How To Live Like Chuck Bass: Luxury Hotels, His Iconic Fashion Sense, And How To Spend Your Money

Eleven years after Gossip Girl ended, the hit show still remains as a cultural zeitgeist and pop phenomenon. With the precision of an archaeologist’s eye, it shined a light on what the privileged and elite teenagers do while living in the opulence of the Upper East Side in Manhattan.

To this day, to live like Chuck Bass, played by Ed Westwick, is still every man's dream.  If you want that fantasy to come true, if you want to live like Chuck, there are certain things you must do or possess besides being rich. For example, you need to live on the Upper East Side, preferably under 95th Street. If you are poor and live near the Port Authority and your mother shops at Strawberry, that's strike one. If you go to Pequannock Township High School because you can’t afford to go to Collegiate, you might as well forget about getting into the right liberal arts college (Hint: a LAC is preppier than a university). You also need to shop at Paul Stuart. You need to be philanthropic and donate to charities like The Coalition and Association of the Society Intended For Improvements For A Better Teacher's Lounge at Stuyvesant High, because the last event netted only a freaking $17.86. All that could be bought was 3 new mugs that said, “To Teach Now Allows Us To Touch The Future But Since We Are Only Living In The Present, We Can’t Possibly Touch Something That Hasn’t Yet Come.” If you don’t give to deserving charities like this, that’s strike three and you’re out.

Even so, we have come up with 15 tips on how to live like Chuck Bass.

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15 Get Yourself A Signature Scarf

Planet Claire

First, we need to give credit to Eric Daman, the inspired costume designer for GG who dressed Ed Westwick to the nines. He was the one who found the now iconic scarf that Westwick’s character wore in many episodes.

"Don't mock the scarf, Nathaniel. It's my signature."

The signature item is a patchwork polka-dot silk scarf that was sold at J. Press. If you don’t know the difference between J.Press and J. Crew, and why, then you really, really need to do your research if you're going to be Chuck Bass. Before GG made the scarf famous, a J. Press spokesman said, “They have been around for a few seasons. . . No one really paid much attention to them and they weren’t really selling.” The true power of GG is that it can singlehandedly make a wardrobe or accessory a coveted item, so it’s no surprise that the scarf sold out.

14 You Need To Go To Prep School

Vogue UK

Chuck Bass went to the elite but fictitious St. Jude’s School for boys, which shared a campus with the also fictitious school Constance Billard for girls. If you absolutely must live like Chuck Bass, it is essential that you also go to a prep school on the Upper East Side. All-girls schools like Chapin, Spence and The Nightingale-Bamford School are the only acceptable places that preppy rich girls living in NYC can go to.

If you’re a guy, there's only one school on the UES that you can attend: Dalton. The only thing wrong with it is that it’s co-ed, as same-sex schools are preppier. However, it is the most elite and most prestigious high school in all of New York, and if you don’t know why, that’s because you’re stuck at the Regis or, God forbid, Hunter High.

13 Fly Around The World, Just To Say I Love You

Anyone who is even a little bit of a romantic likes the idea of their partner going above and beyond to please them. Sometimes with words, sometimes with actions, and sometimes with gifts. Well, if you're Chuck Bass, there's only one way to impress your lady before you say "I love you". Chuck is the kind of guy to fly to France and Germany just to pick up stockings and chocolate for the woman he loves. Obviously, he also has his own private jet. If you're going to blow some money, you might as well make sure you're travelling in style.

"The next time you forget you're Blair Waldorf, remember I'm Chuck Bass and I love you."

Sure, he could have gone on a shopping trip in Manhattan, but then he couldn't say that he bought them in Europe. Sometimes, it's not about what you bought, but where you bought it.

12 If You Can't Go To Prep School, Give Up And Attend Cornell

It'll eventually happen if it hasn't happened already. You're at a charity party for The United Anonymous Appeal for The Coalition Of Selfie Sticks As The Ideal Product For Losers Who Have Only Invisible Friends and some stranger will ask you where you prepped. In fact, you'll get this question a lot throughout your life if you run in the right circles. So what do you say?

"For people like us, a college degree is just an accessory. Like a Malawi baby or a poodle."

If you can’t go to Dalton or PEA or Hotchkiss because your grades suck, or if your elevator doesn’t open up to your parents' pre-war penthouse pad, you might as forget all about being like Chuck. Instead you'll get sucked into oblivion at a public school and apply to Cornell because you think it must be good because it’s Ivy League (hint: it is, but it’s not). See, the right high school ultimately dictates where you'll go to college. If you manage to attend college because you got FA and if your school has a major in communications, you’re at the wrong university. While we're at it, “business” is not something you study as an undergrad. You go to grad school to do that, but only if you get into HBS or Wharton.

