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

hipster outfits

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 Authentics Men's Long Sleeve Quilted Lined Flannel Shirt Jacket, Biking Red Tri Color Buffalo, Large
  • RELAXED FIT. Constructed with comfort in mind, this long sleeve quilted lined flannel shirt is a wardrobe essential for those cold Winter nights.
  • HEAVYWEIGHT MATERIALS. Built with button cuffs and quilted polyester padding for more durability and added warmth.
  • FOR ADDED WARMTH. Padded with diamond black quilted polyester to create extra warmth while also creating breathability, this is an extremely versatile flannel shirt.
  • FUNCTIONAL STYLE. Lined with 100% cotton, this brushed flannel is made with style in mind. Wear it on the job or out to lunch, this essential closet staple can be worn for many occasions.
  • ADDED STORAGE: Constructed with (2) dual front chest pockets and (2) side seam pockets, this flannel has easy-access storage for all your basic necessities.

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.

New Republic Men's Chuck Suede Chelsea Boot with Crepe Outsole - Sand (9)
  • CLASSIC STYLE: Refined chelsea boot silhouette with an elastic gusset and pull tab for easy wear
  • DETAILED CRAFTSMANSHIP: Upper made with high quality cowhide suede leather
  • ALL-DAY COMFORT: Natural crepe outsole and padded insole for extra comfort
  • UNMATCHED QUALITY: 100% Leather lining and footbed for breathability

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

hipster outfits

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.

Men's Premium Casual One Button Slim Fit Blazer Suit Jacket (3625 Grey, M)
  • Material --- Polyester&Cotton; Dry Clean Only(Recommended); Hand washes max temperature 40°C, Do not bleach, Iron max 110°C.
  • Suit blazer design --- Modern fashion Lightweight Suit Jacket Blazer with notch lapel, one button closure, left chest fake pocket decoration, two front flap real pockets, Inside a real pocket.
  • Casual and great looking --- Finished by excellent stitching, the stylish blazer has a linen texture specially designed for western men, will really make you minimalistic, elegant, and generous and in the crowd.
  • Recommended pairing --- Match with a white dress shirt, khaki pants or jeans and a pair of casual shoes maximum help improve your public image and leave an unforgettable impression on people around you then.
  • Occassions: Great for casual, Formal, Business wear and other special events

Big City Rockstar Style

hipster outfits

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.

AOWOFS Men's Faux Leather Jacket Double Belt Punk Motorcycle Zip Slim Fit Black
  • Fashion Slim Fit Style Turn Down Lapel Motorcycle Biker Faux Leather Jacket
  • Double waist belt design with buckles, Stand collar with throat belt buckles.
  • Two waist zipper pockets, one chest slanted pocket, one with a stud button flap design pocket.
  • High quality material, soft and comfortable wearing. Winter warm Outdoor overcoat.
  • First scrub with a damp cloth, or wash away with a special cleaning agent carefully and hanging dry .If the jacket surface gets wrinkled, you can iron it briefly at a moderate temparature by using an old towel.

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

hipster outfits

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 Genuine Leather Suspenders For Men with Elastic Strap & Dual Clips (Tan)
  • PREMIUM QUALITY TAN LEATHER SUSPENDERS – These very classy leather suspenders for men are the ideal accessory for a casual, put-together look. We love our suspenders for men paired with skinny black jeans and a relaxed white shirt or tee. These Y back styled suspenders feature button attachments, high quality hardware and genuine leather detailing; ensuring they remain a staple in your wardrobe for years to come!
  • VERSATILITY – Our premium quality Y back mens suspenders are incredibly versatile. These cognac color clip suspenders can be worn with formal attire for work or a wedding, or paired with jeans and a shirt for more casual attire. The genuine leather detailing and gold hardware gives them a polished touch, while the suspender clips make for easy, comfortable wear.
  • DESIGNED FOR COMFORT – Our adjustable strap clip suspenders are made with a Y back design and soft elastic back strap, allowing for extra comfort and mobility while preventing clips from slipping off you pants when sitting or kneeling. JJ suspenders are designed in NYC combining over 20 years of experience creating high quality clip and button suspenders for men. All our clip on suspenders are handmade to provide the perfect look and fit.
  • FEATURES – Our tan mens leather suspenders are designed for heights between 5’8 and 6’3 but fit may vary depending on body type and torso length. Return for full refund if fit isn't perfect. These genuine leather Y back suspenders have both dual clip attachments as well as button attachments. The suspender straps are 3/4” wide and feature the classic Y back design with genuine leather detailing. One size fits all.
  • LEATHER BRACES: GIFT SET FOR MEN – The JJ Suspenders Y back genuine leather skinny suspenders make a perfect gift for any occasion. They come in a super stylish burlap tote bag with other accessories included; such as a mini sewing kit, extra buttons for pants and extra suspender clips. Our premium quality mens suspenders are very classy and make for a great gift idea for any gentleman.

Beach Ready Summer Style

hipster outfits

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.

Sale
Haola Women's Juniors Vintage Denim High Waisted Folded Hem Jeans Shorts Light Blue M
  • Available In Regular Size, Pls Choose The Size As You Usually Wear (Note:The Generic Amazon Size Chart Is Not Our Size)
  • Material: Demin, 100% Cotton - Stretchy
  • Waist Type :High Waist Types :Shorts Color :Blue Material :Denim Style:Fashion Fit Type
  • Hand Wash/Machine Wash
  • Measurements: Small: Waist: 26", Hips: 34", Thigh:21 ", Length: 14" Medium: Waist: 28",Hips: 36", Thigh: 22", Length: 15" Large: Waist: 30", Hips: 38", Thigh: 23", Length: 16" X-Large: Waist: 32", Hips: 40", Thigh: 24", Length: 17" XX-Large: Waist: 34", Hips: 42", Thigh: 25", Length: 24"

Skate or Die

hipster outfits

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.

Sale
Vibrant Women's Juniors High Rise Jeans w Heavy Distressing Black 1
  • High waisted skinnys with a super stretchy jegging feel. Heavy with distressing withÊholes on the thighs and distressing at the ankles.ÊFront and back pocketÊÊwith a zip fly and button closure.
  • Machine Wash Cold
  • High quality construction MADE IN USA
  • 39"/99 cm Top to Bottom 27.5"/70cm Inseam - MeasuredÊ on a size 7 (Model is 5'5/wearing size 3)
  • Vibrant Sizing Info: 1=24, 3=25, 5=26, 7=27, 9=28, 11=29, 13=30, 15=31

A Cool Outfit for the Chilly Fall

hipster outfits

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 Classic Warm Winter Hats Knit Cuff Beanie Cap Daily Beanie Hat Skullies for Men Women Golden
  • Own Exquisite Style - The beanie is with exclusive double turned up brim. It is a cuff beanie, but also become slightly shorter fisherman’s style beanie.when you turn up the brim again, unique and elegant!
  • Get Comfortable Fit - Premium cotton yarn with spandex makes a comfortable fitting beanie.
  • Embrace Premium Cotton - Crafted from superior cotton yarn, this beanie makes for a comfortable, soft hat that goes with anything.
  • Take Perfect Companion - Nice to have during the in-between-seasons-kind-of-weather. We also like to refer to it as a "city beanie", can wear anytime and anywhere, indoor or outdoor.
  • Enjoy ZOWYA quality and service - Please click "ZOWYA" sign to find our more collection on Amazon. ZOWYA - Forever For You!

Layers on Layers

hipster outfits

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.

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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