Se você tiver o SQL 2008, poderá usar o novo tipo de dados hierarchyid:
WITH Items (ItemNumber) AS (
SELECT '1' UNION ALL SELECT '1.1' UNION ALL SELECT '1.1.1'
UNION ALL SELECT '10' UNION ALL SELECT '11' UNION ALL SELECT '2'
UNION ALL SELECT '2.1' UNION ALL SELECT '20' UNION ALL SELECT '3'
UNION ALL SELECT '30'
)
SELECT *
FROM Items
ORDER BY Convert(hierarchyid, '/' + ItemNumber + '/');