If someone has a friend send an email this long about how they dress like a piece of shit, they prob need a new wardrobe.

Time to reload the Miltons machine. Send all sob stories to pimpmylook@barstoolsports.com or pimpmydate@barstoolsports.com and help us help you. And you need to send pictures! If you sent an email without a picture resend with one to be considered.

Today’s Contestant

Reader Email


This is my buddy and roommate William.  We are both seniors at NYU, and he is premed/philosophy.  He’s hoping to join the SEALs after graduation in May and do that for a few years before going through the medical school application process.  That’s basically where the good ends.  Really studious guy, but an insane goofball.   He is an absolute slob.  He blames it on coursework taking up all his time, but I’m at the business school at NYU with more difficult classes, and I still manage to be able to put myself together every day, so no pity there…He’s been growing his hair out for about a year now, and it looks awful.  He’s greek, and went from looking like the son of a greek shipping-magnate, to now where he looks homeless.  He knows it doesn’t look good but is carrying it out as a twisted “social experiment” and I am legitimately too ashamed of the way he dresses or looks to invite him out to party when I go out.  Now, the way he dresses is another matter in and of himself.  The kid had no shame:  He does BJJ a few times per week,but proceeds to wear the same clothes from the gym out to dinner or to the library or what have you.  He legitimately never washes–instead of washing his clothes, he runs to the Duane Read and buys a 5-pack of hanes white tee shirts and wears them without washing them until they are crusty and worn out, then goes out and buys another pack.  He has one pair of black jeans with a hole in the crotch area from wearing them so frequently.  He has gotten caught sitting on the floor or whatever with his testicle hanging out a bunch of times.  He is ALWAYS wearing a ski jacket, headband, and sandals regardless of the weather, and wears the same clothes day in and day out, without watching.  Legit wakes up a bit before class and smells whatever clothes are on the floor and makes a judgement call as to what smells the least.  He looks like a homeless guy, which his family is ashamed of just as much as I am.  He comes from a very wealthy family in Florida, and I know they are embarrassed about what he looks like considering they are from such a pretentious community.  Really really nice and smart individual though, but the kind of guy who is just incredibly lazy when is comes to things he finds superficial.  The pics are a great chronological story of our time together throughout college, note the hair length…
1 Stars2 Stars3 Stars4 Stars5 Stars6 Stars7 Stars8 Stars9 Stars10 Stars (327 votes, average: 3.09 out of 10)
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