<!DOCTYPE html><html lang="en"><head><meta charset="utf-8"><meta name="viewport" content="width=device-width,initial-scale=1,maximum-scale=1,user-scalable=no,shrink-to-fit=no"><title>Miltons Pimp My Look</title><link rel="stylesheet" type="text/css" href="https://htlbid.com/v3/barstoolsports.com/htlbid.css"><script async src="https://htlbid.com/v3/barstoolsports.com/htlbid.js"></script><script async src="https://www.caffeine.tv/embed.js"></script><script>window.htlbid=window.htlbid||{},htlbid.cmd=htlbid.cmd||[],htlbid.cmd.push(function(){htlbid.setTargeting("pagetype","blog"),htlbid.setTargeting("authorId","40"),htlbid.setTargeting("Verity_keywords",["look | barstool sports","intelligent kid","milton pimp","go","shirt","red flannel shirt","danny","history","hello","politic","true squid","dr. creepy","roommate connor","weekend","mystery"]),htlbid.setTargeting("Verity_positive","0.22"),htlbid.setTargeting("Verity_neutral","0.78"),htlbid.setTargeting("is_testing","no"),htlbid.pubads().setPublisherProvidedId("PPID-GOES-HERE"),htlbid.layout()})</script><script src="https://d9rde3y35j061.cloudfront.net/script.js"></script><script src="https://htlbid.com/v3/barstoolsports.com/htlbid.js" async></script><script src="https://iframely.barstoolsports.com/embed.js" async></script><style>.union__content{font-family:-apple-system,HelveticaNeue,Roboto,sans-serif;font-weight:400;font-size:18px;color:#5a5b5d;word-wrap:break-word;box-sizing:border-box;padding:0 5px 32px 5px}.union__content p{padding:0;margin:16px 0 0 0}.union__content img{display:block;width:100%!important;height:auto;margin:16px 0 0 0}.union__content video{display:block!important;width:100%!important;height:auto;margin:16px 0 0 0}.union__content .articleAd{text-align:center;margin:16px 0 0 0;background-color:#f5f5f5}.union__content .htlad__container{display:inline-block}.union__content p a{color:#377dc4}.union__content .oembed__wrapper{margin:16px 0 0 0}.union__content blockquote:not(.twitter-video){display:block;margin:16px 0 0 0;padding:4px 12px;border-left:4px solid #77889a;font-style:italic;background:#f0f4f8;text-align:left;border-radius:0 6px 6px 0}.union__content blockquote:not(.twitter-video) p{font-style:italic}.union__content blockquote,q{quotes:none}.union__content iframe{max-width:100%}.union__content .bs-image-hidden{display:none}.union__content div.hq-image{width:fit-content;margin:0 auto}.union__content span.image-attribution,.union__content span.image-attribution a{color:#757575;font-size:12px;font-style:italic;letter-spacing:.1px;line-height:14px;text-decoration:none;padding:0;margin:0}.union__content .bs-videoPlayer .bs-videoPlayer__container,.union__content video-js,.wp-video{width:100%!important;height:0!important;position:relative;padding-bottom:56.25%;overflow:hidden;margin:16px 0 0 0}.wp-video video{width:100%!important;height:100%!important}.hq-image video{width:100%!important;height:100%!important}.union__content .bs-videoPlayer__container>iframe{position:absolute;top:0;left:0;width:100%;height:100%;border:none}@media (prefers-color-scheme:dark){.union__content,body,html{background:#1c1c1c;color:#f1f1f1}.union__content blockquote:not(.twitter-video){border-left:4px solid #367dc4;background:#272c35}}</style><script>window.addEventListener("applicationDidBecomeActive",()=>{document.querySelectorAll(".hq-image video[autoplay]").forEach(e=>e.play())})</script><script>window.htlAdUnitPath="57249056/in-app-iOS/Article-Page_In-Article-Unit",window.htlKeyvalues={authorId:"40",category:"No category",tags:[],brandName:null,brandId:0,pagetype:"standard_post"}</script></head><body class="union__content"><a href="http://boston.barstoolsports.com/random-thoughts/miltons-pimp-my-look-38/attachment/m1-12/" rel="attachment wp-att-120100"><img title="m1" alt src="http://boston.barstoolsports.com/files/2012/11/m11.png" width="292" height="266" sizes="(max-width: 1080px) 100vw, 776px" loading="eager"></a>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<a href="http://boston.barstoolsports.com/files/2013/11/dooley-1.jpg"><img class="alignnone size-large wp-image-171975" alt="dooley 