According to The Old Waldorf-Astoria Bar Book, there are two versions of the Orange Blossom: one neat and one on the rocks.
In the 1935 book A.S. Crockett says that the Orange Blossom No. 1 (neat) was likely created by "some young bridegroom or other who wanted something novel to use at his final stag party." The sweet vermouth of this cocktail takes some of the acidity out of the drink, making it very nice.
Crockett's recipe for the Orange Blossom No. 2 (or Adirondack), which excludes sweet vermouth, is built in a "bar glass," and either an old-fashioned or highball glass with ice will work. It also calls for 1:1 gin and orange juice so you want to keep the glass small or go with a little more juice to keep the alcohol content manageable.