Welcome to the forum Corey. As you might have noticed by the lack of responses, hard bags on a Street Bob hasn't been done much. My thinking is smaller bags would look best. HD has some nice looking hard bags for Sportsters. Leather look for $700, or gloss for $1,300 (ouch). Take a look, and come back and let us know what you ended up doing. [URL="http://exit.hdtimeline.com/postid333313"]Rigid Leather Locking Saddlebags | Harley-Davidson USA
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I put the rigid lockable bags on my super glide. I think they look really nice and I'm happy with them. The price of $700 is a little steep but I was able to get a new set on ebay for around $580. It's expensive either way you look at it but it's nice to have the additional storage.
Hard bags are nice but pricey. If you don't mind a bit of leather maintenance, Leatherneck Jims , Leatherworks and others are a nice alternative at approx. 1/2 the cost depending on features and style you order, even hard to fit bikes like my Sporty
Check out National Cycle hard bags they can be viewed at Tucker Rocky-Leader in Wholesale Distribution of Powersports Parts, Accessories and Apparel have a set on my Dyna and they look great. My bike was gloss black so I just openend the box and mounted them on the bike. If your bike is not black they are tottaly paintable to match. They run about $730. for the complete set including mounting hardware.
Good Luck
I have the same bike and I have Boss Bags. Check them out. Pricey, but you get what you pay for. Hard inner shell and nice leather outside. Mine quik detach and they lock to the bike.