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What is a Hipster? Hipster Fashion Explained to the Mainstream

read about hipster fashion

by Tina Boomerina (Christina Gregoire)

I am going to try to explain hipsters and hipster fashion to you using mainstream American English, even though it’s a massively difficult undertaking and no one else has been able to adequately define the term so far. Hey, I am not a hipster. But, I am a hipster… if you use the classical definition, “One who is exceptionally aware of or interested in the latest trends and tastes.” But that's a stupid thing to say because it makes me sound like a total dork.

And... I know better than to say I’m a hipster, because I am a hipster.

read about the beginnings of hipster fashion for men & women

Mainstream Hipster Dude in Shorts

No, I don’t live on the hipster side of town, but I’m from Seattle, so I kinda know a little about the look… and I think I can explain the torn-jean-vintage-plaid-band-T-shirt-shredded-shorts-retro-peter-pan-dress-mixed-print-tattooed-pierced-plugged-colored-hair hipster style in my own undeck way, as long as I don’t add any wit or sarcasm. If I try to fill this article with humor, my small and limited definition of hipster might become an exercise in esoteric futility… like the rest of my life.

Warning: Don’t Call People Hipsters:

First of all, after you understand a little about the hipster style, don’t go up to some girl or guy and say, “Gee. You’re such a cute little hipster. Can my friend take a picture of me standing next to you in your native element (Capitol Hill or Ballard or Portland or London), so we can show all our friends back in Kansas?”

Hipster is often used as a derogatory term (in Seattle and possibly wherever you are). Well, I don’t know if it’s always been thus, but calling someone a hipster these days can be a slam in some cities. However... even if you say you're NOT a hipster, if you’re into trendy fashion, you’ve probably incorporated quite a bit of hipster style into your wardrobe, whether you know it or not.

What is a Hipster?

A hipster is someone who lives the nontraditional, countercultural, indie life of a hipster.

But, what the heck is a hipster? Well... the answer is complicated.

The best hipster definition I’ve read so far is something like, “A hipster is anyone more hipster than you.”

Hipster is a Fashion:

But, to make things even more confusing, “hipster” has also become shorthand for explaining a particular fashion style.

So, there are two ways to be a hipster. You can be a hipster by living the indie lifestyle or you can be a hipster by wearing the trendy clothing and accessories worn by "real" hipsters.

Hipster is not a derogatory word when you're talking about fashion. We all know what hipster style is once we've seen it a few times. It's hip... and it's based on clothing that the original hipsters found in thrift stores. You can still find classic hipster items in thrift shops if you're lucky, but most of the best stuff is found online (new) and in the trendiest vintage stores (used) because the good stuff is highly coveted.

I Am/Am Not a Hipster:

I've been around a few hipsters. I have nieces and nephews and indie friends. So I don't want you to think I don't understand hipsters just because I'm older.

Yes, I am too old to fit the hipster mold (and I can’t fit into their skinny jeans), however I understand the genesis of the hipster mindset all too well, because I was an indie bohemian - now called a hippie BEFORE IT WAS COOL to be a hippie, and I had a vinyl of Are You Experienced when The Jimi Hendrix Experience was an obscure band YOU’D NEVER HEARD OF, and I wore bohemian print dresses from India BEFORE ANYONE EVEN KNEW WHAT A BLOCK PRINT WAS… and blah blah blah etc. etc.

That was supposed to be funny... but it's not, so I stayed true to my word.

can't be a hipster without these

Hipster Glasses & Fedora

So, I totally get the hipster ethos due to my own teenage rebellion against the mundane mainstream mindset. (Note: I stopped watching TV and listening to mainstream music in the late 60s before you little hipsters were born… so don’t try to out-hipster me just because I don’t know what kind of tennis shoes are fashionable and you do. I try to create fashion trends, not follow them.)

My Indie Credentials:

I am currently a mall-hating (although I like online stores in the UK and a few others), subtitle-loving, anti-suburbanite woman stuck in the suburbs, so I freely admit to being an outcast… even though I once lived a secret life as a Brownie Mom, mimicking mainstream customs by joining the PTA and ferrying soccer kids to games in my Landcruiser. (I love my children, but it was hard to fit in.)

hipster with bad attitude

Ironic Hipster

I understand that the powerful elite (of all persuasions) want to control us through television reality shows, mainstream music, and hustling cable newscasters. I totally get the reasons why anyone hip to the mainstream game would want to find an alternate path.

And, that’s exactly where this story is heading. From what I’ve read, the original hipsters were highly intelligent, highly educated young people who decided to opt out of the preprogrammed American Dream of conspicuous consumption and predefined goals. In other words, the hipsters dropped out and made it hip to be different.

