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Chip off the ole Book
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I like Chip Kidd. Like me, he wears woolen flat caps. Anyhoo he and Lisa Birnbach have a new book coming out: True Prep, which is a sequel to The Official Preppy handbook. A review of the book is in progress and I was fingered to do some logo send-ups (or cast downs) for it.
If writing comedy is tough, designing comedy is tougher. It has to work on it's own (written, as seen here), as a logo design, and within the context of the overall thematic.
I've done this one before ("SARS" with Fuchs for Nicholas Belchman's Nozone book) We actually redrew the lion as a chicken in that one.
Timmy Hilniger was a Spike Lee joint (I forget which movie). Not sure if this one works or not as Tommy is something of an impure prepster.
not terribly funny, but....
This one is better, only because I'm into spencerian marks. Here is a bit of Wikihistory:
 

Spencerian Script is a script style that flourished in the United States from 1850 to 1925.[1]

Platt Rogers Spencer, whose name the style bears, was impressed with the idea that America needed a penmanship style that could be written quickly, legibly, and elegantly to aid in matters of business correspondence as well as personal letter-writing.

Spencerian Script was developed in 1840, and began soon after to be taught in the school Spencer established specifically for that purpose. He quickly turned out graduates who left his school to start replicas of it abroad, and Spencerian Script thus began to reach the common schools. Spencer never saw the great success that his penmanship style enjoyed, having died in 1864, but his sons took upon themselves the mission of bringing their late father's dream to fruition.[2]

This they did by publishing and distributing Spencer's unpublished book, Spencerian Key to Practical Penmanship, in 1866. Spencerian Script became the standard across the United States and remained so until the 1920s when the spreading popularity of the typewriter rendered its use as a prime method of business communication obsolete.

It was gradually replaced in primary schools with the simpler Palmer Method developed by Austin Norman Palmer.

The text in Ford Motor Company's logo is written in this style, as was the original Coca-Cola logo.[3]

Ladies Love Boring logo parodies.
its French, you drink it.
Purists may disagree but I think K Swiss falls into the category. I never had a pair because tennis is gay.
This is one of those really boderline douchebag preppy brands, Burberry. Why was it even in the Mall? This is grampah from England territory.
I'm sorry but fuck you— Polo Marco Polo is funny. OK, maybe you're right. Fine, you're right. Urgh. But you have to admit I nailed Tranny Halfsister.
In case you're wondering, heres what the original looks like. I had never heard of it. Apparently its a big deal to purist prepsters.
and heres the new book. To tell you the truth I like the older cover better. The curvilinear type tosses this back into the 90's for me. Something tells me Chip made Chris Ware draw these damn dogs. 
heres a pic of the famously freaky deaky Chip Kidd. I always respected his choice of headwear (dare we mention anything of his book-design prowess? Nay).
I'm not much into fashion anymore but I do like to rock the woolen cap on occasion. When I do have to dress "non-soccer uniform" I usually shimmy into something old school— say like a Cuban guyabera, linen pants, OluKai surfer sandals, Ray Ban Aviators and Dorfman hat. The thick wollen Polo jacket never fails either. Heres a pic of me and my girls.
btw - this assignment was killed so don't bother looking for it anywhere.
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