25 Hipster Outfit Ideas for Men & Style Tips

Hipsters have a keen eye for art, indie-rock music, and any product of creative and independent thinking. This style features various fashion statements that are both unique and pleasing to the naked eye.

And there’s really no judgment when rocking hipster outfits as it’s the point of it all. As a hippie, you channel a free-spirited and liberated sense of self. However, there are some tips to consider to avoid looking like you’re lost in another dimension.

Say what you want about hipsters, but their fashion sense is definitely a must-try this season. They might have lost their sheen for quite a while, but they are back at it again, with something new to offer.

Hipster Outfit Ideas

First off, a real hipster steers clear of anything ”mainstream,” meaning you should travel the road less taken.

Start with crossing branded clothes off your list as it’s contradictory to this style. You might also want to consider the following pointers:

In a nutshell, hipster fashion involves wearing denim, ripped jeans, patterned shirts, beanies, and hats. Basically, any fashion piece with a touch of vintage would meet the cut.

  • Tops. Button-down shirts should preferably be in athletic cuts. And jackets and blazers should be slim-cut.
    From V-neck jumpers to shirts, vests and denim jackets, this fashion is vast. For the smart but casual men, tops such as checked, flannel, or cotton shirts and t-shirts will ooze naturalism and provide a broader and more masculine chest shape.
    T-shirts in this style should ideally have a graphic or band or logo print on them. Add a denim jacket to this for extra volume and a touch of street flair, an all-around accepted garment in the eyes of fashion.
  • Bottoms. As for pants, tapered jeans and slim-cut trousers are your best companions. Trouser styles for the modern male include very well-renowned skinny jeans.
    I would recommend skinny jeans but if they’re not your thing and you prefer a loose fit, why not go for straight-leg jeans with turned-up hems? This will add a natural and carefree flair as well as give you comfort and style.
hipster style outfits for men
  • The Fit. Hipsters love well-fitted clothes, but never too tight nor too baggy.
  • Dressing Up. If you are headed for a slightly more formal occasion, dress up with a slim-cut textured suit, like a tweed blazer, for example. And it wouldn’t be complete without a skinny tie.
  • Hairstyles: Hair should be relaxed and laid back, which means one of the best styles for men in the hipster scene is a clean, scruffy look.
    That does not mean it should not be combed or brushed, but create a casual look. Why not go for a simple but slick quiff? This look shows you can keep well-groomed hair without looking too formal or pretentious.
  • Accessories: You can accessorize your outfit with oversized beanie or other similar casual items. Sunglasses and belts are great accessories for breaking up block colours. Use these to their full potential but make sure colours are flowing and working together. Too much colour contrast will kill an outfit and will stray away from your look.
Fashionable Hipster Outfits for Guys (3)

Where To Buy Hipster Outfits?

Shopping for a hipster outfit may not be that easy compared to getting usual casual outfits, but some garments like jeans, denim jackets, flannels, and old-school sneakers are not hard to find. Start your hunt by having a trip to thrift stores. A friendly disclaimer – you don’t have to get branded clothes as this style defies mainstream culture. These picks are merely examples:

  • BOSS Slim-fit Flannel – $118 on Nordstrom
  • Levi’s Trucker Denim Jacket – $98
  • Quiksilver Cable Knit Beanie – $26.95
  • Smith Slim Sunglasses – $129
  • Converse Chucks – $55
hipster outfits for men


Look Book

25 – Bermuda Shorts

The twenty-first century brought on many trends, and one of them was that boys got a little more freedom in terms of their dressing styles. From Bermuda shorts to colourful jeans to vests being worn as shirts, you name it, and the trend is already there.

These boys show the same kind of freedom, going to play ball a beach party or just another new summer day. Dress up in shorts, or the Bermudas, or simple plain jeans with a graphic shirt. Remember to have your sunglasses and your watches with you. Here are some more ideas for Cool & Stylish Bermuda Shorts Outfits.

Fashionable Hipster Outfits for Guys (8)

24 – For Plus-Size

hipster style outfits for men

23 – Cross Leather Messenger Bag

Get a bag, probably something with a cross strap like a leather messenger bag for a functional look.

