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1.
A West Los Angeles private school at which students are often smart & rich. Unfortunately for other local schools like Archer, Harvard Westlake, Brentwood, Crossroads, and, Oakwood, Students at Windward tend to be better than everyone at nearly everything. A typical "Windward boy" will have 6pack abs, be somewhat metrosexual, and, be incredibly friendly. A "Windward girl" is usually nice, but, can most likely be found with a blackberry in one hand and a Starbucks in the other.
Girl 1: Hey do you go to Windward?

Girl 2: No, why?

Girl 1: Nothing, i thought i recognized you from Starbucks

Windward Boy 1: Hey Bro, after school, wanna go on a run around the park so we can take off our shirts and "accidentally" show our abs to the group of girls by the locker room?

Windward Boy 2: Defiantly, let me just go put my cardigan in my locker and do a few more good deeds.
by YouHadMeAtYourProperUseOfVerbs December 30, 2011
45 8
 
2.
An elite Los Angeles School wherein you will find extremely intelligent individuals who reign supreme in pretty much everything they do. However, they tend to be quite snobby due to their extreme wealth.
Hey you know him?
Yeah he went to windward.
Oh, now wonder he's going to Harvard with his Ferrari.
by 6uf42 September 08, 2010
22 17
 
3.
Something that is full of rich assholes who get their 16 year old kids brand new infiniti's or ferraris or BMWs. Most of the kids are just plain ugly as well. Many are wastes of space.
"you know that guy who just bought a hummer and a yacht?"
"yeah, what about him?"
"He went to Windward"
"Oh. How interesting"
by Homer Sampson February 13, 2008
41 67