Garb: Budget Mad Man

If you're trying to get your own Sterling Cooper Draper Price off the ground, you don't yet have the cash flow to style like 1964. Dress like Don without going bankrupt, and instead spend a few extra dollars on the whiskey.

Coat ($80), jacket ($70) and pants ($40) by H&M; shirt ($65) and shoes ($285) by J.Crew; tie ($24) by Gap.