11 You Have To Know How To Accessorize

Pop Sugar

If Chuck Bass is not wearing a jacket, he’ll still be dressed in a formal dress shirt with a tie, as well as a suit vest. But here’s the Bass twist: he’ll wear bright red suspenders that, of course, will both clash with his overall outfit and yet somehow render it complete. For neckwear, he’ll wear either a bowtie or a tie, and both of them will be colorful. The signature look is a paisley tie, but of course patterns and bright colors are also important.

If Chuck isn’t sporting traditional neckwear, he’ll wear an ascot, which you must know is a type of cravat. You must also remember that ascots are more informal, tied under the collar, and that cravats can also refer to all ties. As for pocket squares, always have it on you if you're wearing a blazer. If you’re not hankering for a handkerchief, place a boutonniere in your breast pocket. One last thing: if you’re wearing an informal blazer, pop the collar up as sharp as a shark’s teeth, the way Chuck does.

10 Break Every Fashion Rule

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The one takeaway you should never forget is that Chuck’s wardrobe rests on a sartorial contradiction: clashing patterns are a must, and they somehow appear perfectly coordinated when Chuck wears them. The look is always luxurious fabrics, quirky details with something that pushes it over the edge. You should break every fashion rule that you can even if it means you're looking like a room with exploding pink wallpaper, navy-and-white cornices over windows, yellow-striped upholstered chairs and Chinese ginger jar vases. Never forget the Three P’s: purple, plaid and preppy.

Do not shy away from bold colors and remember to add pattern at the same time because that's not tacky but a matter of a highly refined and stylized taste. For example, during a beach scene, Chuck wears plaid shorts, a striped shirt and a fedora. This makes him look as if he’s a blind or ailing man who can't dress himself. But it also makes him preppy to the hilt. How? He’s Chuck Bass.

9 Ways To Dress Like A Clown From “It”


In one episode, Chuck tops off his yellow shirt, the school uniform, with a bright red blazer and somehow pulls off the look. Then there was the purple button-down sweater with go-to-hell yellow pants that made him look like Barney the Dinosaur (that one was just for fun).

"Actually I only wear purple because my father loathed it."

Then there was the bright prison-like orange trench coat that made him look like a traffic cone, the tan trench coat paired with black gloves that made him look like a sexy serial killer, the signature jacquard purple silk robe that he wears while drinking scotch whiskey and the many velvet smoking jackets he wears while at home at the Empire.

To some, he may look like a clown straight out of “It,” but those who have taste--those not attending Cornell--know that such bold sartorial combinations are a mark of confidence, which Chuck oozes. Remember these looks and wear them to command sophistication and respect!

8 Drop A Load At Paul Stuart

The Odyssey

Of all the places to hit, Paul Stuart, an English gentleman’s high-end menswear shop, is the place to go for sophisticated haberdashery that doesn’t take itself seriously. Like a hunt scene motif mid-calf hosiery sock that would’ve gone swimmingly well, old chap, with the zip-up navy cardigan with two whales on each side that Chuck actually wore in one episode.

Yep, whales.

Stuart is pricey, so if you don’t have a Black Card, you shouldn’t be there. You should be shopping at Express at the Staten Island Mall rummaging for a suit you can afford. Oh, about that suit? Here’s a question for you: do you think you can get away wearing that to Keith McNally’s Augustine? A suit that is made of 81% polyester, 17% rayon, and 2% spandex is not a suit. And why would you need spandex? So, you can be more flexible? You’re not going to Planet Fitness.

7 Where To Shop If You're Not Sophisticated Enough For Paul Stuart

Brooks Brothers is always a go-to place for the argyle sweaters and vests that Chuck wears. Costume National is a place for the dressed-up but fun look, and Purple Label Ralph Lauren is the place to get a customized suit. J. Press however, combines exquisite tailoring with distinguished colorful designs, and thus makes it the preppiest place to get the Chuck Bass look.

They sell every piece of clothing and accessory you need. There’s the candy-striped banker’s dress shirts, the most colorful repp ties and, of, course, Yale key fobs. The store thinks of everything in terms of Ivy League, and its first store was in New Haven. So, if you went to Boston University and not Princeton, we’ll make this easy for you: don’t bother shopping here. Alas, J.Press does sell Cornell needlepoint belts. If you don’t know why Cornell is not elite, you can stop reading this list now.

6 Travel In Style

Okay, okay, so not everyone can afford a private jet. In fairness, not everyone can afford a limo either, but if you're reading this, it's because you want to be Chuck Bass. So you better find a way to get a limo. If you're going to be rich, then you should have people ready at your beck and call. Sure, you can have just a regular, sleek, black car like most Upper East Siders, but don't you want to be set apart? Don't you want the world to know just how much you're actually worth? Chuck does.

