I have a Ruger SP101 .357 with a 2 1/4" barrel, and want to carry it on the ankle. I have been using a Galco Cop elastic band ankle holster, and it is working ok. I just want something a little nicer. The weight of the gun is not an issue for me as I am a Huge fat ass and wear baggy jeans (6'2 290 pounds) I'm leaning towards a Galco Ankle glove but wonder if there are more premium type ankle holsters out there? I know IWB carry is better, but my Browning HP resides there in a Milt Sparks VM II, the Ruger is for back up or carry when I'm too lazy to strap up the HP.

It is quite expensive ($198) but I am holding out for a Kramer ankle holster.  
kramerleather.com/productDetail.cfm?productID=1&categoryID=29

//Homer voice on// Mmmmmm sheeps wool... mmmmm //end voice//

I've owned a number of ankle holsters over the years.  I'm not generally a fan of Galco, but I have to admit that the ankle glove is the most comfortable I've worn.  I don't have one at the moment, but I wouldn't hesitate to buy another if I owned a gun they made a holster for.

I'm currently using one from this guy:
http://www.klnullholsters.com/

The quality is excellent, and the fit to the gun is outstanding.  I think I like the neoprene and fleece of the galco for long term comfort a bit better, but it can be too warm if you're in a hot climate.  

I have the Galco for a G27. Have used it for years and love it. I use it as a back up carry gun. I also switch out between that and a Galco SOB holster.

I'd really recommend Alessi's Ankle holster.  I have one for my Colt Det. Special and it's very comfortable.

Ankle Gloves are great and definately plus one for Alessi.

I'm very happy with my two Alessi's.

I wear a Galco Ankle Glove with a S&W 642 all day, everyday, and do not even know it is there.  Excellent holster for the money.

I have a Mitch Rosen and I can recomend it very highly.