1" src="http://boston.barstoolsports.com/files/2013/11/dooley-1-480x616.jpg" width="480" height="616" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"></a> <a href="http://boston.barstoolsports.com/files/2013/11/dooley-2.jpg"><img class="alignnone size-large wp-image-171976" alt="dooley 2" src="http://boston.barstoolsports.com/files/2013/11/dooley-2-478x640.jpg" width="478" height="640" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"></a> <a href="http://boston.barstoolsports.com/files/2013/11/dooley-3.jpg"><img class="alignnone size-large wp-image-171977" alt="dooley 3" src="http://boston.barstoolsports.com/files/2013/11/dooley-3-480x581.jpg" width="480" height="581" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"></a> <a href="http://boston.barstoolsports.com/files/2013/11/dooley-4.jpg"><img class="alignnone size-large wp-image-171978" alt="dooley 4" src="http://boston.barstoolsports.com/files/2013/11/dooley-4-480x360.jpg" width="480" height="360" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"></a> <a href="http://boston.barstoolsports.com/files/2013/11/dooley.jpg"><img class="alignnone size-large wp-image-171979" alt="dooley" src="http://boston.barstoolsports.com/files/2013/11/dooley-480x640.jpg" width="480" height="640" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"></a>   Reader EmailHello,This is my roommate Connor, aka Dr. Creepy. He is a very intelligent kid when it comes to history and politics and what not but when it comes to putting on clothes it looks like he gets dressed in the dark most of the time. Where he gets some of these shirts he owns is a mystery to all of us. He can’t go a weekend without sporting his go to red flannel shirt with the USA shirt underneath it. And as for the snowman T-Shirt he’s wearing in one of the pictures he legitimately thinks it stylish. Anytime the kid gets dressed and we question what he’s wearing he always says his go to catchphrase “I think it’s just nifty!”. The kids a true squid so please help out this poor bastard and teach this kid how to dress, because at the age of 22 he still has yet to figured it out.Thanks,Danny<div class="rating"><img id="rating_171974_1" src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/stars_crystal/rating_on.gif" alt="1 Star" title="1 Star" onmouseover='current_rating(171974,1,"1 Star")' onmouseout="ratings_off(7.4,8,0)" onclick="rate_post()" onkeypress="rate_post()" style="cursor:pointer;border:0" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"><img id="rating_171974_2" src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/stars_crystal/rating_on.gif" alt="2 Stars" title="2 Stars" onmouseover='current_rating(171974,2,"2 Stars")' onmouseout="ratings_off(7.4,8,0)" onclick="rate_post()" onkeypress="rate_post()" style="cursor:pointer;border:0" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"><img id="rating_171974_3" src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/stars_crystal/rating_on.gif" alt="3 Stars" title="3 Stars" onmouseover='current_rating(171974,3,"3 Stars")' onmouseout="ratings_off(7.4,8,0)" onclick="rate_post()" onkeypress="rate_post()" style="cursor:pointer;border:0" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"><img id="rating_171974_4" src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/stars_crystal/rating_on.gif" alt="4 Stars" title="4 Stars" onmouseover='current_rating(171974,4,"4 Stars")' onmouseout="ratings_off(7.4,8,0)" onclick="rate_post()" onkeypress="rate_post()" style="cursor:pointer;border:0" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"><img id="rating_171974_5" src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/stars_crystal/rating_on.gif" alt="5 Stars" title="5 Stars" onmouseover='current_rating(171974,5,"5 Stars")' onmouseout="ratings_off(7.4,8,0)" onclick="rate_post()" onkeypress="rate_post()" style="cursor:pointer;border:0" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"><img id="rating_171974_6" src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/stars_crystal/rating_on.gif" alt="6 Stars" title="6 Stars" onmouseover='current_rating(171974,6,"6 