I can handle 6-inch Jimmy Choos, hours in a corset dress and a Birkin full of September issue fashion mags. But one uncomfy item you’ll never catch me in? Too-tight jeans. Unfortunately for Kim Kardashian’s lady part, the reality star doesn’t agree and squeezed her nether regions into an appallingly painted-on pair of pants during a jaunt around Manhattan. Ladies, don’t abuse your, ahem, undercarriage by committing this painful fashion don’t!

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Fashion Don’t: Kim Kardashian’s Tight Squeeze

Listen closely my It-Girls-in-training: Smelly little cigarettes are never one of my accessories–why, the dry cleaning bill alone would (almost) be enough to put me in the poorhouse! But unfortunately Demi Lovato didn’t get the memo because I spied the “Skyscraper” starlet toting around a pack of Marlboros yesterday in LA. After working so hard to get healthy, doesn’t it make you sad to see Demi derail? Or is her nasty new habit only making her seem deliciously dangerous?

Photo credit: Flynet / HollywoodLife.com

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Fashion Don’t: Demi’s Disgusting New Habit

Finally, a gift for the nearsighted It Girl who has everything! An optometrist in India has answered the question no one asked and created gold-plated, diamond-encrusted contact lenses, for a mere $16,000. He claims the pricey vision correctors are totally safe and that soon men will start proposing with his contact lenses instead of diamond rings. Sorry Doc, but I’d rather slip something on my finger than poke it into my eye…XOXO

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Fashion Don’t: Diamond Encrusted Contact Lenses

Prepare to be shocked: Someone from Jersey Shore committed a major red carpet sin. Sammi Sweetheart is certainly no stranger to hair extensions of all kind, but she turned up at the VMAs with a rebellious faux lash. Tsk tsk, Sammi; too bad your lashes aren’t as clingy as Ron…

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Fashion Don’t: Sammi Sweetheart Lashes Out

If you’ve ever wondered “Why doesn’t John Mayer dress more like a South American fortuneteller?” then today is your lucky day, my loves. The playboy singer, who infamously inspired Taylor Swift’s ballad “Dear John”, looked all kinds of ugly at Hollywood eatery Katsuhia, thanks to a pair of harem pants and gaucho hat. Does this new style need to be deported? Or is it a look that only Taylor could love?

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Creepster Alert: John Mayer

With all the superb sunglasses on the market, I’m not too sure why Anne Hathaway chose these retro-wannabe shades for her appearance on The Daily Show with Jon Stewart. I can only hope this is a misplaced attempt to get into character for her new role as Catwoman, but I’d almost rather see her cough up a furball than wear these granny glasses again. Would you don this oversized eyewear?

Photo credit: Richie Buxo / Splash New

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Fashion Don’t: Anne’s Cat Eyes

It’s a well-known fact in Hollywood that the more makeup you wear, the less relevant you’re becoming. Keep that in mind as you take a good hard look at American Idol’s Pia Toscano, who donned three days worth of eyeliner at dinner in LA with BF Mark Ballas. Should she give this look back to Taylor Momsen, or is her uber-eye makeup just as intense as her talent?

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Fashion Don’t: Pia’s Panda-monium

When the air turns crisp and my bare little legs are in danger of freezing, tights are my go-to accessory. But in August? Naya Rivera covers up her gorgeous gams in these L’Eggs-looking pantyhose at the premiere of Glee: The 3D Concert Movie in (sweltering) Los Angeles and ruins a possibly perfect red carpet look. Don’t you think Naya should have ditched the nylons and let this stunning Rue du Mail dress take center stage instead?

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Fashion Don’t: Naya Rivera’s Nylon Nightmare

Not everyone can channel Victoria Beckham and sashay through the airport in 5-inch Louboutins and a skintight pencil skirt…but Ashley Tisdale probably shouldn’t be taking travel style tips from Pam Anderson either. Zac Efron’s BFF seems to have left her pants at the security check as she strolled through LAX Tuesday night, arriving home after a weekend in Miami with new pal Julianne Hough. Do you love Ash’s leggy look or is this patriotic sweater an action of sartorial treason?

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Fashion Don’t: Ashley Tisdale’s Stars & Stripper Look

Easy breezy summer dresses have been all over Hollywood this season. And, in a selfless act of public service, Jessica Szohr recently demonstrated how not to wear this warm-weather style. J’s shapeless DKNY maxi looks more like a magic eye picture than a party dress–saved only by the fact that she’s beautiful enough to distract your eyes from her distracting frock. Don’t try this at home, darlings–unless you’re as hot as Jess.

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Instead, take a cue from Kourtney Kardashian at the lia sophia industrielle II collection launch in LA. KK wisely belted her Robert Rodriguez gown to avoid getting lost in her frock’s baggy fit and busy pattern.

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Photo credit: Joe Scarnici

How would you have dressed up JS’s potentially-gorgeous gown?

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Fashion Don’t: Jessica Szohr