So, last week I decided to wear an old leather jacket I've had for a long time, bought long before my taste was even close to what I prefer today. It still fits quite well and is an ideal fall jacket warmth-wise. This whole combo was just for a brief walk to the groceries, and perhaps more to study the jacket than to look stylish.
To go with the jacket I picked my Litchfields, olive chinos (mistake) and a gingham checked flannel shirt. Now, I don't really think this one worked too well, and I'm going to tell you why. First of all, I actually quite like the jacket. It's not the most beautiful leather jacket, but it isn't terribly ugly either. It fits well and the color is rather beautiful. It also goes well with the nice (and super comfortable) shirt and the boots.
The problem here are the pants (which I chose because everything else was in the washing machine). It's not even the color, but the cuffs. Actually after taking the shots I folded them quite nicely achieving a more rugged feel to them. Still, a bit more worn and less dressy chinos or jeans and I'd say this one would be totally OK for a fall day or even not-so-cold winter day.
So, I'm definitely not a leather jacket fan, but sometimes stepping out of your boundaries and experimenting with different stuff does bring new ideas and helps you evaluate your current style better. You try new things, see if they fit you, and then make decisions whether you will or won't do the same thing twice.
I'll most likely wear my leather jackets more than once this winter.