30. The Leather Biker Jacket — Even if you're not a James Dean type, we think it's wise to invest in a moto jacket. You'll gain instant street cred without looking like a poser in some of the new options that have just come on the market, plus they give you some biceps you never knew you had.  

AllSaints Convoy Leather Biker Jacket, $495, available at AllSaints; Yves Saint Laurent Lightweight Leather Biker Jacket, $4550, available at Mr. Porter.