8 Hipster-Approved Outfit Ideas

For years, hipsters were considered the tastemakers of style and fashion. But, as the hipster movement reached its boiling point in the early aughts, and hipsters started to look like they were coming off an assembly line, the idea of being a hipster lost some of its luster. In fact, the word hipster alone began to take on the connotation of a four-letter word.

Say what you will about hipsters, but one thing is for sure: Hipsters have always had a keen eye for style and design. If you’re looking to inject some new life into your style this year, why not consider adding some hipster swag to your looks?

What is hipster style, exactly? Hipster style can be many different things. It can be gaudy and over the top, or understated and refined. Hipsters love to resurrect trends and styles of the past, and they’re always quick to put a stylish and unconventional spin on even the most simple of outfits. The style is one part trendy, one part tongue-in-cheek, and all parts fun.

Today, we’ll take a closer look at some of the coolest hipster outfits for this season so you can add some much needed cool to your fall styles.

Eight Hipster-Approved Outfits Perfect For This Year

Whether you’re looking for some new threads for the office or some great ideas for what to wear outside of work, there’s something for everyone on our list below.

Denim & Flannel

Two staples of any hipster wardrobe are denim and flannel, and it’s easy to see why. Both denim and flannel are distinctly American styles that we’ve loved for centuries, and they’re just formal enough to keep you looking sharp at the office, and at happy hour when you’re off the clock.

Wrangler Long Sleeve

wrangler authentic men's long sleeve

Constructed with comfort in mind, this long sleeve quilted lined flannel shirt is a wardrobe essential for those cold winter nights. Built with button cuffs and quilted polyester padding for more durability and added warmth.

Those who love denim and flannel have an almost cult-like devotion to these styles, and you won’t have to look far to find artisanally produced versions of each. If there’s one thing hipsters love, it’s anything artisanally made.

Just as important as the look itself is how it fits, so you’ll want to pay special attention to how the clothes fit when you sharp. Hipsters are known for being impeccably tailored. The clothes don’t need to be overly tight, but they should be far from baggy.

To rock this look, pick up a pair of overdyed raw denim with a slim-straight or skinny cut, and pair it with the flannel of your choice. This versatile look matches well with virtually any footwear you choose, especially with a pair of Chelsea boots or worn dress shoes.

Chelsea Boot

new republic men's chuck suede chelsea boot

Refined chelsea boot silhouette with an elastic gusset and pull tab for easy wear. Upper made with high quality cowhide suede leather. Natural crepe outsole and padded insole for extra comfort.

This versatile look is perfect for virtually any setting, primarily if you work in a casual office. One of the reasons why a flannel button-up with jeans is such a popular combo is it can take you from the office to happy hour with ease, keeping you in style and fashionable in the process.

Academic Cool

The hipster set is responsible for keeping the flame alive when it comes to classic American academic style. We’re talking oxford shirts, khakis, and casual blazers, here. For decades, the only people you’d see wearing this look were stuffy professors and other academic types. Thanks to hipsters, what was once considered old and stuffy is now fun and new.

Like the look above, tailoring is essential. Make sure each piece of your outfit is fitted and tailored close to the body. To add some academic cool to your wardrobe, consider pairing a solid color oxford shirt with khakis and a brightly colored fabric belt. Pair this look with a casual blazer, like this one from Beninos to really nail the hip professor aesthetic.

For work or for play, this studious outfit is ideal for any aspiring hipster who is looking to inject some cool into their wardrobe without looking like they were dressed by a teenager.

Casual Suit

beninos men's premium casual suit

Compared with the orthodox suit, it has super matching, younger and more casual. One button design, lightweight suit jacket.

Big City Rockstar Style

One thing that seems to never go out of style, whether we’re talking about hipster outfits or fashion in general, is the rockstar look. This look projects confidence while letting people know that you love fun and don’t take yourself too seriously.

The rockstar look is especially easy to put together. All you’ll need is your favorite band t-shirt, your tightest pair of jeans, and a black leather motorcycle jacket. Make sure that each aspect of your outfit is fitted to achieve maximum rockstar chic.

Leather Jacket

aowofs men's faux leather jacket

High quality material, soft and comfortable wearing. Stylish and lightweight faux leather jacket, suitable for casual daily wear. Two waist zipper pockets, one chest slanted pocket, one with a stud button flap design pocket.

As for footwear, pair your outfit with combat boots, Chelsea boots, or a beat-up pair of dress shoes. From there, add your favorite accessories, like a fresh pair of shades, a bandana, or some bracelets and rings. There’s no wrong way to wear this self-expressive style, so make sure you’re having fun with it.