How To Dress Like A Hipster  12


22 – Street Style

Back then, academicians and professors only wore these outfits, but today, every man can do it – we owe it to the community. Oxford shirts, khakis, and casual blazers are your essentials for this style.

hipster style outfits for men

21 – Flannel And Jeans

What makes this combo popular is that it’s ideal for both office and after-work errands without having any hint of awkwardness.

hipster style outfits for men

20 – Denim Jacket With Plaid Pants

Two hipster fashion staples in one. They are also both distinct American styles men have loved over the years.

hipster style outfits for men

19 – Iconic Party Look

Aside from having Polaroid cameras and vinyl records, hipsters are known for their iconic house parties. This is a perfect way to rock an outfit like this.

hipster style outfits for men

18 – Denim on Denim

hipster style outfits for men

17 – Knitwear

Hipsters love knitwear like wool sweaters and beanies. Tip: match the colours of the two for a uniform look. Break the dullness by doing some layering, and it’s ideal to do it in fall or winter.

hipster style outfits for men

16 – Biker Jacket

hipster style outfits for men

15 – Retro Shirt And Relaxed-Fit Jeans

hipster style outfits for men


14 – Vintage Shirt

hipster style outfits for men


13 – Tie-Dye Puffer Jacket

Incorporating hipster-style staples in one outfit is a good idea to stand out. For instance, a pink retro-inspired tee worn underneath a tie-dye puffer jacket will provide some pop of color to your statement. Ripped jeans would add the right vibe to your overall ensemble.

hipster style outfits for men


12 – More Flannel

Plaid patterns like flannels look great. Pair a blue flannel shirt with white chinos, and don’t make the mistake of leaving the shirt hanging loose. Finish off with some black leather boots.

hipster style outfits for men


11 – Winter Style

For the winters, just dress up in all black, from your skinny jeans to your black sweater, and a statement black leather jacket as an accessory goes with an infinity scarf or a beanie. What is your thing? Gloves will make you look extra cool with a pair of black army boots.

most stylish hipster men (1)

10 – Teen Guy

Another look for the autumn season is a bit beige and different shades of the same colour palette.

Faded orange jeans and a beige shearling jacket, and a light denim shirt underneath should be your thing as it will give you a boost among your fellows.

most stylish hipster men (2)
most stylish hipster men (3)

9 – Celebrities Style

most stylish hipster men (4)

8 – Autumn Vibes

A very casual and spring dress-up for any fun-loving guy. T-shirt with rolled-up sleeves and a jacket in hand for the cold or jacket over your shirt with sleeves pulled up to show off your accessories.

most stylish hipster men (5)
hipster style outfits for men

7 – Spring Outfit

Also, check  20 Trendy spring casual outfit combinations for men.

Fashionable Hipster Outfits for Guys (4)
hipster style outfits for men

6 – Denim Shorts

A warm climate such as summer calls for an outfit with fewer garments, but that doesn’t mean you can’t be creative by making some changes. To do this, opt for floral patterns and some shorts made of lightweight and breathable materials.

Also, you can save some money by doing some DIY work. For instance, if you have skinny jeans in your wardrobe, cut them off to become a pair of shorts, which are ideal for summer. 

hipster style outfits for men

5 – Blogger Style

Fashionable Hipster Outfits for Guys (9)
hipster style outfits for men
Fashionable Hipster Outfits for Guys (7)
hipster style outfits for men

4 – Beanie With Leather Jacket

hipster style outfits for men

3 – London Look

Every country brings a little different aspect to the styling of the same definition. Now denim over ripped denim jeans and a black leather jacket with a beige shoulder bag is the thing in London for the hipster culture. Grey beanie looks ultra-cool with a pair of brown boots.

Fashionable Hipster Outfits for Guys (13)

2 – Shades of Brown

Hipster with geeks is quite famous and as you can see it is a unique style that incorporates cardigans and sweaters over a button-down white shirt and black pants. Beanies for the extra style points and boots are the same for men as heels for women.

hipster style outfits for men

1 – Checkered Shirt

hipster style outfits for men

Frequently Asked Questions

Q. What shoes should a hipster wear?

A. It’s essential to have several pairs of shoes in your arsenal, as mixing and matching would do the trick for a hippie look. Slip-ons, skateboarding shoes, and leather loafers are all considered good footwear options. Old Converse designs, like Chucks, are also ideal, as well as Reeboks, Vans, and Adidas Originals. For winter and fall, get a pair of Chukka boots.

Q. What accessories should a hipster have?

A. They say bandanas are like a trademark. But no fashion piece can make you look more hipster than a pair of thick-framed glasses, and black rims are a classic option. Alternatively, retro or vintage-inspired sunglasses would work as well. Men also like slim leather belts or colorful ones. As for watches, antique and digital wristwatches are your best bet. For chilly weather, time to grab that knitted and chunky scarf you’ve been dying to rock. Here are some Retro Outfits For Men that you might like.


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