For Mainstream People:

There is nothing wrong with being different.

Constantly growing and changing and evolving is good. Hipsters should be cherished, not mocked. If I were in my 20s, I would have been one... so you'll have to get by me before you make fun of anyone who is unique and artsy and looking towards the universe, rather than the TV, for the meaning of life.

Hipster Fashion Begins:

Well, whatever the reason, hipsters decided they didn’t want to buy into the mainstream lifestyle they had been force-fed throughout their youth. (Sounds normal to me.)

And, although I didn’t know there was an actual taxonomic classification for the tattooed and pierced indie kids who were blooming all around me, and I just thought their intriguing fashions and extravagantly colored haircuts were an esthetic outgrowth of Goth or Punk, I guess I was surrounded by hipsters… about fifteen years ago… without even knowing it.

read about hipsters

Hipster Style Suit

However, I didn’t think about those tattooed kids all that much. I’m an artist. I love people who live outside the box. Indie is normal to me.

And, I just assumed that ink was an urban tribal thing... a way to flash one's calling card to other like-minded people.

Vintage Thrift Store Fashion:

Well, a lot of the clothing those tatooed kids wore was stuff that came from thrift stores. Nope, I didn’t think about it at the time because I didn’t go shopping with random strangers.

So, I don’t really know if those hipsters bought secondhand clothing because it was cheap, because it was anti-mainstream, because it was anti-label, because it was a form of recycling, or because some guy woke up one day and decided he wanted to look like James Dean… and everyone else followed. You tell me. I wasn’t there.

I do know that a lot of men started dressing in homage to the beat generation… with a few additional tattoos and a few fewer berets. And, a lot of women started wearing tight-waisted, good-girl dresses with little buttons and frilly Peter Pan collars… the kinds of dresses that used to make me puke in the 60s… but somehow didn’t seem so square anymore when worn with stark black hair and stark black tats.

And, I started liking those retro dresses that I had hated in high school. And THAT was a strange phenomenon.

Hipsters Can Be Smug:

I didn’t know that hipsters thought they were better than the mainstream, but I did know it. Of course, there wasn’t a lot of social interaction between the hipsters and me (age related), however I sensed that hipsters were not “outside” the mainstream, but rather "ahead" of it… or "above" it. Well, I suppose I intuitively knew they were laughing at conventional culture… just as I had laughed when I first realized I might be happier if I stopped trying to conform to the normal, mainstream, Suzie-Homemaker, bouncy-cheerleader persona that was expected of me during my formative years.

Hipsters, Hipsters, Hipsters

I’m rambling, but I’m not rambling. It’s important to understand the idea behind the hipsters, because what's hipster today may not be hipster tomorrow.

That’s because hipsters have a general disdain for mainstream sensibilities. Once the hipsters find out their latest, hip, edgy trend has been abducted and adopted en masse by the bourgeoisie, it will no longer be cutting-edge.

read about hipsters and hipster fashion

Little Hipster Dude

And, the avant-garde have reputations to uphold. Therefore, a true hipster will always be on the lookout for something newer and better... just like any artist.

So, why do you care? Well, it means that the hippest hipster fashion may soon be something else… and the hottest thrift-inspired ensembles (of this very moment) could morph into a simpering polyester collection at Wallymart.

But, the Wallymart outpourings (in adult sizes) usually take about five years to materialize… so you should consider embracing more of the current hipster trend, because most of it isn’t even on the radar in Middle America... and hipster is here to stay... for as long as it stays.

What Exactly Is This Crazy Hipster Fashion People Keep Talking About?

Okay. You’ve heard enough about the genesis of the hipster tribe to get a general understanding of the hipster mindset. So… let’s talk about artsy hipster clothing.

This “new” fashion trend makes sense when you understand that the hipster look is all about artfully combining vintage clothing in a new, meticulously casual way that’s formulated to mock the traditional consumerist lifestyle.

(Article Continues)

If you continue reading, you'll find a partial list of what to look for in the vintage department of your friendly neighborhood thrift store... if it hasn't already been wiped out by trendy teenyboppers and underground hipsters.

Click to keep reading and to find out exactly what hipsters wear according to the current paradigm.

Photo credits page 2.

Tina Boomerina (AKA Christina Gregoire) is a Baby Boomer born at the end of 1952. Her mission is to make the internet a kinder and gentler place for Baby Boomer women around the world. Tina's specialty is fashion for women over 50.

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  1. Ray AKA Mr Boomerina

    Yes love I am a hipster glad to see you finally realized how cool I really am. The rest of the world will follow me.

