How to Dress Like a Hipster: 5 Ways to Bolster Your Hipster Style

By James Smith

Posted 4 years agoGROWTH

Recently, some internet writers and bashing hipster lifestyle. But not me!

No, I’m part of a small group of more “evolved” writers who not only love and appreciate the hipster lifestyle, but envy it as well. And, as with anything that is evolved, we’re based totally around hate, have a shaky foundation, and have affection for the one thing most people hate.

hipster 1

Man’s #1 enemy…OTHER HUMANS!!!

So in accordance with my membership to this group, which we call the Society of Alone and Tired Internet and Reality Educators, I have decided to help out the Hipster Nation with an article giving you great ways to bolster your hipster wardrobe. Heck! Maybe I’ll even give you 5 of them!!!

5. Start With The Basics

As with any wardrobe, in order to create you’re hipster wardrobe you should just stick to the basics. Hipsters often wear clothes that other people have stopped wearing for decades now. Of course, some uninformed people might say that this is just an obvious and vain call for attention. But not our “evolved” group! We know that, by dressing in clothes no one else wears, it’s easy for your roommate to find you in the case of a stampede of stock photo models.


Good luck finding your buddy in here you unintelligent hacks.

Thus, to begin your hipster wardrobe you need to wear what people wore in the 80’s and 90’s. Typically, our goal is to inspire fear and intimidation into our enemies. Not so that they don’t attack us, but so we can RULE THEM WITH AN IRON FIST!!!


James, I don’t think we can talk about this anymore.- Wingman Legal Team

I’d recommend going with a greaser look, mostly because that one book was amazing. (even though the movie sucked.)

Clothing Items: White T-Shirt, Blue Jeans

Price: $5-$100 depending if you shop Thrift Store or AE.


There are great online clothing shops like, with a range of character clothing. It’s hip, it’s funky and they are always adding new collections. When wearing hipster clothing, my favorite is black and anything is in the darker colors. What’s that famous saying? When is doubt, always wear black!

How to Dress Like a Hipster

Hipster level: Noob

4. Now, Spice It Up Depending On Your Location

Now’s the part where you get to express your individuality by looking like every other hipster in your area. Of course, some people trying to hinder human kind’s advancement might say that this isn’t individuality at all. But we know better, we know that by dressing like everyone else, we’ll know who to fight for when the stock photo people attack.

A flannel shirt is a hipster essential but you need to accessorize based on your own location. If you live on the west coast then I would suggest a nice handle bar mustache and some thick rimmed glasses. If you’re in the Midwest then a stocking cap and some more glasses. If you live on the east coast then a leather jacket and stocking cap are a must, and of course…

How to Dress Like a Hipster

Bow to your new God heathens!!

Since I live in the Midwest, I’ll stick to that wardrobe for the purposes of this article. Price: $25-$120

Clothes: Flannel shirt, Thick-Rimmed Glasses.

 How to Dress Like a Hipster

Hipster Level: Wannabe

3. Facial Hair Is An Absolute Must

Facial Hair on hipsters is like a foam heart in your coffee. Some poor, uninformed soul who is deserving of our pity might suggest that it’s a useless feature and an exercise in excess in vanity. But we at the Society of Alone and Tired Internet and Reality Educators know that both foam hearts and facial hair are a way to show the world that you don’t care what they think, and that you are your own individual.

hipster style

Also, a foam heart just looks fuckin’ awesome.

Now your particular choice of facial hair is up to you. If you wanted to look like a “OG” Hipster you choose the handlebar mustache.

An oldie but a goodie

If you wanted to look tough you could go with a Van Dyke.

Fear my power!

If you wanted to look a little new age you could always go with a goatee or long beard. Or try some other weird men’s fashion trends.


Or you could go with something never soon before…

hipster 13

Uhh…maybe just stick to one of the ones above…


STYLES: Listed above.

How to Dress Like a Hipster

Hipster Level: Enthusiastic “Meh”.

2. Finally, Get Some Sweet Kicks

Finally, if you really want to kick your hipster wardrobe into high gear you need to get the right footwear. Now, some unenlightened commenter might suggest that footwear doesn’t actually matter because no one even looks at your feet that much, but we here at the Society of

Alone and Tired Internet and Reality Educators know better, we know that with the right kicks you will be granted magical powers and if you grab the perfect footwear you will not only be granted magical powers but be able to RULE THE WORLD!!!!


James! We talked about this! No more talk about world domination. – Wingman Legal Team

The best way to do this is to grab your favorite pair of combat boots. Black, if you can. This will not only make your enemies fear you, but also allow you to…

Don’t you say it!!


Price: $20-$50

Item: Black Combat Boots

How to Dress Like a Hipster

Hipster Level: God.

1. When In doubt, Just Follow My Lead

Listen, I understand that follow all these rules and guidelines might be a little tough. So I’m just going to clue you into a little trick into helping follow them. As with anything in life, if you’re having trouble, just follow me!

As a contributing member to the Society of Alone and Tired Internet and Reality Educators (or as we like to call ourselves the SoAaTIaRE.) I’ve dedicated my life to following the hipster way. Why just a look at me will clue you into the whole article. Here’s a picture of me from just a few months ago…

Look at that Swift fellow!!!!

Now go out and…


TOTAL PRICE: $53-$310

TOTAL EFFET: You’ll be looking like a hipster in no time and…ah fuck it, YOU WILL HAVE THE WORLD IN THE PALM OF YOUR HAND!! HAHAHAHAHA!

About the author James Smith

When he's not focused on world domination you can reach James at Facebook. He’s also on and you can go and bother him there too.

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