Stars")' onmouseout="ratings_off(7.4,8,0)" onclick="rate_post()" onkeypress="rate_post()" style="cursor:pointer;border:0" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"><img id="rating_171974_7" src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/stars_crystal/rating_on.gif" alt="7 Stars" title="7 Stars" onmouseover='current_rating(171974,7,"7 Stars")' onmouseout="ratings_off(7.4,8,0)" onclick="rate_post()" onkeypress="rate_post()" style="cursor:pointer;border:0" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"><img id="rating_171974_8" src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/stars_crystal/rating_half.gif" alt="8 Stars" title="8 Stars" onmouseover='current_rating(171974,8,"8 Stars")' onmouseout="ratings_off(7.4,8,0)" onclick="rate_post()" onkeypress="rate_post()" style="cursor:pointer;border:0" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"><img id="rating_171974_9" src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/stars_crystal/rating_off.gif" alt="9 Stars" title="9 Stars" onmouseover='current_rating(171974,9,"9 Stars")' onmouseout="ratings_off(7.4,8,0)" onclick="rate_post()" onkeypress="rate_post()" style="cursor:pointer;border:0" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"><img id="rating_171974_10" src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/stars_crystal/rating_off.gif" alt="10 Stars" title="10 Stars" onmouseover='current_rating(171974,10,"10 Stars")' onmouseout="ratings_off(7.4,8,0)" onclick="rate_post()" onkeypress="rate_post()" style="cursor:pointer;border:0" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"> (171 votes, average: 7.43 out of 10) </div><img src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/loading.gif" width="16" height="16" alt="Loading..." title="Loading..." class="post-ratings-image" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy">Loading... </body></html>

<a href="http://boston.barstoolsports.com/random-thoughts/miltons-pimp-my-look-38/attachment/m1-12/" rel="attachment wp-att-120100"><img title="m1" alt src="http://boston.barstoolsports.com/files/2012/11/m11.png" width="292" height="266" sizes="(max-width: 1080px) 100vw, 776px" loading="eager"></a>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<a href="http://boston.barstoolsports.com/files/2013/11/dooley-1.jpg"><img class="alignnone size-large wp-image-171975" alt="dooley 1" src="http://boston.barstoolsports.com/files/2013/11/dooley-1-480x616.jpg" width="480" height="616" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"></a> <a href="http://boston.barstoolsports.com/files/2013/11/dooley-2.jpg"><img class="alignnone size-large wp-image-171976" alt="dooley 2" src="http://boston.barstoolsports.com/files/2013/11/dooley-2-478x640.jpg" width="478" height="640" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"></a> <a href="http://boston.barstoolsports.com/files/2013/11/dooley-3.jpg"><img class="alignnone size-large wp-image-171977" alt="dooley 3" src="http://boston.barstoolsports.com/files/2013/11/dooley-3-480x581.jpg" width="480" height="581" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"></a> <a href="http://boston.barstoolsports.com/files/2013/11/dooley-4.jpg"><img class="alignnone size-large wp-image-171978" alt="dooley 4" src="http://boston.barstoolsports.com/files/2013/11/dooley-4-480x360.jpg" width="480" height="360" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"></a> <a href="http://boston.barstoolsports.com/files/2013/11/dooley.jpg"><img class="alignnone size-large wp-image-171979" alt="dooley" src="http://boston.barstoolsports.com/files/2013/11/dooley-480x640.jpg" width="480" height="640" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"></a>   Reader EmailHello,This is my roommate Connor, aka Dr. Creepy. He is a very intelligent kid when it comes to history and politics and what not but when it comes to putting on clothes it looks like he gets dressed in the dark most of the time. Where he gets some of these shirts he owns is a mystery to all of us. He can’t go a weekend without sporting his go to red flannel shirt with the USA shirt underneath it. And as for the snowman T-Shirt he’s wearing in one of the pictures he legitimately thinks it stylish. Anytime the kid gets dressed and we question what he’s wearing he always says his go to catchphrase “I think it’s just nifty!”