Listen, everyone will tell you that you need to wear attitude with your leather. In case you can't tell, life is good in a leather jacket. Relax, you've made it. Enjoy your cool life. At Men's Fashion Magazine there's big talk that leather jackets are all about the rebel, the punk, the generally tough guy who will kick your ass if you look at them funny. This is patently untrue. Though they trace the rise of the leather jacket from the 1950's to now, there has been leather and leather wearers who are free in other ways.
That's what the leather jacket is all about, folks! Freedom, baby! I remember when I got my first leather jacket. I grabbed it at a garage sale festival (they exist) and it was the smoothest, sexiest thing I had ever seen. I can wear it out with almost anything and turn heads. If only the weather would cooperate.
All that being said, let's get down to the bread and butter of style.
If you haven't figured out how to pick one yet, head over to this post on finding the best bang for your buck.
Don't laugh! Not everybody opts for a shirt. Sometimes no shirt can be sexy.
Anyway, pick your damn shirt to match the color of your leather. I don't mean wear black on black, which you can do, but just be smart about it. No neon green unless you're at a rave.
If you've got a bomber jacket, grab some casual pants: jeans, leather, or some other casual two-leger. See those jeans above? That works. Check out the dress pants under CONFIDENCE too. you'll need it to rock dress pants and jeans. Trust me, once they're in front of you you'll be confused. Here's a rule: if you are worried about the fashion police bothering you, don't. If you don't care, are free, then do it.
Let's break this down quickly for you. The leather jacket has a ton of ornaments. It has EXTRAS. That's a way of saying 'Yo, I AM' in a certain way. This jacket would not work with dress pants and shoes because they are form different worlds. Think of yourself as an actor; you have to stick to your role. So before you go out, choose who you want to be and 'role' with it.
If this hasn't helped you, check out the Art Of Manliness as they explain not only why you should buy, but the several types of leather jackets. Stay free.