From Warhol and Velvet Underground to Lena Dunham and Girls, New York is one of those places that keep on reeling out the new cool. Set foot in Manhattan and you’ll instantly feel a tad bit cooler.

Unfortunately for you, the New York-hipster would ultimately look down on such a statement, as the t-shirt slogan we found in Brooklyn quite bluntly puts it “Manhattan, you’re ugly and I don’t like you anymore. I <3 Brooklyn.” But worry not, we have the insider info to make sure you get it right.

What to wear

Chicks

Looking effortless is the highest ambition for any New York hipster chick. No one wants to be a try-hard. And whilst your hipster mates across the sea are channeling scruffy-chic, NY is more chic-chic. Just like the screen that displays the latest NYC indie flick, the division between you and them is a tough one to break.

Short, shift LBD’s, ankle boots and a well-kept vintage biker is your safest bet. The Reformation is perhaps the hottest label right now, merging fashion and environmentally sustainable thinking in a luscious compote of cool.

Dudes

Choose between street wear or tailored, but make sure you pay attention to the details. Less is more, even if you go for the street-wear look, and whilst it might be inspired by the 80’s and look an awfully lot like Fresh Prince of Bel Air, you don’t want to end up looking like you’re heading to a fancy dress party (those are out, btw). Get onto the new street wear labels such as LPD New York and 10.Deep for that retro look with a modern twist.

Prefer your well-cut blazers to ironic snapbacks? Buy some dead-stock vintage fabric, get yourself a tailor, Google Taavo Somer, grow a beard and you’re good to go.

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Where to eat

Braised, steamed, raw, fried, deep fried. What are we talking about? Well, kale of course! If it’s not on the menu, run for your money, the place you’ve just stumbled across is way behind. We don’t really know what it is but our guess is some sort of healthy grass. Maybe it’s cabbage. Or lettuce. Truth be told, it’s hardly a taste sensation on its own, but these hip NYC chefs can make everything tasty.

If you really want to outshine your competition (it will be hard), rent a unique space and host your own dinner party. I don’t think we need to mention what should be on the menu. Or do the safe thing and book a table here:

Marlow & Sons

81 Broadway Brooklyn, NY 112249 (718) 384-1441

When we were here we had the garlic–braised, warm kale salad. We have never tried a more satisfying and moreish dish (where the main ingredient is a weird vegetable) before. Brooklyn based Marlow & Sons is so hipster they won’t put any ingredients on the menu. You can choose from “Chorizo” or “Cauliflower” and unless you ask the waiter what it actually is, the anticipation for your meal to arrive is worth going for on its own.

Five Leaves

18 Bedford Ave., Greenpoint, Brooklyn 11222, (718) 383-5345

This hipster hangout on the border of Greenpoint and Williamsburg serve (apart from a few options of kale) fantastic oysters and some pretty stunning truffle-fries. As they don’t take reservations (smart move) expect to wait for up to an hour and a half at busy times. But yes, it’s worth it, as you’ll walk away feeling inferior (at cooking) and superior (for getting a table) at the same time.

Dimes

143 Division Street, NY 10002 (212) 240-9410

If Brooklyn Bridge is broken and you have stay in Manhattan, head to the lower lower east side (take notice of the double lower) and have brunch at newly opened Dimes. Run by Alissa Wagner, previously at Five Leaves, this place offers healthy and simple food in clean Scandi-inspired settings. Be sure to check out the weekly flower arrangements and pick up some sweet looking ceramic pots whilst you’re at it.

Where to drink

You will notice that most restaurants give you water as soon as you have sat down. We know what you’re thinking; ask for San Pellegrino, but your gut is so last season. It’s all about filtered tap water. If the place you’re at has this, you know you should stay. And come back. For more delicious filtered tap water. Were you thinking about something slightly more alcoholic? Pack your ID and get in line at these places:

Leadbelly

14 Orchard St, NY 10002, (646) 596-9142

This trendy hot spot in lower east side was an “only-for-those-in-the-know”-place until Lady Gagatweeted that she got denied entrance. Don’t worry, just because it’s now been in the New York Times doesn’t mean it has lost its hipster aura. Gets crowded on the weekend, with MacBook DJ’s, fuss free cocktails, stubbies and oysters on the menu. All-round good times.

St. Mazie

345 Grand St, Williamsburg, Brooklyn 11211 (917) 443-0848

Sorry to put this out there, but everyone in in this Willyburg hang out is cooler than you are. That won’t stop you from having a great night though. Forget about the rest of the world and get transported into this surreal parallel universe of hip flamenco dancers and street jazz. Sip cocktails on the patio and pretend you’re in a movie.

The Levee

212 Berry St, 
Brooklyn, NY 11211 (718) 218-8787

It’s cheap. It’s open late. It caters micro-breweries. It’s W’burg. It may not be the newest kid on the block, but it’s the one you head to when you just want some cheap, good booze and a long night with like-minded individuals. Rumors say it used to be a cocaine bar called Kokies. Nuff said.

Where to shop

No doubt Manhattan is a mecca for shopping. Pretty much every street offers a clothes shop of some sort. But when you’re bored of your 5th Avenue, Madison Avenue, Browns and Saks you should work your way down the island. First stop Meatpacking district and Soho for your Marc Jacobs, Rag & Bone and other slightly pricier but oh-so-yummy NY labels. Then give your purse a break and venture out to Brooklyn for your vintage and indie designers. Not sure where to start? Try here:

Brooklyn Flea

80 North 5 St. (at Wythe Ave.), Williamsburg

Unique is word that is very close to any real hipster’s heart (by unique we mean the same as all other hipsters) and at the Brooklyn Flea Market you can pick up unique brick-a-brac for every part of life. Buy antiques for your Williamsburg loft, vintage clothes for your IKEA wardrobe and great tasting food from all over the world to claim the epithet “cultured”. No, seriously. This place is amazing. It’s open every weekend and hosted indoors when the weather gets too cold. One of the best flea markets in the state!

Beacons Closet

88 N 11th Street, Brooklyn, NY 11211 (718) 486-0816

Without a doubt the best vintage in Brooklyn, Beacons Closet has had its acclaimed legend-status since it first opened in 1997. It’s easy to lose a couple of hours rummaging through the brilliantly merchandised vintage pieces for both men and women. Short on cash? Don’t worry, bring your unwanted clothes and receive 55% store credit or 35% cash on the re-sale price of all your items. It’s not only environmentally friendly, any clothes that can’t be re-sold will be donated to charity too (unless you decide to keep them).

Dalaga NYC

150 Franklin St., Brooklyn, NY 11222 (718) 389-4049

Dalaga was the first boutique to open on the now thriving Franklin Street in Brooklyn. Run by the sister duo Michelle and Mary, Dalaga nails everything from on-trend dresses and cosy knitwear to quirky accessories. It won’t hurt your wallet either, as most items lie comfortably under the $100 mark. Aside from bringing in independent designers, Dalaga also offer their own lines of jewelry and fragrances.

Looking for more hipster fun? Take a look at our guide to New Yorker vs Londoner stereotypes.