. The kids a true squid so please help out this poor bastard and teach this kid how to dress, because at the age of 22 he still has yet to figured it out.Thanks,Danny<div class="rating"><img id="rating_171974_1" src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/stars_crystal/rating_on.gif" alt="1 Star" title="1 Star" onmouseover='current_rating(171974,1,"1 Star")' onmouseout="ratings_off(7.4,8,0)" onclick="rate_post()" onkeypress="rate_post()" style="cursor:pointer;border:0" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"><img id="rating_171974_2" src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/stars_crystal/rating_on.gif" alt="2 Stars" title="2 Stars" onmouseover='current_rating(171974,2,"2 Stars")' onmouseout="ratings_off(7.4,8,0)" onclick="rate_post()" onkeypress="rate_post()" style="cursor:pointer;border:0" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"><img id="rating_171974_3" src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/stars_crystal/rating_on.gif" alt="3 Stars" title="3 Stars" onmouseover='current_rating(171974,3,"3 Stars")' onmouseout="ratings_off(7.4,8,0)" onclick="rate_post()" onkeypress="rate_post()" style="cursor:pointer;border:0" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"><img id="rating_171974_4" src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/stars_crystal/rating_on.gif" alt="4 Stars" title="4 Stars" onmouseover='current_rating(171974,4,"4 Stars")' onmouseout="ratings_off(7.4,8,0)" onclick="rate_post()" onkeypress="rate_post()" style="cursor:pointer;border:0" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"><img id="rating_171974_5" src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/stars_crystal/rating_on.gif" alt="5 Stars" title="5 Stars" onmouseover='current_rating(171974,5,"5 Stars")' onmouseout="ratings_off(7.4,8,0)" onclick="rate_post()" onkeypress="rate_post()" style="cursor:pointer;border:0" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"><img id="rating_171974_6" src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/stars_crystal/rating_on.gif" alt="6 Stars" title="6 Stars" onmouseover='current_rating(171974,6,"6 Stars")' onmouseout="ratings_off(7.4,8,0)" onclick="rate_post()" onkeypress="rate_post()" style="cursor:pointer;border:0" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"><img id="rating_171974_7" src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/stars_crystal/rating_on.gif" alt="7 Stars" title="7 Stars" onmouseover='current_rating(171974,7,"7 Stars")' onmouseout="ratings_off(7.4,8,0)" onclick="rate_post()" onkeypress="rate_post()" style="cursor:pointer;border:0" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"><img id="rating_171974_8" src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/stars_crystal/rating_half.gif" alt="8 Stars" title="8 Stars" onmouseover='current_rating(171974,8,"8 Stars")' onmouseout="ratings_off(7.4,8,0)" onclick="rate_post()" onkeypress="rate_post()" style="cursor:pointer;border:0" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"><img id="rating_171974_9" src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/stars_crystal/rating_off.gif" alt="9 Stars" title="9 Stars" onmouseover='current_rating(171974,9,"9 Stars")' onmouseout="ratings_off(7.4,8,0)" onclick="rate_post()" onkeypress="rate_post()" style="cursor:pointer;border:0" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"><img id="rating_171974_10" src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/stars_crystal/rating_off.gif" alt="10 Stars" title="10 Stars" onmouseover='current_rating(171974,10,"10 Stars")' onmouseout="ratings_off(7.4,8,0)" onclick="rate_post()" onkeypress="rate_post()" style="cursor:pointer;border:0" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"> (171 votes, average: 7.43 out of 10) </div><img src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/loading.gif" width="16" height="16" alt="Loading..." title="Loading..." class="post-ratings-image" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy">Loading...

