipster Hip Hop Swag Curve Hem Long Sleeve T Shirt (White, Large)
  • ❤Material:Cotton and polyester fiber.Comfortable,soft and light weighted,safeguard your skin.
  • ❤Feature: Popular all seasonal t shirt. Long drop tail,long sleeve,curved hem,crew neck,men's t-shirt,solid color.Pair up with any clothes will perfectly fit.
  • ❤Occasion:Suitable for casual, work, holiday, club, party, date, outdoors, sports, beach, street, home, etc. Perfect gift for families, friends, boyfriend or husband in...

Bold and Colorful

hipster shirts

A lot of hipster style revolves around plain colored tees. However, when hipsters do decide to add color to their wardrobe, they go flashy and bold. Loud, colorful button-up shirts are a hipster mainstay. Think of loud bowling or Hawaiian shirts but with a vintage twist.

Goodthreads Printed Poplin shirt features a full array of colorful flowers against an aqua-colored background. It’s eye-catching and just the right amount of obnoxious to qualify as hipster-approved. Coofandy’s rose print t-shirt is another example. A more office-friendly version of the style is this black, white, and red short-sleeved shirt from SSLR.

Amazon Brand - Goodthreads Men's Slim-Fit Short-Sleeve Printed Poplin Shirt, Wallpaper Floral, Medium
  • This casual must-have short-sleeve shirt features a button-down collar, patch chest pocket, and box-pleated back yoke. Made in our Signature Tumbled Cotton for a soft, yet...
  • Model is 6'1" and wearing a size Medium
  • Slim fit: closer-fitting in the chest, slightly tapered through the waist for a tailored look

Snarky T-Shirts

hipster shirts

Hipster humor is often sly and biting. They’re a sarcastic bunch for sure. Celebrate your inner snarkiness with a hipster T-shirt adorned with a funny phrase.

The key here is smart and silly instead of rude and obscene. Avoid shirts with swear words or vulgar messages. Instead, choose something sure to elicit a dry chuckle from the other hipsters in the room.

There are two types of people. 1. Those who can extrapolate from incomplete data.” It’s a shirt that’ll have folks chuckling a minute or so after reading. Another funny option is the “I’m silently correcting your grammar” T-shirt. It’s perfect for literary hipsters.

Mens Silently Correcting Your Grammar Funny T Shirt Nerdy Sarcastic Tee Graphic (Heather Black) - M
  • SUPERIOR DESIGN: Crazy Dog T-shirt branded tees are designed and printed in the USA. We screen print our graphic tees with state of the art equipment to ensure vibrant colors...
  • NEW FAVORITE SHIRT: We have our tees manufactured to be the best super soft high quality shirts. Our vintage lightweight fitted tees are made from ringspun cotton to get that...
  • SATISFACTION GUARANTEED: Whether you're cute and adorable or sarcastic and nerdy, get ready to have fun with this graphic tee. Machine washable (wash/iron inside out in cold...

Thrift Store T-Shirts

hipster shirts

Hipsters buy their shirts in two places. They either spend a fortune buying designer shirts directly from the brand, or they search for shirts inside thrift stores.

Buying high-end clothing is easier, but also more expensive. Plus, finding an awesome shirt in a thrift store feels like uncovering a secret treasure.

Also, thrift store gear is considered more authentic. After all, would you rather have a shirt made this year with a retro design or one made in the 1950s? Of course, any self-respecting hipster would wear the older shirt with pride, knowing how difficult it is to obtain.

Finding an awesome shirt at a thrift store does requires some effort on your part. You’ll need to visit thrift stores frequently. Ideally, you want to figure out when new clothes hit the shelves so that you can beat other hipsters to the good stuff. Be prepared to spend some time searching through every section, too, as thrift store organization is typically haphazard.

Final Word

Hipster style doesn’t quite get the respect it’s due. By taking diverse elements from a variety of sources, hipsters created a style all their own, which eventually influenced street style, pop culture, and more.

Although hipster fashions can certainly embrace the eccentric, the underlying style is a calculated cool which fits in at the office and out on the town. From plaid to printed tees and more, the items on our list are a hip way to update your wardrobe and showcase your style.

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