Check out the Sidi On road sympatex boots. It has extra leather where the shifter hits your boot...
http://www.motorcycle.com/mo/mcbeware/sympatex.htmlI have a pair that I have been wearing for about 7 years. It's about time for new soles on mine. Scootergrrl just got a pair and loves them.

 

I'm like bensonjv. I have the Harley boots(and have had for 6 years - 70K+ miles) and the toe is scuffed from shifting. I have the Iso-peg from Kuryakyn. Mine hasn't started cracking yet because I hit them every so often with some saddle soap and good polish.

 

Better boots or heel-toe shift.

 

I had the same problem with the heritage, shifter ruining boots. A true riding boot will fare better, but still scuff eventually. I wear wesco out on the road but in town I often wear Lariat for daily wearor some other dress boots for going out. I put on a smooth shifter peg and it totally solved the problem. (stock shifter has those ridges) Anything smooth up on the custom stuff wall at your closest dealer.The bike and boots are ten years old now with no scuff. Shoe polish too, get a can-O-Kiwi, givethem a clean and shine just like you do your bike. Ten years now, the Lariats have the patina of age, but still look look great, the Wesco show no wear whatsoever after about 20,000 miles on them alone, they are just now starting to get really comfortable.....they cost ALOT, but you only buy them once.
I bought a Sportster this year for ripping around in the city, same thing, the shifter started eating a hole in my dress boots, changed peg, solved problem.

 

Me again....correction, Ariat boots not "Lariat".......great boots, very comfortable, good daily wear

 

Either way you are making a statement about what you are: A Biker!

 

Slip a condom over the shifter..............Plus youll always have one handy

 

I wear a pair of boots that don't get the scuff marks. I say duct tape up the boots once the hole starts.

 

I have worn the same pair of Millwuakee Boots for over 18,000 miles on my Ultra, Plus 16,000 on my Fat Boy before that,and you can not see any Scuff. I don't use the heel shifter, but I do clean my boots and even put a bit of polish on them once every other month or so..

Clean them with Saddle Soap, Polish them with a good Paste polish. I treat them like I did my Air Force Combat Boots, I keep them looking good...and never see any scuffs..

 

Just cause they're Harley ... don't make 'em good. I've never had your problem ... panheads, shovelheads, evos, twinkies. My guess is your boots need replaced.