In choosing a leather jacket, the crucial element to consider is fit. I'd rather see you in a pleather number from H&M than one of those ridiculously huge jackets guys often wear that look like they could fit a small family underneath. To demonstrate how important fit is, Tony Martignetti and I shot this video comparing his old leather jacket to the new one we bought together. Things to look for when shopping for a well-fitting leather jacket: high cut armholes, shoulder seams resting on your shoulders, trim fit though the torso and sleeves hitting at the base of your wrist (Tony likes his sleeves slightly long, to accommodate sports jackets and sweaters. If he wanted to get those sleeves shortened, I recommend leather specialists like Art Bag and Modern Leather Goods here in NYC.). Tony is the founder of Martignetti Planned Giving Advisors. Tweet him here and check out his weekly radio show here.