"Say hello to the characters on public transportation for me."

So get a limo. It provides class, and shows everyone where you come from, and how much money you're willing to spend. Besides, if you're going to make it on the Upper East Side, you can't expect to be taking the subway.

5 Buy A Hotel

Curbed NY

If you want to live like Chuck Bass, buy a hotel, but not any hotel. Chuck bought the Empire Hotel, which is an actual hotel on 63rd Street on the Upper West Side. Before GG filmed there, it wasn't exactly a hot commodity. If you wanted to be near Lincoln Center and you have taste, you know to stay at the Mandarin Oriental at Columbus Circle. So get your own hotel, which should be boutique and more exclusive, expensive and debonair than the Empire.

"Why settle for some bar in a hotel, when you can just buy the hotel?"

The Bowery, The Surrey, The Mark, The Greenwich Hotel, The NoMad, should we go on? The list gets longer, and the Empire is not in the esteemed company of these stylish boutique dwellings. Sometimes GG gets it wrong. Like Chuck using a stretch limo to get around when a Lincoln Town Car would suffice. And besides, the Empire is on the Upper West Side. We know, gross. This is the place that is home to a popular market, Zabar’s, whose claim to fame is that it has the best smoked fish in all of the city. Before that, it was known for its bagels. Bagels are not sexy, but at least The Empire is.

4 Attend The Biggest Events Of The Year

Vogue UK

Look, sometimes high end events are plain boring. We know. We also don't care, and neither does Chuck. It's not about what the event is. What makes it important is who shows up. Any event is worth your time if Chuck Bass shows up, and he shows up to all of them.

"We don't need tickets...I'm Chuck Bass."

Events are a time for business opportunities, as well as to show off just how much money you have. Every A-Lister uses it as their moment to try and outshine someone else. Not that anyone could outshine Chuck. So whether you're attending a charity event or a horse race, make sure you have all eyes on you. Pick the perfect suit, wear the perfect gold ring on your pinky, grab your date, and go. Sit back, relax, and let the world come to you. Which it will, because such is the life of an Upper East Sider.

3 Where To Go To College

The Odyssey Online

The GG cast ended up at NYU and Columbia. Chuck opted out of college.

"The only queens at NYU are the ones with tickets to see Liza at Carnegie Hall." 

In case you do want to go to college you should know that NYC and Columbia are both unacceptable. Both of these schools aren’t actually acceptable for an UES preppy teen who comes from money. If you want to live like Chuck Bass or his friends, you know that Columbia is the least preppiest school in the Ivy League; it’s in a moribund section of New York called Morningside Heights. NYU is only acceptable because it’s close to Balthazar.

If you want to prep at an Ivy League, you only have three choices: Yale, Princeton and Harvard. Even preppier is going to a LAC such as Middlebury and Bowdoin which are both are near skiing, the ultimate preppy sport. Amherst and Williams are other good options as both are reminiscent of boarding schools like Milton and PEA. Vassar and Sarah Lawrence are out of the league due to the student body. What’s preppy about androgynous-looking boys and women who don’t shave their legs? If you wear Tevas, then by all means apply ED and die there.

2 You Must Be Dripping In Wealth

Racked New York

Your parents must be very wealthy if you want to access Chuck’s world. Chuck’s father, Bartholomew “Bart” Bass, is a self-made billionaire. If you’re not an heiress or a scion, then at least one of your parents must work on Wall Street. If your father is a sales manager for an irrigation manufacturer, and your mother actually goes Christmas shopping on Thanksgiving for something called “door busters” at the JCPenney’s at the Manhattan Mall, drop out of high school and work for the MTA, above ground preferably.

If your mother is a high school teacher at a “PS 178,200”, and your father makes clocks, or if you have radiators in your rooms and own a station wagon so that you can spend summers in Cape May (we know, gross), you will never be Chuck Bass. Find a way to roll in money in a legal way.

1 Learn How To Speak The Right Way


Ed Westwick is British, but he plays Chuck with an American accent. His locution denotes the speech of the very wealthy, what is referred to as the “Locust Valley lockjaw (LVL)” in reference to the rich who live in Locust Valley in Long Island, according to the New York Times. So when he speaks, he sounds like money. So, of course you need to start talking like Chuck Bass to be Chuck Bass. To do this, keep your mouth closed as much as you can. '

'The enunciation is done principally by movement of the lips, producing a nasal tone,” as the NYT points out.

A raised eyebrow as an added addition is splendid, and the LVL is done best in a whisper. When Chuck talks he closes in on you, and with his eyes nearly closed, it looks as if it’s very painful for him to have a conversation. That’s the look you want. N.B. the original Preppy Handbook also references The Locust Valley lockjaw, so we know Chuck Bass’s speech is authentically preppy.

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