    • Tina-Boomerina

      Ray, I think you need more accessories (and layers) to qualify, but if you come over here, I'll pierce your nose with a pair of scissors and help you on your merry hipster path. If that's not enough, I'll tattoo your neck with ink and a razor blade. What are some tribal symbols of New Hampshire?


  2. troutay

    I am not a hipster. I am just me. sometimes I find something good at the thrift store like a yellow man's sweater.
    or sometimes I just add something odd to my wardrobe because it amuses me. While I do not dress quite like my
    mother or grandmother did at my age, there are some benefits to second hand clothing. If it has lasted this long and looks rather well, then it works.

    • Tina-Boomerina


      You sound like an indie... are you sure you're not a hipster? hahaha You may be a hipster posing as a mainstream chick. I may make you buy some Wayfarers and move to London.


      • Tina-Boomerina

        Hey, if you don't know my sense of humour, you may not know that I'm kidding. However, the part about moving to London sounds like something you would like. I know I would.


  3. troutay

    I would visit, but I don't like damp weather. Besides, we are cousins, remember? Your last name is my grandmother's last name.

    and I think you have a great sense of humor

  4. troutay

    Tried to respond but it didn't go through.
    You have a great sense of humour. Although I don't like damper climates, it would be fun to visit.
    Besides, I think I told you before that you have the same last name as my grandmother, so we must be

    • Tina-Boomerina


      I've had it up to here with damper climates. I'm okay with Seattle if I can spend the winters in Hawaii, but I think I need a new climate. I just can't find a place that my husband and I both like. He likes Phoenix. It reminds me too much of Los Angeles. We're still looking.

      I remember you now. I tried to find a relative with the last name and my husband didn't know any. I can make a guess but I can't remember the first name of your Gregoire. I've only been a Gregoire for 10 years as this is my third husband... so I wouldn't know any Gregoire's that I haven't met.


  5. troutay

    I would settle for Arizona in the winter any time. there is so much to see and do. We usually go out to visit
    family there and it is such a nice change from our Minnesota winters. However, the heat in the summer is awful
    but never as bad as the steamy heat in Florida. But, we have the best of two worlds as we built a small summer
    cabin near lakes north of the Mpls/St paul area. So in summer we can stay cool and in winter, we can visit

    Gregoire. Her first name was Florida or as we called her "Flora". She grew up some place outside of

  6. troutay

    I think she was an illegal immigrant to the U.S from Canada. From the stories I have heard she actually had two birth certificates. The local priest in Wisconsin wanted to marry her to someone in the U.S. So a few things were fudged. This is just family history mind you, I don't really know for sure.

  7. Cherie

    Hipster look l ike hippies

  8. judi

    I think I was hipster before there were hipsters, but I was just trying to be unique... wearing a Navy officer dress coat, Army fatigues, my mom's Pendleton wool and my dad's zip up cardigan in the 80s. Fast approaching 50, I still wear the pieces that fit, my dad's sweater is older than me but made of Orlon it is still going strong.
    The saddest thing is that it has to be tagged and copied, sometimes it is just personal style or wearing something that reminds you of some one you love. I know I was always trying for a connection to my family, and then it became - I just gotta be me!

  9. krispiemae

    I'm not quite a boomer, I'm more of a gen-xer, but I feel you on living in the 'burbs and not fitting in. I married late, to a younger man, and started my family late. People with kids my kids age are so much younger and people my age are starting to be grandparents. I have always been "interesting" and have led a non-traditional life, so I really don't have a lot in common with...anyone. Honestly, I'm lonely. Sometimes I even wish I was more conventional, but that just isn't possible for me, and I can't seem to just "pretend". Any advice?

    • Tina-Boomerina


      I hear ya, babe. How did we end up here?

      I'm not sure what kind of advice I can give you and some of it depends on where you live.


      Most advice-givers just say you have to "thrive where you're planted" as if you're a freaking geranium or tomato, but I know better. You need the right mix of water, nutrients, and fertilizer to thrive.


      Well, if you have kids, you have to do what's best for them and that probably means sticking it out in the burbs for a while... unless you have other options you're not mentioning.

      And, you can be "yourself" to a point, when you live in the boring burbs, but you don't want to embarrass your kids too much if they're teenagers. However... you're never going to fit in. Accept it. Deal with it as best you can.

      I finally gave up on suburbia and talked my husband into moving to a small-ish town in Oregon. ... Well, we tried to move to the actual city of Seattle... but it was way out of our price range. So, after looking around, my husband decided this whole area was just way too expensive. So, I get to move to Bend Oregon! It's a place I picked! I think Bend will be better than suburbia... anything is better than suburbia.