Miltons Pimp My Look

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<!DOCTYPE html><html lang="en"><head><meta charset="utf-8"><meta name="viewport" content="width=device-width,initial-scale=1,maximum-scale=1,user-scalable=no,shrink-to-fit=no"><title>Miltons Pimp My Look</title><link rel="stylesheet" type="text/css" href="https://htlbid.com/v3/barstoolsports.com/htlbid.css"><script async src="https://htlbid.com/v3/barstoolsports.com/htlbid.js"></script><script async src="https://www.caffeine.tv/embed.js"></script><script>window.htlbid=window.htlbid||{},htlbid.cmd=htlbid.cmd||[],htlbid.cmd.push(function(){htlbid.setTargeting("pagetype","blog"),htlbid.setTargeting("authorId","40"),htlbid.setTargeting("Verity_keywords",["look | barstool sports","intelligent kid","milton pimp","go","shirt","red flannel shirt","danny","history","hello","politic","true squid","dr. creepy","roommate connor","weekend","mystery"]),htlbid.setTargeting("Verity_positive","0.22"),htlbid.setTargeting("Verity_neutral","0.78"),htlbid.setTargeting("is_testing","no"),htlbid.pubads().setPublisherProvidedId("PPID-GOES-HERE"),htlbid.layout()})</script><script src="https://d9rde3y35j061.cloudfront.net/script.js"></script><script src="https://htlbid.com/v3/barstoolsports.com/htlbid.js" async></script><script src="https://iframely.barstoolsports.com/embed.js" async></script><style>.union__content{font-family:-apple-system,HelveticaNeue,Roboto,sans-serif;font-weight:400;font-size:18px;color:#5a5b5d;word-wrap:break-word;box-sizing:border-box;padding:0 5px 32px 5px}.union__content p{padding:0;margin:16px 0 0 0}.union__content img{display:block;width:100%!important;height:auto;margin:16px 0 0 0}.union__content video{display:block!important;width:100%!important;height:auto;margin:16px 0 0 0}.union__content .articleAd{text-align:center;margin:16px 0 0 0;background-color:#f5f5f5}.union__content .htlad__container{display:inline-block}.union__content p a{color:#377dc4}.union__content .oembed__wrapper{margin:16px 0 0 0}.union__content blockquote:not(.twitter-video){display:block;margin:16px 0 0 0;padding:4px 12px;border-left:4px solid #77889a;font-style:italic;background:#f0f4f8;text-align:left;border-radius:0 6px 6px 0}.union__content blockquote:not(.twitter-video) p{font-style:italic}.union__content blockquote,q{quotes:none}.union__content iframe{max-width:100%}.union__content .bs-image-hidden{display:none}.union__content div.hq-image{width:fit-content;margin:0 auto}.union__content span.image-attribution,.union__content span.image-attribution a{color:#757575;font-size:12px;font-style:italic;letter-spacing:.1px;line-height:14px;text-decoration:none;padding:0;margin:0}.union__content .bs-videoPlayer .bs-videoPlayer__container,.union__content video-js,.wp-video{width:100%!important;height:0!important;position:relative;padding-bottom:56.25%;overflow:hidden;margin:16px 0 0 0}.wp-video video{width:100%!important;height:100%!important}.hq-image video{width:100%!important;height:100%!important}.union__content .bs-videoPlayer__container>iframe{position:absolute;top:0;left:0;width:100%;height:100%;border:none}@media (prefers-color-scheme:dark){.union__content,body,html{background:#1c1c1c;color:#f1f1f1}.union__content blockquote:not(.twitter-video){border-left:4px solid #367dc4;background:#272c35}}</style><script>window.addEventListener("applicationDidBecomeActive",()=>{document.querySelectorAll(".hq-image video[autoplay]").forEach(e=>e.play())})</script><script>window.htlAdUnitPath="57249056/in-app-iOS/Article-Page_In-Article-Unit",window.htlKeyvalues={authorId:"40",category:"No category",tags:[],brandName:null,brandId:0,pagetype:"standard_post"}</script></head><body class="union__content"><a href="http://boston.barstoolsports.com/random-thoughts/miltons-pimp-my-look-38/attachment/m1-12/" rel="attachment wp-att-120100"><img title="m1" alt src="http://boston.barstoolsports.com/files/2012/11/m11.png" width="292" height="266" sizes="(max-width: 1080px) 100vw, 776px" loading="eager"></a>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<a href="http://boston.barstoolsports.com/files/2013/11/dooley-1.jpg"><img class="alignnone size-large wp-image-171975" alt="dooley 