This question seems to come up almost weekly and so I will give you my opinion once again.
After CCW carrying for 36 years I would NOT recommend trying to carry a M586! Great gun, just too big, too heavy and too bulky. You will wind up leaving it at home or in places you shouldn't just to get it off your body. Not saying you couldn't do it once in a while, but it is just not practical for dedicated CCW.
I'd invest in a J Frame if you want a CONCEALABLE and PRACTICAL CCW Wheel Gun, or if you would like a 6th shot the Colt Dick Specials are still out there and barely larger or heavier than a Chief's Special. There are also plenty of Auto's that would fit the bill if you prefer, but a M586 is IMO the wrong way to pursue CCW. YMMV.
What I've found to be the absolute best OWB carry is a Kramer Horsehide Belt Scabbard with the FBI cant, a 1 1/4" horsehide belt and matching ammo dump pouch. Not cheap - but the BEST Ive ever used no matter what gun I am carrying. J-Frames (or Colt Dick Spl's) are small enough and light enough that they can be carried in any type of holster you choose such as IWB, OWB, Ankle, Shoulder and Pocket. The larger guns can not.
If you still choose to carry your M586 I believe to will find out just like the majority does (the hard way as I did too) that seriously carrying a concealed weapon every day is a commitment, a matter of comfort and practicality. An L Frame isn't gonna fit that bill - sorry to say.