When I think of sportswear, Sears, Roebuck is not a brand that immediately pops into my mind. But in this case, Sears made a really sweet little skating ensemble, marketed under their Kerry-Teens label.
Kerrybrooke was the Sears, Roebuck house brand from the late 1940s until the 60s. And even though you can see the little R in a circle symbol, meaning that the name was a registered trademark,I could find no trace of the Kerry-teen name on the US trademark database.
The only reference to Kerry-Teen I could find in my sources was in a 1958 Sears, Roebuck catalog that I own. Online, I found catalog references to the Kerry-Teen name from 1956 to 1961.
The set that I bought falls squarely within that time frame. Consisting of a short skating skirt and a sleeveless top, this could be either late 1950s or early 1960s. Fashion does not obey the arbitrary assignment of decades that we try to impose upon it.
The skater is appliqued onto the flannel skirt. What makes it really special are the pom-poms on the tops of each skate. 
The skirt is lined with red acetate, which made for fancy twirling on the ice.
I could not decide if the half-belt which is attached to the top goes to the front or to the back. I’m betting that one could have also ordered a red turtleneck sweater to go under the top.
I was really happy to get this because it is a set, and not just the individual pieces. It is getting harder and harder to find matched pieces of sportswear, and though the skirt is really great, it helps to better visualize how it was worn when the top is added.
The Vintage Traveler 