1" src="http://boston.barstoolsports.com/files/2013/11/dooley-1-480x616.jpg" width="480" height="616" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"></a> <a href="http://boston.barstoolsports.com/files/2013/11/dooley-2.jpg"><img class="alignnone size-large wp-image-171976" alt="dooley 2" src="http://boston.barstoolsports.com/files/2013/11/dooley-2-478x640.jpg" width="478" height="640" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"></a> <a href="http://boston.barstoolsports.com/files/2013/11/dooley-3.jpg"><img class="alignnone size-large wp-image-171977" alt="dooley 3" src="http://boston.barstoolsports.com/files/2013/11/dooley-3-480x581.jpg" width="480" height="581" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"></a> <a href="http://boston.barstoolsports.com/files/2013/11/dooley-4.jpg"><img class="alignnone size-large wp-image-171978" alt="dooley 4" src="http://boston.barstoolsports.com/files/2013/11/dooley-4-480x360.jpg" width="480" height="360" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"></a> <a href="http://boston.barstoolsports.com/files/2013/11/dooley.jpg"><img class="alignnone size-large wp-image-171979" alt="dooley" src="http://boston.barstoolsports.com/files/2013/11/dooley-480x640.jpg" width="480" height="640" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"></a>   Reader EmailHello,This is my roommate Connor, aka Dr. Creepy. He is a very intelligent kid when it comes to history and politics and what not but when it comes to putting on clothes it looks like he gets dressed in the dark most of the time. Where he gets some of these shirts he owns is a mystery to all of us. He can’t go a weekend without sporting his go to red flannel shirt with the USA shirt underneath it. And as for the snowman T-Shirt he’s wearing in one of the pictures he legitimately thinks it stylish. Anytime the kid gets dressed and we question what he’s wearing he always says his go to catchphrase “I think it’s just nifty!”. The kids a true squid so please help out this poor bastard and teach this kid how to dress, because at the age of 22 he still has yet to figured it out.<div id="Article-Ad-Placeholder" data-union-ad></div>Thanks,Danny<div class="rating"><img id="rating_171974_1" src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/stars_crystal/rating_on.gif" alt="1 Star" title="1 Star" onmouseover='current_rating(171974,1,"1 Star")' onmouseout="ratings_off(7.4,8,0)" onclick="rate_post()" onkeypress="rate_post()" style="cursor:pointer;border:0" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"><img id="rating_171974_2" src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/stars_crystal/rating_on.gif" alt="2 Stars" title="2 Stars" onmouseover='current_rating(171974,2,"2 Stars")' onmouseout="ratings_off(7.4,8,0)" onclick="rate_post()" onkeypress="rate_post()" style="cursor:pointer;border:0" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"><img id="rating_171974_3" src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/stars_crystal/rating_on.gif" alt="3 Stars" title="3 Stars" onmouseover='current_rating(171974,3,"3 Stars")' onmouseout="ratings_off(7.4,8,0)" onclick="rate_post()" onkeypress="rate_post()" style="cursor:pointer;border:0" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"><img id="rating_171974_4" src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/stars_crystal/rating_on.gif" alt="4 Stars" title="4 Stars" onmouseover='current_rating(171974,4,"4 Stars")' onmouseout="ratings_off(7.4,8,0)" onclick="rate_post()" onkeypress="rate_post()" style="cursor:pointer;border:0" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"><img id="rating_171974_5" src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/stars_crystal/rating_on.gif" alt="5 Stars" title="5 Stars" onmouseover='current_rating(171974,5,"5 Stars")' onmouseout="ratings_off(7.4,8,0)" onclick="rate_post()" onkeypress="rate_post()" style="cursor:pointer;border:0" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"><img id="rating_171974_6" src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/stars_crystal/rating_on.gif" alt="6 Stars" title="6 Stars" onmouseover='current_rating(171974,6,"6 