Omari commenced his legal career in 2005, interning at Clarke Gittens Farmer during his summer vacation while pursuing a Bachelor of Law (LLB) at the University of Kent, Canterbury, England. After graduating with Honours, he pursued a Bar Vocational Course at the College of Law of England and Wales and in 2008, he was called to the Utter Bar of England and Wales at the Honourable Society of the Middle Temple. The following year he commenced studies at the Hugh Wooding Law School and was admitted to the Barbados Bar in 2010.

During his years at Clarke Gittens Farmer, Drakes achieved incredible milestones and significantly contributed to numerous projects and initiatives. Currently a Deputy Chair of the Employments Rights Tribunal as well as the longest serving member, Omari has also managed the Clarke Gittens Farmer UWI Moot Competition on behalf of the Firm for over a decade.

Omari has provided and continues to provide training on Labour Law related matters and has also represented the Firm at speaking engagements for the Human Resource Management Association of Barbados and the Caribbean Society for Human Resource Professionals.