If you haven't figured out that the Icon Garage Team's loves the venerable Sportster - than you haven't been paying attention. Hella durable, mechanically simple, awesome sound, relatively cheap, & full of American soul. The Icon recipe for cool Sportstering is quite simple;
1. Pick one up for cheap from your local tweeker (no teeth, no title, no keys, no problem)
2. Shitcan every last bit of HD billet chrome garbage attached to it (and there will be plenty)
3. Spend countless hours on Ebay finding late model Japanese sportbike componentry (we prefer R6 and ZX parts)
4. Find someone with a metal lathe and befriend them with room temperature PBR (or two hundred rounds of .223 reloads)
5. Get a really nice DeWalt angle grinder, oxy-acetylene torch, and a second hand mig welder (otherwise known as life skills)
6. Commence chopping that fuking Sportster to within an inch of it's life (you'll know when you've gone to far)
7a. If it turns out cool - Contact the Bastards at Quad Cam for an invite to Deals Gap for the third annual Bastard Bash rally
7b. If it turns out uglier than homemade sin - part it out on Ebay and speak of this sad episode no more
Though we don't approve of riding without protective gear we do approve of flogging your Sportster at all times. A flogged Sportster is a happy Sportster.