A British clothing brand stereotypically made for the 'posh, private school kids'. Similar to Abercrombie & Fitch, except you basically have to be rich to be able to afford more than two pieces of Jack Wills clothing at one go... I myself go to a private school and Jack Wills is quite like the epitome of 'look-here-bitch-I'm-richer-than-you' around here. Luckily, I am not part of that elite group of Jack Willians.
1. Lily: "So, what're you gonna wear to town this Saturday?"

Catherine: "Isn't it obvs? My Jack Wills shirt, pink and blue Jack Wills blazer, Jack Wills jeans, Jack Wills socks, Jack Wills hat, Jack Wills bag, Jack Wills heels..."

Lily: "...Jack Wills don't do heels..."

Catherine: "...... Fuck you, peasant!"

2. Izzy: "I'm thinking of painting my bedroom this week."

Anna: "Oh cool. What colour are you going to paint it?"

Izzy: "I'm gonna do the Jac Wills stripes! They're just so cool! But I have to measure out each stripe, I think they come to about 5cm each?"

Anna: "(obviously scared) Oh... cool?"
by makvcupi April 17, 2011
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Something that an entire generation wear even though it seems to be no more well made than just about anything else on the high street.jack wills is a horrendous exploitation. People buy a frankly rather ugly £60 hoodie as a status symbol, because they like to pretend they're rich and think they can buy their way into something they're not.
I hope the people buying it soon realise they're wasting their money; you could get something nice for that amount. It's not even remotely interesting; or well made to top everything off.
"omg, it's only £60 for this hoodie that says JACK WILLS! what a BARGAIN"
by unprecendented January 18, 2009
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The Quintessential British Preppy Brand

A clothes brand, the british alternative to Abercrombie and Fitch but much more exclusive to those who can afford it. JW has a rock solid, traditional British heritage, inspired by vintage sportswear, beachwear and classic British public school style. It is the epitome of British preppy cool. Customers who are mainly sloanes and preps are unarguably beautiful and sexy. They are the popular guys and girls in class. They are confident and they ooze effortless style. They adore a hedonistic party. And they are ever so, ever so laid back. It is the complete opposite to anything remotely chavvy such as adidias or lonsdale.
Sloane- hey darls, dont you just love my new jack wills trackies

Sloane 2- er yar, theyre far superior to those common adidas ones worn by the peasants.

sloane- how could they wear such cheap rubbish.
by polo_player May 11, 2006
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Over-priced British clothing brand, mainly aimed at apparently rich university and private school students more commonly known as Rahs. However, this brand is really only worn by those without the money or style to buy real designer clothes such as Armani, Dior, Ed Hardy etc.
Rah Girl: "Oh Tarquin darling, have you seen the latest Jack Wills handbook, there are some gorgeous trackies in there for only £70!!"

Rah Boy: "I have Henrietta, isn't Jack Wills so wonderful for rich, stylish folk such as us!"

Genuine wealthy person: "If you did have money or style, you would be wearing proper designer clothes, stupid Rahs!"
by Matt Clay June 26, 2009
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A rich person's clothing brand which is mainly worn by public school pupils with posh names such as Rupert, William, Jonathan, Henrietta, Emilia and so on...
Ah he's/she's very rah wearing Jack Wills!
by hcdh January 2, 2011
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The U.K version of Abercrombie and Fitch. They sell preppy, good quality clothes and loads of comfy, warm hoodies. The price tags are quite high, but you get what you pay for.
person 1: i love your hoodie, where's it from?
person 2: (turns around) jack wills it says on the back ! :)
by Puolly February 16, 2010
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A fairly expensive clothing brand worn by those who can afford it - these people are often called sloanes by people who can't afford it. Everybody goes on about the fact that Jack Wills is cheap, tacky blah blah blah. Well tbh Why the fuck are you going on about it, who gives a shit whether you like or not, they blates do so why waste your time moaning about it.
Despite what you think not all people who buy Jack Wills go Yar and go off to country club. I should know but just to say I do go to a private school, I like some Jack Wills clothing but I don't have any and I couldn't give a shit. You're giving them bigger egos because you actually care!!!!
Oh I love your shirt, is it Jack Wills?

Yeah

by LiLiLiLiLiLi July 11, 2008
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