I really loved my Koss PortaPros. Stylistically, they look like they were designed in the early 80s and just left there, but they sounded great. Additionally, the cord was plenty long without being too long, and the ear support pad business made them really comfortable. I was kind of afraid to wear them in public, though. I don't think they're any uglier than the Grados, though. They're both from different eras. The PortaPros are usually around $40, so cheaper than the Grados. Supposedly, the same drivers are in the KSC series, the KTXPRO1 and the SportaPro which are all cheaper and arguably look better than the PortaPro. The KTXPRO1 and the SportaPro usually go for less than $20. The KSC series ones all clip over the ear like some weird earmuffs, and the Sporta Pro kind of goes around the back of your head, so they kind of meet your needs there.

Right now I have the Sennheiser PX100 which are around ~$50, sound great, and look quite decent. Of the cheap Sennheisers, the PX200 might be better for you since it's closed, though.