I think the easiest way for me to describe the way I style something that is a little edgier or trendier than my typical style, is that I wear a 'normal' outfit and then add in the trend.
So, for example, this outfit in the above photos is super basic. It's a a simple cabled crewneck sweater, cashmere scarf, dark denim and ballet flats. But, when you throw on the leather jacket, it instantly becomes trendier and, in my opinion, chicer. This is also a great example of a way to incorporate a leather jacket into your wardrobe during the day.
I used to only wear it out at night with my friends when we would go to bars, but the jacket it surprisingly warm and I've started to rotate it into my daytime wardrobe, too! I wore this after work to grab dinner and drinks! How do you style a leather jacket during the day? Have a fabulous day!