It is pretty full-on, so the rest of the outfit needs to be pretty subtle and classic. You are going for a preppy / varsity look with this.
I would wear it with a plain white t shirt, sand coloured chinos and some tan loafers. Some kind of smart, classic hairstyle is an important part of this look too.
This will look really good if you get it right- the key is simplicity in the rest of the outfit.
I have a hard time wearing my varsity jacket too. I have this one:
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