I Think I Dressed Like A BK Hipster For A Week

Before my transformation, I had a vague idea about Brooklyn hipster style. Living in a small town in England, I couldn't tell you what the average Brooklynite wore, never mind describe the threads of the borough's hippest residents. So, I dressed like a Brooklyn hipster for a week and discovered a whole new style that I’d previously overlooked.

After much time spent on Google Images, I decided that the cast of Girls (a show set in Brooklyn), and in particular, Jessa, would be my main source of inspiration, but I would also refer to my online image research when choosing garments.

Although one should never paint people with the same brush, my findings lead me to a few personal conclusions about the Brooklyn hipster subculture. For one, Brooklyn hipsters like to look cool. They dress in mismatched outfits seemingly compiled from thrift stores or their grandmother’s wardrobes. To me, they seem to be trying to stand out by looking random AF, in the hopes that someone will give them props for their creativity.

Of course, as someone who’s not actually a part of this subculture and being located very far away from Brooklyn, the following style interpretations are my perception of the Brooklyn hipster subculture — which might not be in-line with yours, or in fact, anyone else’s! With all of this in mind, here's what it looked like when I thought I was dressing like a Brooklyn hipster for a week.

Day 1: The Khaki Jumpsuit & The Fedora

Roll Neck Skinny Rib Jumpsuit Khaki, $35.20, / Heidi Ribbon Trim Fedora Hat, $16, / Casual Influence Boot In Cognac By Rocket Dog, $69.99,

For my first day, I imagined what Jessa from Girls would wear. Her style is often OTT, eclectic, random, and relaxed all at once; she looks like she's on her way to an amazing party 24/7 and she's often spotted in a cool hat. So I put on this ribbed jumpsuit with a roll neck because I believed it walked the line between smart and casual. I added the fedora to give it an eccentric vibe and make it slightly more dressy.

As soon as I slithered into this jumpsuit and popped the fedora atop my crown, I felt really out of my comfort zone. Don't get me wrong, I love kooky clothes, but not ones which appear to fall under the umbrella of what I like to call "contrived randomness." My fiancé, who usually describes most things he likes as "alright," said I looked cool, which threw me for a loop. I felt a little like '90s Rachel Green at a cowboy themed restaurant.

However, I was more than pleasantly surprised at how comfortable the jumpsuit was and I really liked the boots. My only issue was, after a road trip to a nearby city, I found my hat very difficult to wear while sitting in the car; the large rim meant I couldn't properly sit back, so I removed it for the majority of the journey.

When I was out and about in my hometown — which is similar to Gilmore Girls' Stars Hollow, in that you can't walk down the street without seeing someone you know — I found myself hiding my face by tilting my head down. Although comfortable, I felt very out of place in my Brooklyn hipster inspired attire in my hometown; I feel folks here likely know little about the Brooklyn hipster trend. I was feeling dubious about the rest of the week.

Day 2: The Gappy Bodysuit & The Silky Trousers

Tab Side Bodysuit Black, $32, / Woven Joggers Sold Out Similar Style, $16, / Boots As Before

On the second day of this experiment, I learned I have an abnormally long torso. This news came to me when I found I couldn't fasten the poppers on my bodysuit. However, all was not lost as you can see — I managed to wear it undone and hide the evidence with the patterned pants. I chose this outfit because it was the weekend and I was having a date night.

I loved how comfy the silky pants were, and the sexy vibe of the happy bodysuit. However, I soon realized that because the bodysuit was undone, it rode upwards when I walked and (because of the side gaps) it appeared I was wearing a giant thong. This was not a good look for me. I think this ensemble epitomized the notion in my mind that hipsters will do almost anything to look quirky, but I couldn't bear it so I changed into my pajamas after I got home.

Day 3: The Ripped Jeans, Plaid Shirt & Pork Pie Hat

Evie Low Rise Basic Black Knee Rip Jeans, $35, / Khloe Brushed Check Shirt Sold Out Similar Style, $26, / Laura Wool Pork Pie Hat Sold Out Similar Style, $16, / Boots As Before

I paired the plaid shirt and skinny jeans together, because this combo reminded me of a trendy singer-songwriter on the way to her next gig; plus, IMO, plaid is the most basic and overused print in the hipster handbook so I wanted to utilize it. In an effort to look quirky and stand out from the crowd, I added the pork pie hat. I was relieved to put on a pair of pants and a plaid shirt, but I felt at odds to my own personal style in the androgynous hat. Again my fiancé approved of my look and even went so far as to say I looked like a contestant for The X Factor.

Being more of a dresses and skirts kind of gal, I forgot how tight skinny jeans were. It wasn't long before I was reminded of my emo period and throughout the day, my legs felt increasingly constricted. I had the epiphany that perhaps I'm not cut out to be a Brooklyn hipster because I value comfort way too much.

