Haute Hefner | What not to wear

October 4, 10:56 AMChicago Style ExaminerJennifer Rifkin

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                     Don't let this be you!

In the endless litany of style, we rely on the gods of fashion to direct us toward a path of couture enlightenment. Diane, does this wrap dress make my ass look big? Calvin, will I look crazy if I pop my white collar? Christian, do you swear these heels don’t make me look like a hooker?

Yet in all the extravagant designer name-dropping, I would risk my runway reputation to say that you will never hear a woman on her knees begging style status from Hugh Hefner.  On her knees for an alternate reason, perhaps, but this is not the time or the place for that discussion.

Hugh Hefner defines decades of fashion with one standout piece of apparel, the robe.  A shoddily sewn swatch of fabric meant primarily for after bathing, before dressing coverage. Sexy silk or funky flannel aside, this garment is best friends with pajamas and an evening on the couch with ice-cream and a book…not the bar scene on a Saturday night. Leading me to exhibit A – the photograph above of a perfectly good looking gentleman hitting the streets for a night out on the town, adorned in a shabby cream robe reminiscent of Blanche from the Golden Girls, then topped off for good measure with a woven-straw, studded cowboy hat.  Hot factor? Negative thousands.

Is it Halloween? A strangely themed frat party? The victim of a house fire that left them with only these few belongings? Alas, this is just an indulgent showcase of one young man, suffering from either very low self esteem, possibly some abandonment issues, lack of a mirror (obviously burned in the fire) or a general disregard for societal normalcy’s and female attraction. This look almost induces the same violent reaction as when I was hit on by a guy wearing a denim button up embroidered with Looney Toons characters.

Boys and girls alike, this isn’t a good look! There is no plausible reason to outfit yourself in such random pieces, and then parade around seeking attention and accolades.  Want to step outside the box? Try a new pattern, a new color, a pair of deliciously haute high heels or a scarf that elite European men wear, even if it makes you feel a bit femme. Need a jacket? Experiment with corduroy and elbow patches, not belted ragamuffin robes. Thinking about a hat? Chic fedoras in muted colors like navy and grey are the appropriate risk taker…cowboy hats are relegated to actual rodeo participants. Those hotshots ready to hit West Texas with some spurs and serious skills would beat you up for choosing straw and studs over a true horsehair hide.

A psychological session would teach you that clothes are an expression of yourself; dress on the outside to reflect who you are on the inside. Whether that means you are a vegan eating PETA loving activist adorning yourself in organic cotton and hemp, or an OCD corporate lawyer layering power suits over lacy lingerie, it's all about projecting your personality through pieces that make you feel comfortable, confident, and carefree. So I suppose if flip flops a fuzzy robe and cowboy hats are a reflection of multiple personalities, wrangler meets playboy meets California living, then who am I to judge.  Just don’t pair it up with a cartoon character denim shirt …I think I might start crying.