Blame James Dean -- he's the one that started all of this. The classic, semi-rockabilly look has existed for years, and it's just as popular as it ever was. Women seem to like the rough edges portrayed by this look, and tend to prefer men stick to either classic or safe-ish styles when doing so -- overly modern jacket styles or cuts can look overly trendy, if not try-hard.
The Takeaway: Get a well-fitting leather jacket. A well-made leather jacket from a top-tier leather goods manufacturer like Schott will last you a lifetime.
How to Perfect It: Depending on the jacket and its construction, you may want to initially purchase a leather jacket undersized -- the jacket will stretch to your body as you wear it more.
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Had a pair of Carhartt B-11 jeans (dark blue) and they were wonderful. The only real downside about the Carhartt line is that you won’t likely find them when you Google ‘jeans.’ You have to go to ‘workclothes.’