The Collaborative International Dictionary of English v.0.48:

Rakish \Rak"ish\ (r[=a]k"[i^]sh), a.
   Dissolute; lewd; debauched.
   [1913 Webster]

         The arduous task of converting a rakish lover.
                                                  --Macaulay.
   [1913 Webster]

The Collaborative International Dictionary of English v.0.48:

Rakish \Rak"ish\ (r[=a]k"[i^]sh), a. (Naut.)
   Having a saucy appearance indicative of speed and dash.
   --Ham. Nav. Encyc.
   [1913 Webster]

WordNet (r) 3.0 (2006):

rakish
    adj 1: marked by up-to-dateness in dress and manners; "a dapper
           young man"; "a jaunty red hat" [syn: dapper, dashing,
           jaunty, natty, raffish, rakish, spiffy,
           snappy, spruce]
    2: marked by a carefree unconventionality or disreputableness;
       "a cocktail party given by some...raffish bachelors"- Crary
       Moore [syn: devil-may-care, raffish, rakish]

Moby Thesaurus II by Grady Ward, 1.0:

48 Moby Thesaurus words for "rakish":
   abandoned, brave, bravura, braw, breezy, chic, chichi, dandy,
   dapper, daring, dashing, debauched, debonair, devil-may-care,
   dissipated, dissolute, dressy, elegant, exhibitionistic,
   fashionable, fast, flashing, flashy, flaunting, foppish, free,
   frilly, frothy, gallant, gay, glittering, jaunty, jazzy,
   licentious, profligate, raffish, rakehell, rakehellish, rakehelly,
   showy, smart, snazzy, splashy, splurgy, sporty, spruce, unbridled,
   wild