Stars")' onmouseout="ratings_off(7.4,8,0)" onclick="rate_post()" onkeypress="rate_post()" style="cursor:pointer;border:0" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"><img id="rating_171974_7" src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/stars_crystal/rating_on.gif" alt="7 Stars" title="7 Stars" onmouseover='current_rating(171974,7,"7 Stars")' onmouseout="ratings_off(7.4,8,0)" onclick="rate_post()" onkeypress="rate_post()" style="cursor:pointer;border:0" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"><img id="rating_171974_8" src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/stars_crystal/rating_half.gif" alt="8 Stars" title="8 Stars" onmouseover='current_rating(171974,8,"8 Stars")' onmouseout="ratings_off(7.4,8,0)" onclick="rate_post()" onkeypress="rate_post()" style="cursor:pointer;border:0" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"><img id="rating_171974_9" src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/stars_crystal/rating_off.gif" alt="9 Stars" title="9 Stars" onmouseover='current_rating(171974,9,"9 Stars")' onmouseout="ratings_off(7.4,8,0)" onclick="rate_post()" onkeypress="rate_post()" style="cursor:pointer;border:0" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"><img id="rating_171974_10" src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/stars_crystal/rating_off.gif" alt="10 Stars" title="10 Stars" onmouseover='current_rating(171974,10,"10 Stars")' onmouseout="ratings_off(7.4,8,0)" onclick="rate_post()" onkeypress="rate_post()" style="cursor:pointer;border:0" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"> (171 votes, average: 7.43 out of 10) </div><img src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/loading.gif" width="16" height="16" alt="Loading..." title="Loading..." class="post-ratings-image" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy">Loading... </body></html>

<a href="http://boston.barstoolsports.com/random-thoughts/miltons-pimp-my-look-38/attachment/m1-12/" rel="attachment wp-att-120100"><img title="m1" alt src="http://boston.barstoolsports.com/files/2012/11/m11.png" width="292" height="266" sizes="(max-width: 1080px) 100vw, 776px" loading="eager"></a>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<a href="http://boston.barstoolsports.com/files/2013/11/dooley-1.jpg"><img class="alignnone size-large wp-image-171975" alt="dooley 1" src="http://boston.barstoolsports.com/files/2013/11/dooley-1-480x616.jpg" width="480" height="616" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"></a> <a href="http://boston.barstoolsports.com/files/2013/11/dooley-2.jpg"><img class="alignnone size-large wp-image-171976" alt="dooley 2" src="http://boston.barstoolsports.com/files/2013/11/dooley-2-478x640.jpg" width="478" height="640" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"></a> <a href="http://boston.barstoolsports.com/files/2013/11/dooley-3.jpg"><img class="alignnone size-large wp-image-171977" alt="dooley 3" src="http://boston.barstoolsports.com/files/2013/11/dooley-3-480x581.jpg" width="480" height="581" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"></a> <a href="http://boston.barstoolsports.com/files/2013/11/dooley-4.jpg"><img class="alignnone size-large wp-image-171978" alt="dooley 4" src="http://boston.barstoolsports.com/files/2013/11/dooley-4-480x360.jpg" width="480" height="360" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"></a> <a href="http://boston.barstoolsports.com/files/2013/11/dooley.jpg"><img class="alignnone size-large wp-image-171979" alt="dooley" src="http://boston.barstoolsports.com/files/2013/11/dooley-480x640.jpg" width="480" height="640" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"></a>   Reader EmailHello,This is my roommate Connor, aka Dr. Creepy. He is a very intelligent kid when it comes to history and politics and what not but when it comes to putting on clothes it looks like he gets dressed in the dark most of the time. Where he gets some of these shirts he owns is a mystery to all of us. He can’t go a weekend without sporting his go to red flannel shirt with the USA shirt underneath it. And as for the snowman T-Shirt he’s wearing in one of the pictures he legitimately thinks it stylish. Anytime the kid gets dressed and we question what he’s wearing he always says his go to catchphrase “I think it’s just nifty!”