Green’s Dictionary of Slang

1. in the height of fashion, smart, fine.

1791		‘Song’ in New Vocal Enchantress 33: Hum’d, and them humbugg’d, twaddy, tippy, poz / All have had their day, but now must yield to quoz.
1821		National Advocate (N.Y.) 3 Aug. 2/2: Blue coat fashionably cut; red ribbon and a bunch of pinchback [sic] seals; wide pantaloons; shining boots, gloves, and a tippy rattan.
1824		N.Y. Eve. Post 20 Apr. 2/4: His tippy coat, his blue silk sham, his cossack pantaloons, his corsets and shammy gloves, were all restored.
1841		‘F.L.G’ Swell’s Night Guide K4: Tippy As it Ought to Be.
1847		Thackeray Punch’s Prize Novelists: Crinoline in Burlesques (1903) 216: He had the tippiest Jane boots.

2. clever, ingenious.

1863

M. Dods Early Letters (1910) 344: I am now going to lend her the antidote — a tippy little bit of criticism by Pressensé .