Day 4: The Sweater Dress & Shades

A Kindred Sol Sunglasses, $19.99, / All Things Must Past Dress, $59.99, / Boots As Before

Now this was a look I could get behind! On the fourth day of my hip adventure, I took inspo from Girls' Hannah, whose wardrobe seems to have multiple vintage or thrift store finds. I wanted to put a trendier edge on Hannah's haphazard style, so I went for a fall-appropriate, retro style sweater dress with a pair of modern sunglasses that look as if they're from another era. I literally loved everything about it, from the shades to the sweater dress, to the tights and the boots, it was comfortable yet also made me feel stylish. I loved the vintage vibe of the mustard and navy sweater dress and how well it paired with the duck egg blue sunglasses.

We went to feed some local ducks at a nearby duck pond and it was then that it dawned on me that I wasn't dressed appropriately for the occasion. There was mud and grass, plus the weather wasn't the best, so my sunglasses were irrelevant. Sad times.

Day 5: The Slip Dress & The Oversized Cardigan

Dauntless Steps Dress, $59.99, / Julia Cable Pocket Cardigan Sold Out Similar Style, $35, / Boots As Before

My fiancé could not get on board with this outfit. He said that when I removed the cardigan, you could see the outline of not only my nipples, but my entire breasts and more. As someone who supports the #freethenipple movement, I was a little disgruntled at his comments, but when I checked myself out in the mirror, I kind of understood what he meant — the dress clung to everything.

I decided to keep the cardigan on, because sadly, not many folks go bra-less where I live and I felt very self-conscious and naked without it. As an entire outfit, I wasn't keen on the dishevelled granny closet aura it was giving off, but I enjoyed how free and breezy the dress was. I had been trying to emulate Jessa's extravagant, otherworldly style. I wore a pretty shift dress — that would likely be worn as evening attire by most folks — with a chunky cardigan in an attempt to look like I'd been out all night and thrown on a cardigan when I'd arrived home. Basically, I wanted people to feel curious about me and wonder what I'd been up to. Needless to say, my pairing didn't really work.

Day 6: The "Cool" Bodysuit, Butterfly Print Cardigan & High-Waisted Shorts

Flutter You Waiting For? Cardigan, $49.99, / 'I'm Cooler On Instragram' Slogan Bodysuit Grey, $8, / Shorts, Author's Own / Boots As Before

Although Instagram is my favorite social media platform, I felt a little weird about proclaiming to the world that, "I'm Cooler On Instagram" via this bodysuit. But, I decided to wear it because the Brooklyn hipster subculture is mostly a millennial thing and our generation (especially younger millennials) tend to be super into social media. Having said that, I soon forgot about the vain slogan because it was super comfy.

During a trip to my local cinema, which is located in an amusement arcade, I saw a bunch of teens hanging out, frittering their allowance away. I began to feel really old and thought my outfit could easily have been sported by a sixteen-year-old, not a woman nearing thirty. Of course, anyone should wear whatever they feel good in, but this ensemble made me feel older than I am, because I was wearing garments that are trendy among teenagers. I liked the separate elements of this attire, but I wouldn't wear them all together again.

Day 7: The Harry Potter Tee, Plaid Shirt, High-Waisted Shorts & Trendy Tights

Checked Shirt As Before / Tee & Shorts, Author's Own / Abigail 3 Hoop Glitter Tights Sold Out Similar Style, $14, / Boots As Before

Brooklyn hipsters appear dead set on differentiating themselves from the crowd, so I wore some high-waisted, retro style shorts that showed off my unusual tights. I wore a Harry Potter tee as it appears to be "trendy" to be seen as a Harry Potter fan nowadays; in the same way that rocking an interesting moustache, collecting cacti, and supporting independent coffee shops are fashionable pursuits. Lastly, I finished off with a classic plaid shirt because in hipsters eyes, plaid is rad.

I was feeling a little unsure about this outfit at first, but after some compliments from friends, I felt a lot more confident. I was attending a show at the theatre, so I'd initially felt way too underdressed, but after the nice comments (including kind words from a stranger) I felt much better about it.

In fact, I fell in love with the tights — IMO they made an edgy nod to Suicide Squad 's Harley Quinn, whom I have a huge girl crush on. I also love Harry Potter and I don't care who knows.

So What Did I Learn?

Being a Brooklyn hipster is about so much more than fashion; it's a state of mind. It's quite tricky to keep up with — I have way too much going on to be contemplating what top makes me look like I don't care about how I portray my personality to the world, when really I care quite a lot. What can I say, I like aesthetics.

That being said, my week in Brooklyn hipster fashions made me wonder if I've slightly grown out of caring what people think of my appearance, or I feel gross about wearing outfits that don't actually epitomize my personal style, but make me look like all of the other hipsters — or at least, what I think a hipster is. Perhaps it's a bit of both. All I know for sure is, though I'm not entirely sure how a Brooklyn hipster self-identifies or dresses, this was a really fun experiment to try.

Images: Phoebe Waller