. The kids a true squid so please help out this poor bastard and teach this kid how to dress, because at the age of 22 he still has yet to figured it out.<div id="Article-Ad-Placeholder" data-union-ad></div>Thanks,Danny<div class="rating"><img id="rating_171974_1" src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/stars_crystal/rating_on.gif" alt="1 Star" title="1 Star" onmouseover='current_rating(171974,1,"1 Star")' onmouseout="ratings_off(7.4,8,0)" onclick="rate_post()" onkeypress="rate_post()" style="cursor:pointer;border:0" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"><img id="rating_171974_2" src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/stars_crystal/rating_on.gif" alt="2 Stars" title="2 Stars" onmouseover='current_rating(171974,2,"2 Stars")' onmouseout="ratings_off(7.4,8,0)" onclick="rate_post()" onkeypress="rate_post()" style="cursor:pointer;border:0" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"><img id="rating_171974_3" src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/stars_crystal/rating_on.gif" alt="3 Stars" title="3 Stars" onmouseover='current_rating(171974,3,"3 Stars")' onmouseout="ratings_off(7.4,8,0)" onclick="rate_post()" onkeypress="rate_post()" style="cursor:pointer;border:0" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"><img id="rating_171974_4" src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/stars_crystal/rating_on.gif" alt="4 Stars" title="4 Stars" onmouseover='current_rating(171974,4,"4 Stars")' onmouseout="ratings_off(7.4,8,0)" onclick="rate_post()" onkeypress="rate_post()" style="cursor:pointer;border:0" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"><img id="rating_171974_5" src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/stars_crystal/rating_on.gif" alt="5 Stars" title="5 Stars" onmouseover='current_rating(171974,5,"5 Stars")' onmouseout="ratings_off(7.4,8,0)" onclick="rate_post()" onkeypress="rate_post()" style="cursor:pointer;border:0" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"><img id="rating_171974_6" src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/stars_crystal/rating_on.gif" alt="6 Stars" title="6 Stars" onmouseover='current_rating(171974,6,"6 Stars")' onmouseout="ratings_off(7.4,8,0)" onclick="rate_post()" onkeypress="rate_post()" style="cursor:pointer;border:0" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"><img id="rating_171974_7" src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/stars_crystal/rating_on.gif" alt="7 Stars" title="7 Stars" onmouseover='current_rating(171974,7,"7 Stars")' onmouseout="ratings_off(7.4,8,0)" onclick="rate_post()" onkeypress="rate_post()" style="cursor:pointer;border:0" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"><img id="rating_171974_8" src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/stars_crystal/rating_half.gif" alt="8 Stars" title="8 Stars" onmouseover='current_rating(171974,8,"8 Stars")' onmouseout="ratings_off(7.4,8,0)" onclick="rate_post()" onkeypress="rate_post()" style="cursor:pointer;border:0" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"><img id="rating_171974_9" src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/stars_crystal/rating_off.gif" alt="9 Stars" title="9 Stars" onmouseover='current_rating(171974,9,"9 Stars")' onmouseout="ratings_off(7.4,8,0)" onclick="rate_post()" onkeypress="rate_post()" style="cursor:pointer;border:0" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"><img id="rating_171974_10" src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/stars_crystal/rating_off.gif" alt="10 Stars" title="10 Stars" onmouseover='current_rating(171974,10,"10 Stars")' onmouseout="ratings_off(7.4,8,0)" onclick="rate_post()" onkeypress="rate_post()" style="cursor:pointer;border:0" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy"> (171 votes, average: 7.43 out of 10) </div><img src="https://cdn.barstoolsports.com/wp-content/plugins/wp-postratings/images/loading.gif" width="16" height="16" alt="Loading..." title="Loading..." class="post-ratings-image" sizes="(max-width: 1080px) 100vw, 776px" loading="lazy">Loading...

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