      The people in the suburbs are robots. They can't think for themselves. They do everything exactly the same as their neighbors do. God, just shoot me.

      So... my advice is to move to Bend, Oregon.


      I know that's not an option... My real advice is to take some artsy classes... especially any art classes that mention words like "experimental" or "unleashing your creative side". Try a class in hat-making... or clothing design, glass blowing, entrepreneurial start-up help, using the right, side of the brain, tattoo design... just avoid craft classes. Too churchy, boring.

      Art classes might not attract the people you want, but there's a slim chance you will run across a "real" artist who wants to paint something other than traditional watercolor flowers. Look at your local college's continuing education section or craigslist. Other classes where unique people might congregate are things like astrology (doesn't matter if you believe), near death experiences, psychic abilities... Just be prepared to weed out the true crazies. Don't give everyone your home phone or address until you know they're not wacked. But, most people in alternative classes are a lot like yourself. I've tried a few.


      Once your kids are grown you might be able to move someplace with more vibrancy.


      I'm starting a forum.

      Once I get settled in my new digs, I am going to be working harder to get my forum rolling. I'll set up a section for women trapped in the suburbs... I'll put a link below once I start it. A forum is not a replacement for a real life, but it's better than nothing.


      It's very difficult to find real friends once you're out of college. It just is. Stop watching Sex and the City or Friends. It's just bullshit. It will make you feel sad. Producers have to PAY those women to act like they are friends (in movies, on TV). Bullshit bullshit bullshit.

      KM, I wish I knew better answers. It sucks to have people around you who are the wrong age. Sometimes, their age doesn't matter. But.... most of the time they don't get your jokes... or your ideas.... or your point of reference. So, go to the mall and cry. Life sucks for you right now... but hang in there because it will get better.

      If you live in Central Oregon, let me know. We can go to the local mall and dance on the tables to scare the normal people. But, I'm very weird according to my husband... so you do this at your own peril. hahaha.

      Maybe other women have better suggestions. I'm sorry to hear your plight. Maybe you could write an article for me (anonymously or not) about how much you hate the suburbs. You could just list the things you hate and list what you wish you had. I know you're not alone. Your article might attract comments with suggestions for living with your sad situation.

      Consolation prize: In my opinion, people who hate the suburbs are generally more intelligent than people who love the burbs.

      Tina Boomerina

      • krispiemae

        Thank you so much for the wonderful reply. Eventually we will get out, back to the rural homestead I came from (Only child / ageing mother). Out there people just don't care how weird you are. I've come home at 6am in a crotch length, shiny silver disco dress and run barefoot down the hill screaming at the top of my lungs to chase the cows out of my garden and the neighbors still like me. I really shouldn't complain, I'm in Columbus OH, a fairly young and progressive town. I'm just older than that crowd and have toddlers, kinda puts a damper on my nightlife. Even when I do get a sitter the next day is a killer. Two-year old's don't understand hangovers.
        My husband is a drummer in not one, not two, but three bands. He works two jobs and is building a recording studio. There are bands in and out of our house all the time. You would think I would get to do cool stuff and meet cool people but it doesn't work out that way. I can barely get to the grocery store! let alone get to do anything I HATE exercising but am seriously thinking about joining the Y for the free childcare. I guess with really good music I could walk on a treadmill for a hour or two. I had lots of friends in high school and in my twenties, even most of my thirties but we all went our own direction and got caught up in our own lives. Other than Facebook I only see them a couple times a year...and we are all so busy (or in my case tired). With no life to speak of I have nothing to talk about even when I do talk to other adults. My husband thinks I should get a job but with his schedule and the cost of childcare it isn't really a possibly. I'm just in the isolating years of motherhood and without my kind/age of mothers around it is even worse. Plus my pink hair and tattoos scare away all the (much younger) suburban mothers at the park. They all care so much about what people think of them that they are all the same so they all get along, at least to each other's faces. I love my kids so much and spending their childhood with them is a priority for me it is just a lonely time. I guess it probably is for most mothers no matter what their age. Thanks for the advice, eventually I will move back where I came from and at least then I will have my family. By now they are used to my special kind of crazy. ;)

        • Tina-Boomerina


          Pink hair, tattoos and a silver disco dress. You should move to my new neighborhood in Bend, Oregon. (I'm not there. Have to wait for the current residents to move out... but we bought the house.) We need you in Bend. I need you in Bend.

          Wish this country had more people like you... and your hubster. You sound wonderful!