Dust Bowl Chic

Hipsters have an appreciation for all things vintage, and that extends to fashion as well. It’s not uncommon to see a hipster channeling the Great Depression with their outfit. The key to nailing this look is to give some subtle nods to the past without appearing like you’re a B-list actor in a period piece.

To pull off this look, we’d recommend starting with a pair of slim-fit khakis or chinos. Next, add a button front henley in a natural, muted color. Finish it off with a pair of suspenders and a pair of desert or Chelsea boots, and you’ll be effectively channeling the past without looking like you grew up during the Roosevelt administration.


jj suspenders

These very classy leather suspenders for men are the ideal accessory for a casual, put-together look. We love this suspenders for men paired with skinny black jeans and a relaxed white shirt or tee.

Beach Ready Summer Style

These days, fitted shorts and patterned button-ups are all the rage. But this is a style that hipsters have been nailing for decades. This look comes off as fun and tongue-in-cheek, and you’re sure to look like the most fashionable person marooned on Gilligan’s Island if you take these style cues.

Start with a pair of slim-fit flat-front shorts that hit just above your knee. If your shorts hit a bit too low, a tried-and-true hipster trick is to cuff them a time or two to hit the desired length. Pair that with a casual button-up with a fun print or graphic, and you’re good to go.

Pair this look with a pair of low-profile sneakers like the Vans Authentic or Converse Jack Purcell, and you’ll be summer-ready in no time. This look is perfect for enjoying some R&R in the warmer months.

Jeans Shorts

denim high waisted folded hem jeans shorts

This folded hem jeans shorts is so classical and fashion in spring, summer and autumn! Traditional 5 pockets with button and zip fly closure. Great stretch and soft in the material for a comfortable fit. 

Skate or Die

Skateboarding culture and style have been experiencing a renaissance of sorts over the past few years. However, this style is nothing new for hipsters. The main reason why the style is so fashionable is that hipsters have been rocking it for years.

This style is characterized by t-shirts, ripped jeans, and skate shoes. Add an oversized flannel or hoodie to the mix to complete your outfit during the colder months. As with most hipster-approved styles, you’ll want to opt for a pair of tailored jeans that are cut skinny or slim, like this destroyed pair from Enrica.

Accessorize your outfit with a shoelace belt and DJ-style headphones. This will add an extra bit of swag to your already stylish ‘fit. It's stylish for guys or girls, and it’s a great look for the weekends or casual outings.

High Rise Skinny Jeans

vibrant women's juniors high rise jeans

High waisted skinny with a super stretchy jegging feel. Heavy with distressing with holes on the thighs and distressing at the ankles. Front and back pocket with a zip fly and button closure.

A Cool Outfit for the Chilly Fall

If there’s one thing hipster’s love, it’s a wool knit beanie and a sweater. This outfit checks both boxes, so it’s sure to delight even the most unenthused hipsters.

To nail this look, get a chunky cable knit cardigan and throw it on over a t-shirt or oxford shirt. Next, accessorize with a pair of slim-fit chinos or skinny jeans. Tie everything together with a pair of desert boots, Chelsea boots, or your favorite pair of runners. Keep your head warm with a classic chunky-knit fisherman’s cap, like this beanie from Neff.

This versatile look is perfect for running errands, a day at the office, or even a casual date.

Zowya Fisherman Beanie

zowya fisherman beanie

Premium cotton yarn with Spandex makes it retain the breathability and coziness of cotton while adding the elasticity of Spandex. The breathable material provides a ventilating frame allowing proper regulation of body temperature, which is necessary when exposed to weather on the water.

Layers on Layers

If there’s one thing hipsters love, it’s keeping cozy with lots of different layers. This look is an exercise in layering, and it’s perfect for when the weather can turn on a dime.

For this look, start with your favorite t-shirt or short-sleeve henley, and over that add a casual button-front shirt, and a cardigan or chunky sweater. You can also pair it with jeans or slim-fit chinos, and your favorite shoes or Chelsea boots.

Complete the look with the outerwear of your choice. Bonus points if you wear it with a peacoat or leather jacket. This versatile look is perfect for virtually any setting, from the office to happy hour to everywhere in between.

Casual Shirt

pegeno men's fashion casual shirt

95% cotton, 5% spandex. Soft and comfortable to your skin, suit for daily wear or work. Looking handsome while retaining ease of movement and added comfort.

Final Word

The hipster-approved looks on our list can inject some much-needed style into your fall wardrobe. From rockstar approved styles to more refined and professional styles, you can’t go wrong with these hipster outfits.

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