I saw them around but never tried them myself. So, i can't help you there.
If he looks specifically for street style, i really don't think KSC55 is really difficult to beat. I think because of its fit, i feel it's even more balanced (read less boomy) than my Portapro. Especially, when you can get one for $12.55. Well... you can get 2 to get free shipping and keep a pair for yourself. I just don't use it that much because i hate putting on and taking off streetstyle.
My trick for KSC55: use hairdryer and blank spindle of CD to help stretch its headband. Warm it up and stretch it to perfect shape. You probably want to cover its drivers a bit with washcloth or something, just to make sure that you don't burn (literally) your drivers.
If he still hesitate about his choice, tell him that "What kinda magic headphones you want for your $30?" and go get a new friend.
I am using the Sony MDREX71's that I bought from Amazon.com. The sound is pretty good for the $30 I paid. The isolation is okay, you might hear some sound through them. Pretty good since you don't want to walk in traffic not hearing anything. The trick to bring out the best possible Bass is to find the right size plugs that fits. I was using the Medium size and wasn't getting any bass at all. Also they were falling out of my ears. Once I used the smallest size, which felt awkward at first, the bass got much louder and it fitted perfectly.
Mids are best so far in terms of canal phones for me, but highs could be better. Bass was what I was looking for and these Sonys do the job. Suitable for electronica and light rock music. I use these UNamped but they are easily driven.
The headphone wire is perfect for portable use, its extremely short - ideal for remotes. It also comes with a long extension cord if you don't use a remote. Some people may not like the right side having the longer cable, but I just wrap it around the back of my neck. Also comes with wire adjuster and headphone case!