On this weeks episode of Entourage we saw Vinnie's weed carrier/driver Turtle start his first day of school, but not before his dime piece of a girlfriend Jamie Lynn Sigler made him ditch his fitteds and graphic tees for bland button downs and khaki's. Not a good look. If the show's producers really wanted to get him ready for class, they could have a) read Complex magazine or b) checked out some of television's most iconic school-aged characters.

Seriously. We looked back through a couple of our most favorite shows, new and old, and saw that most of the characters were mad fly. Stylish enough for you to learn a thing or three from now that it's back to school shopping season. We can't guarantee you'll be as cool as these guys, but, hey, at least you'll look cooler than you did last year.

chuck

1. J.PRESS CRUSHED BOGIE
Click here to Buy It Now at J. Press, $89

2. HERMÉS EX LIBRIS POCKET SQUARE
Click here to Buy It Now at Hermés, $125

3. ASOS TAILORED SLIM FIT SHIRT
Click here to Buy It Now at Asos, $37

4. J.PRESS GUNCLUB PLAID WOOL SPORTSCOAT
Click here to Buy It Now at J. Press, $495

5. J. PRESS 100% ITALIAN FABRIC CORDUROY
Click here to Buy It Now at J. Press, $150

6. OPENING CEREMONY M8 CLASSIC SADDLE SHOE
Click here to Buy It Now at Opening Ceremony, $345

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dylan

1. NUDIE GUSTAV RED LUREX CHECK SHIRT
Click here to Buy It Now at SSense, $100

2. G-STAR 3301 PLUS SUDDEN PARK BREEZE
Click here to Buy It Now at SSense, $279

3. TOPMAN WHITE ROLL CREW NECK T-SHIRT
Click here to Buy It Now at Topman, $12

4. FRYE BRANDO ENGINEER BOOTS
Click here to Buy It Now at Frye, $248

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wayne

1. LENNON OZZY GLASSES
Click here to Buy It Now at Goggles & Glasses, $13

2. OPENING CEREMONY SOE SHIRT 023
Click here to Buy It Now at Opening Ceremony, $131

3. FOLK PEOPLE CARDIGAN
Click here to Buy It Now at Oki-Ni, $322

4. PF-FLYERS CENTER LOW
Click here to Buy It Now at Zappos, $50

5. HOWE MEN'S THE FINEST PANTS
Click Here to Buy It Now at 80's Purple, $95

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will

3. MAUI & SONS SHARK LOGO TEE
Click here to Buy It Now at Opening Ceremony, $35

4. NIKE AIR FLIGHT LIGHT
Click here to Buy It Now at Eastbay, $60

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zack

1. SUPER FLATOP SUNGLASSES
Click here to Buy It Now at Oak, $142

2. KREW JG ACID WASH SHORTS
Click here to Buy It Now at Skate Park of Tampa, $22

3. AMERICAN APPAREL MELANGE JERSEY TANK
Click here to Buy It Now at American Apparel, $17

4. HAPPY SOCKS ODD COUPLE SOCKS
Click here to Buy It Now at Opening Ceremony, $10

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