So you could start by alkylating with either friedel crafts acylation (reduce) or alkylation. Then Brominate the benzylic carbon with NBS and uv light. Next do an elimination with sodium tert-butoxide to get the double bond. This molecule(styrene) can now be reacted with B2H6, H2O2, and NaOH to give the anti-markovnikov product which is 2-phenylethanol. If you want 1-phenylethanol just use H2O, H+ instead of B2H6, H2O2, and NaOH.
Hope this helps!