there are no headphones really that you dont look dorky walking around with especially higher end cans. I have some entry level cans and soem more expensive ones and i wouldnt want to walk around with them on a regular basis anywhere mind you i drive so i dont walk much. For under 100 bux i would recommend alot of different cans then you looked at. Sennheiser 500 series are crap i have the 500s and the 555s and the 595s they all get used for computer gaming which is probably their only strong suit. I would recommend Grado sr60 or 80s, or even the igrados if you want to look less of a dork. AKG 240s are around the 100 dollar mark and are a VERY neutral audiophile can, suprise suprise since they are one of the most popular studio monitor headphones, honestly sennheiser doesnt really make a good can under 100 cept maybe the hd212 course not great on the slick looking factor either. Ultrasone makes some descent cans in that price range and also a ipod behind the
head version called the icans which are really neat looking. IEMS are your best bet if your looking for looks, but like you said no bass in the sub 100 range really. I have the beats by dre IEMS and they arent worth the extra dough so pat yourself on the back for not buying them. Great sounding IEMS but the premiums that cost a fraction of the price would do that job marginally as well. Unfortunately for any real audiophile headphone your going to be in the 250-500 dollar range for entry level up to thousands for high end stuff, and quite frankly theres not many pretty ones out there. Ultrasone ED9 comes to mind in slick looking cans for about a grand but there is very few.
good luck in your search